(+/-)-1-hydroxymethyl-cis-2-methylcyclohexanol | 74397-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-1-hydroxymethyl-cis-2-methylcyclohexanol
• 英文别名: cis-1-(Hydroxymethyl)-2-methyl-1-cyclohexanol；(+/-)-1-hydroxymethyl-2c-methyl-cyclohexan-r-ol；(1S,2R)-1-(hydroxymethyl)-2-methylcyclohexan-1-ol
• CAS: 74397-20-9；74397-21-0；101869-70-9；141422-24-4；141422-25-5
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: DJFFQUJMGMVNIW-HTQZYQBOSA-N

物化性质

• 熔点：
  55-58 °C
• 沸点：
  245.8±8.0 °C(Predicted)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 (+/-)-1-hydroxymethyl-cis-2-methylcyclohexanol
  参考文献：
  名称：

  Nasarow; Kamernizkii; Achrem, Zhurnal Obshchei Khimii, 1958, vol. 28, p. 1458,1459

  摘要：

  DOI：

文献信息

• Practical hydroxymethylation of aldehydes and ketones via pinacol cross-coupling reactions with paraformaldehyde
  作者：Jeonghan Park、Steven F. Pedersen

  DOI：10.1016/s0040-4020(01)88875-x

  日期：——

  method for the direct hydroxymethylation of aldehydes and ketones via pinacol cross-coupling with paraformaldehyde is described. The reaction is promoted by vanadium(II) ions which are conveniently generated from the reduction of VCl3(THF)3 with zinc dust. Excellent yields of terminal diols are obtained and stereoselective coupling is observed with some chiral aldehydes and ketones.

  描述了通过频哪醇与多聚甲醛交叉偶联直接醛和酮进行羟甲基化的一般实用方法。钒（II）离子可促进反应，钒离子可通过用锌粉还原VCl 3（THF）3方便地产生。获得了优异的末端二醇收率，并且观察到与一些手性醛和酮的立体选择性偶联。
• Stereoselectivity and Substrate Specificity in the Kinetic Resolution of Methyl-Substituted 1-Oxaspiro[2.5]octanes by <i>Rhodotorula </i><i>g</i><i>lutinis</i> Epoxide Hydrolase
  作者：Carel A. G. M. Weijers、Petra Meeuwse、Robert L. J. M. Herpers、Maurice C. R. Franssen、Ernst J. R. Sudhölter

  DOI：10.1021/jo050533w

  日期：2005.8.1

  [GRAPHICS]The kinetic resolution of a range of methyl-substituted 1-oxaspiro[2.5]octanes by yeast epoxide hydrolase (YEH) from Rhodotorula glutinis has been investigated. The structural determinants of substrate specificity and stereoselectivity of YEH toward these substrates appeared to be the configuration of the epoxide ring and the substitution pattern of the cyclohexane ring. For all compounds tested, O-axial epoxides were hydrolyzed faster than the corresponding O-equatorial compounds. In concern of the ring substituents,.YEH preferred methyl groups on the Re side of the ring. Placement of substituents close to the spiroepoxide carbon decreased the reaction rate but increased enantioselectivity. YEH-catalyzed kinetic resolutions of 4-methyl 1-oxaspiro [2.5] octane epimers were most enantioselective,(E > 100).
• Kinetic resolution by epoxide hydrolase catalyzed hydrolysis of racemic methyl substituted methylenecyclohexene oxides
  作者：Giuseppe Bellucci、Cinzia Chiappe、Giovanni Ingrosso、Carlo Rosini

  DOI：10.1016/0957-4166(95)00250-s

  日期：1995.8

  A complete kinetic resolution of 2,2-dimethylmethylenecyclobexene oxide and a partial resolution of the cis and trans-2-methylmethylenecyclohexene oxides, but not of their 3-methyl substituted isomers, have been achieved by partial hydrolysis to the corresponding diols using the microsomal epoxide hydrolase. No substrate enantioselectivity was in found for the hydrolysis of all these substrates by the cytosolic epoxide hydrolase.