1-(Cyanmethyl)-1-hydroxy-4-tert.-butylcyclohexan | 71750-16-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-(Cyanmethyl)-1-hydroxy-4-tert.-butylcyclohexan
• 英文别名: 2-(4-Tert-butyl-1-hydroxycyclohexyl)acetonitrile
• CAS: 71750-16-8
• 化学式: C₁₂H₂₁NO
• 分子量: 195.305
• InChiKey: BJQBPFJSFWOTQC-UHFFFAOYSA-N

物化性质

• 沸点：
  316.0±15.0 °C(Predicted)
• 密度：
  0.981±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(Cyanmethyl)-1-hydroxy-4-tert.-butylcyclohexan 在 氢氧化钾 、 18-冠醚-6 作用下， 以 乙腈 为溶剂， 生成 2-(4-tert-butylcyclohexylidene)acetonitrile
  参考文献：
  名称：

  Direct synthesis of .alpha.,.beta.-unsaturated nitriles from acetonitrile and carbonyl compounds: survey, crown effects, and experimental conditions

  摘要：

  DOI：

  10.1021/jo00393a037
• 作为产物：
  描述：

  (氰基甲基)氯化铈(III) 、 4-叔丁基环己酮 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以96%的产率得到1-(Cyanmethyl)-1-hydroxy-4-tert.-butylcyclohexan
  参考文献：
  名称：

  Formation and efficient addition of cerium(III) derivative of acetonitrile to ketones

  摘要：

  The cerium(III) derivative of acetonitrile undergoes addition with ketones efficiently. It adds effectively to hindered ketones and gives 1,2-adduct exclusively with conjugated enones.

  DOI：

  10.1016/0040-4039(91)80061-a

文献信息

• Reaction of the Electrogenerated Cyanomethyl Anion with Carbonyl Compounds: A Clean and Safe Synthesis of β-Hydroxynitriles
  作者：Gabriele Bianchi、Marta Feroci、Leucio Rossi

  DOI：10.1002/ejoc.200900527

  日期：2009.8

  The electrogenerated cyanomethyl anion reacts with carbonyl compounds to yield the corresponding β-hydroxynitriles in moderate to high yields. The reported methodology is very clean and safe, avoiding the use of any classical base or catalyst. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  电生成的氰基甲基阴离子与羰基化合物反应，以中等至高产率产生相应的 β-羟基腈。报告的方法非常干净和安全，避免使用任何经典碱或催化剂。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Naoto Tominaga、Hiroshi Morita

  DOI：10.1021/jo00052a036

  日期：1992.12

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.
• Dobrev, Alexandre; Ivanov, Christo; Lattes, Armand, Bulletin de la Societe Chimique de France, 1987, # 6, p. 1084 - 1088
  作者：Dobrev, Alexandre、Ivanov, Christo、Lattes, Armand、Bon, Maryse

  DOI：——

  日期：——
• SmI2-mediated nitrile aldol reaction
  作者：Andrei Caracoti、Robert A Flowers, II

  DOI：10.1016/s0040-4039(00)00348-8

  日期：2000.4

  The SmI2-mediated coupling of alpha-bromoacetonitrile and alpha-bromopropionitrile with aliphatic ketones and aldehydes produces beta-hydroxynitriles in good yields. Reactions typically proceed with little diastereoselectivity, but selectivity enhancement occurs with the addition of tetra-n-hexylammonium bromide. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Stereochemie et facteurs orbitalaires—II
  作者：M. Bellassoued、F. Dardoize、F. Gaudemar-Bardone、M. Gaudemar、N. Goasdoue

  DOI：10.1016/0040-4020(76)80111-1

  日期：1976.1