1-(1,2-Epoxycyclohexyl)cyclohexan-1-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 1-(1,2-Epoxycyclohexyl)cyclohexan-1-ol
• 英文别名: 1-[(1R,6S)-7-oxabicyclo[4.1.0]heptan-1-yl]cyclohexan-1-ol
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: SLVRYMGZWQKEHR-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1,2-Epoxycyclohexyl)cyclohexan-1-ol 在 aluminum isopropoxide 作用下， 以 异丙醇 为溶剂， 以60%的产率得到(1R,6S,7S)-Spiro[5.6]dodecane-1,7-diol
  参考文献：
  名称：

  从 α-羟基环氧化物中提取立体定向螺环二醇的面部一步法

  摘要：

  报道了一种用异丙醇铝从 α-羟基环氧化物合成立体定向螺环二醇的新一步法，该方法立体定向、简单且高效。还讨论了一些产品的立体化学归属。

  DOI：

  10.1246/cl.1998.285
• 作为产物：
  描述：

  1-氯环己烯 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 lithium 作用下， 以 乙醚 、 苯 为溶剂， 反应 12.0h， 生成 1-(1,2-Epoxycyclohexyl)cyclohexan-1-ol
  参考文献：
  名称：

  Stereoselective construction of quaternary centers at ambient temperature by the highly stereocontrolled migration of groups containing sp-, sp2-, and sp3-hybridized carbon atoms

  摘要：

  A very highly diastereoselective semipinacol rearrangement of 2,3-epoxy alcohols mediated by tin(IV) chloride at ambient temperatures is shown to be applicable to a wide variety of migrating groups including methyl, tert-butyl, cyclopropyl, vinyl, alkynyl, phenyl, and 2-furyl. A synthetically valuable feature is that a mixture of syn- and anti-epoxy alcohols affords only a single diastereoisomerically pure beta-hydroxy ketone. Additional advantages of the reaction include the presence in the product of two adjacent stereocenters and the efficient creation of a new quaternary center, valuable features in the synthesis of a variety of natural products.

  DOI：

  10.1021/jo00074a019

文献信息

• Zinc bromide as catalyst for the stereoselective construction of quaternary carbon: improved synthesis of diastereomerically enriched spirocyclic diols
  作者：Yong Qiang Tu、Chun An Fan、Shi Kuo Ren、Albert S. C. Chan

  DOI：10.1039/b006182o

  日期：——

  proved to be a facile and efficient catalyst for the stereoselective semipinacol rearrangement of α-hydroxy epoxides at room temperature. Of note are the presence in the product of two adjacent chiral carbon centers, particularly the creation of a stereoselective quaternary center, and the efficient synthesis of β-hydroxy ketones, including some with naturally occurring spiroalkane skeletons. As an

  溴化锌（ZnBr 2）被证明是一种便捷有效的方法催化剂用于室温下α-羟基环氧化物的立体选择性半松果酚重排。值得注意的是在产物中存在两个相邻的手性碳中心，特别是建立了一个立体选择性四元中心，以及高效合成了β-羟基酮类，包括一些具有自然形成的螺烷骨架的物质。作为其应用的一个例子，重要的非对映体富集的螺环二醇 配体通过这种重新排列方便地合成，随后减少 环β-羟基的数量 酮类 适当获得 氢化物 试剂。
• Stereoselective construction of quaternary centers at ambient temperature by the highly stereocontrolled migration of groups containing sp-, sp2-, and sp3-hybridized carbon atoms
  作者：Charles M. Marson、Andrew J. Walker、Jane Pickering、Adrian D. Hobson、Roger Wrigglesworth、Simon J. Edge

  DOI：10.1021/jo00074a019

  日期：1993.10

  A very highly diastereoselective semipinacol rearrangement of 2,3-epoxy alcohols mediated by tin(IV) chloride at ambient temperatures is shown to be applicable to a wide variety of migrating groups including methyl, tert-butyl, cyclopropyl, vinyl, alkynyl, phenyl, and 2-furyl. A synthetically valuable feature is that a mixture of syn- and anti-epoxy alcohols affords only a single diastereoisomerically pure beta-hydroxy ketone. Additional advantages of the reaction include the presence in the product of two adjacent stereocenters and the efficient creation of a new quaternary center, valuable features in the synthesis of a variety of natural products.
• A Facial One-step Approach to Stereospecific Spirocyclic Diols from α-Hydroxyepoxides
  作者：Yong Qiang Tu、Li Ming Yang、Yao Zu Chen

  DOI：10.1246/cl.1998.285

  日期：1998.4

  A new 1-step method for synthesis of stereospecific spirocyclic diols from α-hydroxyepoxids with aluminum isopropoxide was reported, which was stereospecific, simple and highly effective. The stereochemical assignment of some products was also discussed.

  报道了一种用异丙醇铝从 α-羟基环氧化物合成立体定向螺环二醇的新一步法，该方法立体定向、简单且高效。还讨论了一些产品的立体化学归属。