(1RS,2RS,4RS)-1-phenyl-4-tert-butylcyclohexan-1,2-diol | 4127-43-9

• 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,4RS)-1-phenyl-4-tert-butylcyclohexan-1,2-diol
• 英文别名: 1-Phenyl-cis-4-tert.-butyl-cyclohexan-cis-1,2-diol；(1R,2R,4R)-4-tert-butyl-1-phenylcyclohexane-1,2-diol
• CAS: 4127-43-9
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: IRXRAJHRWGDOTL-IIAWOOMASA-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,4RS)-1-phenyl-4-tert-butylcyclohexan-1,2-diol 在 硫酸 、 三氟化硼乙醚 、 magnesium sulfate 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 2.0h， 生成 (4-tert-butyl-2-phenylcyclohexen-1-yl)benzene
  参考文献：
  名称：

  An investigative study of kinetic resolutions by the Sharpless asymmetric dihydroxylation reaction

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)00948-6
• 作为产物：
  描述：

  1-phenyl-cis-4-t-butyl-1,2-epoxycyclohexane 在 氢氧化钾 作用下， 以 乙醇 、 苯 为溶剂， 生成 (1RS,2RS,4RS)-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
• Macchia,B. et al., Gazzetta Chimica Italiana, 1970, vol. 100, p. 35 - 63
  作者：Macchia,B. et al.

  DOI：——

  日期：——
• 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.
• Preparation and stereochemical characterization of the diastereoisomeric 1-phenyl-4-t-butylcyclohexene oxides and 1-phenyl-4-t-butylcyclohexane-1,2-diols
  作者：G. Berti、B. Macchia、F. Macchia

  DOI：10.1016/s0040-4020(01)82481-9

  日期：1968.1

  cis and trans forms of 1-phenyl-4-t-butylcyclohexene oxide were prepared and their conversion into the corresponding glycols was investigated. Several methods, some of which highly stereospecific, were found for the preparation of all four possible diastereoisomeric glycols 5-8, as shown in Chart I. Dimethyl sulphoxide proved to be a good solvent for the diaxial cleavage of epoxides by alkali, while

  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。