2-(1-hydroxy-cyclohexyl)-propionitrile | 7178-92-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-hydroxy-cyclohexyl)-propionitrile
• 英文别名: 2-(1-Hydroxycyclohexyl)propanenitrile
• CAS: 7178-92-9
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: DUODJECUNIYWQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  2-(1-hydroxy-cyclohexyl)-propionitrile 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 生成 2-(1-羟基环己基)丙酰胺
  参考文献：
  名称：

  Maillard,J. et al., Bulletin de la Societe Chimique de France, 1966, p. 1683 - 1690

  摘要：

  DOI：
• 作为产物：
  描述：

  炔环己醇 生成 2-(1-hydroxy-cyclohexyl)-propionitrile
  参考文献：
  名称：

  FUNARIKI TAKUZO; YAMAZAKI YASUYUKI; TARAMA KIMIO, J. CHEM. SOC. CHEM. COM., 1978, NO 2, 63-65

  摘要：

  DOI：

文献信息

• Hydrocyanation and hydrogenation of acetylenes catalysed by cyanocobaltates
  作者：Takuzo Funabiki、Yasuyuki Yamazaki、Yoshihiro Sato、Satohiro Yoshida

  DOI：10.1039/p29830001915

  日期：——

  [Co(CN)3(bipy)H]–. The preliminary formation of a [π-acetylene–Co(CN)4]3– complex is assumed to explain the fact that the complex is active only at CN : Co < 5 : 1. Hydrocyanation is explained by the reductive coupling of the vinyl and cyano ligands of [σ-vinyl–Co(CN)5]3– which is formed by the reaction of the π-acetylene complex, rather than acetylene itself, with [Co(CN)5H]3–.

  乙炔通过在CN：Co <5：1处制备的氰基钴酸盐进行区域选择性氢氰化，通过不饱和腈通过不使用氰化氢的方法生成饱和仲腈，然后将其部分氢化为烯烃或饱和烃。在2,2'-联吡啶存在下，乙炔的氢化作用占主导地位，反映出高活性氢化物络合物[Co（CN）3（bipy）H] –的形成。假定[π-乙炔-Co（CN）4 ] 3-配合物的初步形成是为了解释该配合物仅在CN：Co <5：1时才有活性。和[σ-乙烯基–Co（CN）5 ] 3–的氰基配体它是由π-乙炔络合物（而不是乙炔本身）与[Co（CN）5 H] 3–反应形成的。
• Iron-Catalysed Reformatsky-Type Reactions
  作者：Muriel Durandetti、Jacques Périchon

  DOI：10.1055/s-2006-926432

  日期：2006.5

  A Reformatsky-type reaction has been developed using iron catalysis in acetonitrile or DMF. Reduction of iron(II) bromide by manganese metal in acetonitrile provides a low-valent iron catalyst, which is the active species; under these conditions, α-chloroesters or nitriles can both be converted into their corresponding derivatives. The method was applicable to both ketones and aldehydes, resulting in the formation of β-hydroxyesters under mild conditions.

  一种 Reformatsky 型反应已采用铁催化体系在乙腈或二甲基甲酰胺中得到开发。通过在乙腈中用锰金属还原二溴化铁，可得到低价铁催化剂，该催化剂为活性物种；在这些条件下，α-氯酯或腈均可转化为相应的衍生物。该方法适用于酮和醛，在温和条件下形成 β-羟基酯。
• 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.
• Metal exchange between an electrogenerated organonickel species and zinc halide: application to an electrochemical, nickel-catalyzed Reformatsky reaction
  作者：Annie Conan、Soline Sibille、Jacques Perichon

  DOI：10.1021/jo00006a012

  日期：1991.3

  The mechanism of the electroreductive coupling of alpha-chloro esters or alpha-chloro nitriles with carbonyl compounds by the means of a sacrificial zinc anode and a nickel catalyst was elucidated by electroanalytical techniques. The mechanism involved reduction of a Ni(II) complex to a Ni(0) complex, oxidative addition of the alpha-chloro ester to the Ni(0) complex, and a Zn(II)/Ni(II) exchange, leading to an organozinc Reformatsky reagent. The electrosynthesis of various beta-hydroxy esters, beta-hydroxy nitriles, and 2,3-epoxy esters was successfully achieved under extremely mild conditions.
• Iron-Mediated Electrochemical Reaction of α-Chloroesters with Carbonyl Compounds
  作者：Muriel Durandetti、Clothilde Meignein、Jacques Périchon

  DOI：10.1021/ol0273046

  日期：2003.2.1

  Reformatsky-type reactions have been performed efficiently using an electroassisted iron-complex catalysis. Valuable product such as beta-hydroxyesters, ketones or nitriles are thus prepared with high yields.