(±)-cis-6-methyl-7-oxabicyclo[4.1.0]heptan-2-ol | 38309-43-2

• 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: (±)-cis-6-methyl-7-oxabicyclo[4.1.0]heptan-2-ol
• 英文别名: 3-methyl-trans-2,3-epoxycyclohexan-1-ol；(1R,2S,6S)-6-methyl-7-oxabicyclo[4.1.0]heptan-2-ol
• CAS: 38309-43-2；57456-95-8；112837-24-8；112837-25-9
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: YXTCGMZRVAMAJM-XVMARJQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• 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

• 作为产物：
  描述：

  6-甲基-7-氧杂双环[4.1.0]庚烷-2-酮 在 diisopropoxytitanium(III) tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以93%的产率得到(±)-cis-6-methyl-7-oxabicyclo[4.1.0]heptan-2-ol
  参考文献：
  名称：

  四氢硼酸二异丙氧基钛（III）的化学和立体选择性还原α，β-环氧酮

  摘要：

  在温和的条件下（-78°→-20°C），用四氢硼酸二异丙氧基钛（III）在二氯甲烷中还原α，β-环氧酮可提供高收率的抗-（或赤型）α，β-环氧醇，且具有高度的化学反应性-和立体选择性。

  DOI：

  10.1016/0040-4020(96)00465-6

文献信息

• Oxygen transfer reactions from an Oxaziridinium tetrafluoroborate salt to Olefins
  作者：Xavier Lusinchi、Gilles Hanquet

  DOI：10.1016/s0040-4020(97)00890-9

  日期：1997.10

  Oxaziridinium efficiently epoxidises olefins. It reacts as an electrophilic reagent and does not transfer its oxygen to deactivated double-bonds or carbonyl functions. Epoxidation of cyclic allylic acetates shows a remarkable diastereoselectivity leading to the syn isomer. We propose that the epoxidation reaction proceeds through a one-step process.

  恶嗪鎓有效地环氧化烯烃。它作为亲电子试剂反应，不会将其氧转移到失活的双键或羰基官能团上。环状烯丙基乙酸酯的环氧化显示出显着的非对映选择性，导致了顺式异构体。我们建议环氧化反应通过一个一步的过程进行。
• Stereo- and regioselectivity in the P450-catalyzed oxidative tandem difunctionalization of 1-methylcyclohexene
  作者：Gheorghe-Doru Roiban、Rubén Agudo、Manfred T. Reetz

  DOI：10.1016/j.tet.2013.04.132

  日期：2013.7

  non-functionalized molecules using biocatalysis based on P450 monooxygenases is known to be difficult due to the expected poor regio- and stereoselectivity, but in this study it was nevertheless attempted. 1-Methylcyclohexene was subjected to oxygen-mediated biocatalytic oxidation using P450-BM3 as the catalyst. Both oxidative hydroxylation and epoxidation were observed, in some cases leading to hydroxy epoxides with

  已知由于预期的不良的区域选择性和立体选择性，使用基于P450单加氧酶的生物催化方法难以选择性地将小的未官能化分子进行部分氧化，但是在本研究中仍尝试进行。使用P450-BM3作为催化剂，对1-甲基环己烯进行氧介导的生物催化氧化。观察到氧化性羟基化和环氧化，在某些情况下导致具有高非对映和对映选择性的羟基环氧化物，尤其是当使用BM3突变体时。
• Diastereoselective epoxidation of allylically substituted alkenes using metalloporphyrin catalysts
  申请人：Che Chi-Ming

  公开号：US20050209470A1

  公开（公告）日：2005-09-22

  Diastereoselective epoxidation of allylically substituted alkenes using metalloporphyrins as catalyst provides high trans-selectivities (i.e., trans-:cis-epoxide ratio). A diversity of cycloalkenes bearing different allylic substituents are shown to be efficiently epoxidized to afford the corresponding trans-epoxides with excellent trans-selectivities (up to >98%) and good yields (up to 99%). Acyclic allylic alkenes bearing different allylic substituents are efficiently epoxidized to afford the corresponding erythro-epoxides with good erythro-selectivities. The metalloporphyrin-catalyzed reactions exhibit up to 20 times higher trans-selectivities than the conventional method using m-chloroperoxybenzoic acid as oxidant.

  使用金属卟啉作为催化剂的烯丙基取代烯烃的非对映选择性环氧化反应提供高选择性（即反式：顺式环氧化物比）。显示出带有不同烯丙基取代基的多样环烯烃能够有效地环氧化，产生相应的反式环氧化物，具有优异的反式选择性（高达>98%）和良好的产率（高达99%）。带有不同烯丙基取代基的无环烯丙基烯烃能够有效地环氧化，产生相应的顺式环氧化物，具有良好的顺式选择性。金属卟啉催化的反应显示出比使用m-氯过氧苯甲酸作为氧化剂的传统方法高达20倍的反式选择性。
• Borinic Acid Catalyzed, Regioselective Chloroacylations and Chlorosulfonylations of 2,3-Epoxy Alcohols
  作者：Kashif Tanveer、Kareem Jarrah、Mark S. Taylor

  DOI：10.1021/acs.orglett.5b01541

  日期：2015.7.17

  In the presence of a borinic acid derived catalyst, 2,3-epoxy alcohols undergo couplings with acyl and sulfonyl chlorides. This transformation directly generates O-acylated or O-sulfonylated chlorohydrin diols, with significant levels of regioselectivity for both the ring-opening and O-functionalization steps.
• Mokhtar, Hassan M.; Zaidlewicz, Marek, Polish Journal of Chemistry, 1981, vol. 55, # 4, p. 757 - 761
  作者：Mokhtar, Hassan M.、Zaidlewicz, Marek

  DOI：——

  日期：——