(1RS,2RS,4SR)-1-phenyl-4-tert-butylcyclohexan-1,2-diol | 4127-44-0

• 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: (1RS,2RS,4SR)-1-phenyl-4-tert-butylcyclohexan-1,2-diol
• 英文别名: 1-Phenyl-trans-4-tert.-butyl-cyclohexan-cis-1,2-diol；(1R,2R,4S)-4-tert-butyl-1-phenylcyclohexane-1,2-diol
• CAS: 4127-44-0
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: IRXRAJHRWGDOTL-SQWLQELKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1RS,2RS,4SR)-1-phenyl-4-tert-butylcyclohexan-1,2-diol 在 rhodium on alumina 氢气 作用下， 以 水 为溶剂， 生成 (1R,2R,4S)-4-tert-Butyl-bicyclohexyl-1,2-diol
  参考文献：
  名称：

  Macchia,B. et al., Gazzetta Chimica Italiana, 1970, vol. 100, p. 35 - 63

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R,4S,6R)-4-tert-Butyl-1-phenyl-7-oxa-bicyclo[4.1.0]heptane 生成 (1RS,2RS,4SR)-1-phenyl-4-tert-butylcyclohexan-1,2-diol
  参考文献：
  名称：

  非对映异构体1-苯基-4-叔丁基环己烯氧化物和1-苯基-4-叔丁基环己烷-1，2-二醇的制备和立体化学表征

  摘要：

  制备了1-苯基-4-叔丁基环己烯氧化物的顺式和反式，并研究了它们向相应的二醇中的转化。如图I所示，发现了几种方法，其中一些具有高度立体定向性，可用于制备所有四种可能的非对映异构二醇5-8。在酸性条件下的相同溶剂导致diaxial乙二醇7从反式环氧化物3，并以一个diequatorial 8从顺式环氧化物2。从它们的制备方法，反应和NMR谱图推导出所有暴露物和二醇的相对构型。

  DOI：

  10.1016/s0040-4020(01)82481-9

文献信息

• Concerning kinetic resolution by the Sharpless asymmetric dihydroxylation reaction
  作者：Hamish S. Christie、David P. G. Hamon、Kellie L. Tuck

  DOI：10.1039/a906423k

  日期：——

  The transition state for the product-determining step in the Sharpless asymmetric dihydroxlation reaction is not product-like, and effective kinetic resolution can occur when one face of a chiral alkene is hindered.

  在 Sharpless 不对称二羟基化反应中，决定产物步骤的过渡态并不像产物，当手性烯烃的一个面受到阻碍时，就会发生有效的动力学解析。
• Substituent effects on the stereoselectivity of the acid-catalyzed solvolysis of rigid 1-arylcyclohexene oxides. Further evidence for a mechanism implying different benzylic carbocationic species
  作者：Paolo Crotti、Giuliana Dell'Omodarme、Maria Ferretti、Franco Macchia

  DOI：10.1021/ja00239a028

  日期：1987.3
• An investigative study of kinetic resolutions by the Sharpless asymmetric dihydroxylation reaction
  作者：David P.G Hamon、Kellie L Tuck、Hamish S Christie

  DOI：10.1016/s0040-4020(01)00948-6

  日期：2001.11

  The requirements for a highly selective kinetic resolution with the Sharpless asymmetric dihydroxylation (AD) reaction were investigated with a number of alkene substrates. It was found that with 1-phenyl-4-tert-butylcyclohexene enantioselectivity is very high, yet diastereoselectivity is poor and kinetic resolution is ineffective. With 5-methyl-2-phenylbicyclo[3.2.0]heptan-2-ene both diastereoselectivity and enantioselectivity are high and kinetic resolution is effective. It was discovered that the transition state for the product-determining step in the Sharpless AD reaction is not product-like, and effective kinetic resolution can occur when one face of a chiral alkene is hindered. (C) 2001 Elsevier Science Ltd. All rights reserved.