1-Iodoadamantane
(Synonyms: Adamantyl iodide) 目录号 : GC250041-Iodoadamantane (Adamantyl iodide) is a chemical.
Cas No.:768-93-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
1-Iodoadamantane (Adamantyl iodide) is a chemical.
| Cas No. | 768-93-4 | SDF | Download SDF |
| 别名 | Adamantyl iodide | ||
| 分子式 | C10H15I | 分子量 | 262.13 |
| 溶解度 | DMSO: 52 mg/mL (198.37 mM);; | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.8149 mL | 19.0745 mL | 38.149 mL |
| 5 mM | 0.763 mL | 3.8149 mL | 7.6298 mL |
| 10 mM | 0.3815 mL | 1.9075 mL | 3.8149 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Electrosynthetic reduction of 1-Iodoadamantane forming 1,1'-biadamantane and adamantane in aprotic solvents: insonation switches the mechanism from dimerisation to exclusive monomer formation
Ultrason Sonochem 2007 Jul;14(5):502-508.PMID:17224295DOI:10.1016/j.ultsonch.2006.11.007.
The combination of ultrasound and electrochemistry -sonoelectrochemistry can produce a variety of effects within an electrochemical system including enhanced mass transport, in situ cleaning of an electrode surface, diminution of the diffusion layer, and possible induction of new reactions by sonochemical enhancement of follow-up reactions post-electron transfer. Herein, we show that ultrasound provides a useful extra dimension to electrosynthesis via a switch in the sonoelectroorganic mechanism in which dimerisation is disfavoured by virtue of convective mixing promoted by insonation. Under 'normal' voltammetric conditions the reduction of 1-Iodoadamantane at a silver cathode in tetrahydrofuran (THF) and acetonitrile (ACN) involves a single electron forming a mixture of monomeric and dimeric products; 58%/THF, 50%/ACN adamantane and 39%/THF, 50%/ACN 1,1'-biadamantane, respectively. However, under the conditions of insonation using a 10 kHz transducer, a single product is formed exclusively; 93%/THF, 96%/ACN adamantane. The effect of insonation upon the voltammetry at a silver macroelectrode is shown and compared to that under silent conditions. In addition, the previously observed characteristic series of oxidation and adsorption peaks following reduction of 1-Iodoadamantane are reduced in magnitude under insonation. Overall, this work shows that the effect of insonation can switch the mechanism of follow-up chemical processes - favoring the formation of a monomer.
S(RN)1 Reactions of 7-Iodobicyclo[4.1.0]heptane, 1-Iodoadamantane, and Neopentyl Iodide with Carbanions Induced by FeBr(2) in DMSO
J Org Chem 1996 Mar 8;61(5):1645-1649.PMID:11667031DOI:10.1021/jo9509566.
There was no reaction of 7-iodobicyclo[4.1.0]heptane (7-iodonorcarane, 1) (exo-endo ratio of ca. 1) with acetophenone enolate ions 2 in DMSO at 25 degrees C; however, with the addition of SmI(2) or FeBr(2) and under the same experimental conditions, the substitution product 3 was obtained in 9% and 72% yields, respectively, with an exo-endo ratio of ca. 16 similar to the product ratio from photostimulated reactions. Thus, it seems that 7-norcaranyl radicals are intermediates of these reactions. With FeBr(2) at 60 degrees C the yield of 3 was as high as 90%. Reactions of 1 with the enolate ion of 2-naphthyl methyl ketone 4 induced by FeBr(2) gave substitution product 5 in 60% yield (96% of it the exo isomer). In competition experiments, 4 was 1.7 times more reactive than 2, and the anion of nitromethane (7) was 6.5 times more reactive than 2 toward 7-norcaranyl radicals. The reactions of 1-Iodoadamantane (9) and neopentyl iodide (11) with carbanion 2 induced by FeBr(2) gave the substitution products in 85% and 92% yields, respectively. These observations indicate that all these reactions induced by FeBr(2) occur by the S(RN)1 mechanism.
Regiochemistry of the photostimulated reaction of the phthalimide anion with 1-Iodoadamantane and tert-butylmercury chloride by the S(RN)1 mechanism
J Org Chem 2002 Feb 8;67(3):1012-5.PMID:11856054DOI:10.1021/jo010756w.
The photostimulated reaction of the phthalimide anion (1) with 1-Iodoadamantane (2) gave 3-(1-adamantyl) phthalimide (3) (12%) and 4-(1-adamantyl) phthalimide (4) (45%), together with the reduction product adamantane (AdH) (21%). The lack of reaction in the dark and inhibition of the photoinduced reaction by p-dinitrobenzene, 1,4-cyclohexadiene, and di-tert-butylnitroxide indicated that 1 reacts with 2 by an S(RN)1 mechanism. Formation of products 3 and 4 occurs with distonic radical anions as intermediates. The photoinduced reaction of anion 1 with tert-butylmercury chloride (10) affords 4-tert-butylphthalimide (11) as a unique product. By competition experiments toward 1, 1-Iodoadamantane was found to be ca. 10 times more reactive than tert-butylmercury chloride.
Reactions of 1,3-Dihaloadamantanes with Carbanions in DMSO: Ring-Opening Reactions to Bicyclo[3.3.1]nonane Derivatives by the S(RN)1 Mechanism
J Org Chem 1997 Jun 27;62(13):4260-4265.PMID:11671745DOI:10.1021/jo9620728.
The reactions of 1,3-dihaloadamantanes with various carbanionic nucleophiles were studied. Potassium enolates of acetophenone (2) and pinacolone (10b) and the anion of nitromethane (10a) reacted with 1,3-diiodoadamantane (1a) in DMSO under photostimulation by a free radical chain process to form a 1-iodo monosubstitution product as an intermediate, which undergoes concerted fragmentation to form derivatives of 7-methylidenebicyclo[3.3.1]nonene (3 and 11). This reaction does not occur in the dark at 25 degrees C, and the photostimulated reaction is partially inhibited by p-dinitrobenzene. 1,3-Dibromoadamantane (1b) and 1-bromo-3-chloroadamantane (1c) also reacted under irradiation with 2, although more sluggish than 1a, also giving the 7-methylidenebicyclo[3.3.1]nonene derivative 3. When a nucleophile was used without acidic hydrogens in the alpha-position, such as the enolate ion of isobutyrophenone (16), in order to inhibit the ring opening of adamantane, it reacted under irradiation with 1a to give the products adamantane, 1-Iodoadamantane, monosubstituted 17, 1-iodo-monosubstituted 19, and disubstituted 20. Their distribution depended on the experimental conditions. In these reactions, 1-Iodoadamantane and 19 were intermediates. For reactions involving the radical anion intermediate of the 1-iodo monosubstitution product, the intermolecular ET to the substrate was observed to be much faster than intramolecular ET to the C-I bond.
Fluorescent quenching of the 2-naphthoxide anion by aliphatic and aromatic halides. Mechanism and consequences of electron transfer reactions
J Org Chem 2003 Mar 21;68(6):2362-8.PMID:12636403DOI:10.1021/jo026518y.
The fluorescent excited state of the 2-naphthoxide ion (1) is quenched by aliphatic and aromatic halides according to an electron-transfer mechanism, with generation of the corresponding alkyl and aryl radicals by a concerted or consecutive C-X bond fragmentation reaction. Whereas bromo- and iodobenzene follow a concerted ET mechanism (C-X, BDE control), 1-bromonaphthalene exhibits a stepwise process (pi LUMO control). The photoinduced reaction of anion 1 with 1-Iodoadamantane (2) in DMSO affords substitution products on C3, C6, and C8, 1-adamantanol, 1-adamantyl 2-naphthyl ether, and adamantane (3.2, 13.2, 12.2, 2.8, 2.5, and 14.1% yields, respectively). A complex mixture is also observed in the photochemical reaction of neopentyl iodide (3) with anion 1, which renders substitution on C1, C3, C6, C8, and 2-naphthyl neopentyl ether (8.1, 1.3, 19.1, 31.1, and 2.8% yields, respectively). The absence of reaction in the dark and the inhibition of the photoinduced reaction by the presence of the radical traps di-tert-butylnitroxide (DTBN) and 1,4-cyclohexadiene are evidence of a radical chain mechanism for these substitutions. On the other hand, only coupling at C1 is achieved by the photostimulated reaction of anion 1 with iodobenzene (5), to afford 41.9% of 1-phenyl-2-naphthol and 5.4% of disubstitution product. The regiochemistry of these reactions can be ascribed to steric hindrance and activation parameters.