(-)-(3-methyl-3-phenyl-oxiranyl)-methanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (-)-(3-methyl-3-phenyl-oxiranyl)-methanol
• 英文别名: (3-Methyl-3-phenyloxiran-2-yl)methanol
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: HVVKBTOOVVNCAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (-)-(3-methyl-3-phenyl-oxiranyl)-methanol 在 碳酸氢钠 、 戴斯-马丁氧化剂 、 甲酰甲撑基三苯基磷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  N-杂环卡宾催化的级联环氧化物开环和内酯化反应合成二氢吡喃酮衍生物†

  摘要：

  N-杂环卡宾被用作有效的有机催化剂，以催化级联的环氧化物开环和内酯化反应。这种有机催化过程可以将各种容易获得的γ-环氧-α，β-烯醛转变为二氢吡喃酮 衍生品，收益率高至优。

  DOI：

  10.1039/c1ob05854a
• 作为产物：
  描述：

  杨梅醛 在 C₃₃H₂₉FeMnN₂O₃P 、 氢气 、 potassium carbonate 作用下， 90.0 ℃ 、5.0 MPa 条件下， 反应 16.0h， 以71%的产率得到(-)-(3-methyl-3-phenyl-oxiranyl)-methanol
  参考文献：
  名称：

  对映体纯酯的锰催化加氢

  摘要：

  锰的酯催化氢化反应已完成，TONs的用量高达1000，分别使用廉价，对环境无害的碳酸钾和简单的醇作为活化剂和溶剂。弱碱性条件导致良好的官能团耐受性，并能够氢化对映异构体富集的α-手性酯，而基本上不损失立体化学完整性。

  DOI：

  10.1021/acs.orglett.8b00864

文献信息

• Amino acid-derived hydroxamic acids as chiral ligands in the vanadium catalysed epoxidation
  作者：Andrei V. Malkov、Zaïnaba Bourhani、Pavel Kočovský

  DOI：10.1039/b505324b

  日期：——

  New sulfonamide-derived hydroxamic acids have been developed as chiral ligands for the V-catalysed asymmetric epoxidation, showing high reactivity at subzero temperatures and moderate to good enantioselectivity. The strong accelerating effect exhibited by the ligands of this type can be attributed to the sulfonamide functionality. A range of cinnamyl type allylic alcohols were epoxidised with up to

  已开发出新的磺酰胺衍生的异羟肟酸作为V催化的不对称环氧化的手性配体，在零度以下温度下显示出高反应活性，对映选择性中等至良好。这种配体表现出的强促进作用可归因于磺酰胺官能团。一系列肉桂基类型的烯丙基醇被高达74％的ee环氧化。
• Enantioselective iminium-catalyzed epoxidation of hindered trisubstituted allylic alcohols
  作者：Roman Novikov、Jérôme Lacour

  DOI：10.1016/j.tetasy.2010.06.002

  日期：2010.6

  The reactivity of diastereomeric biaryl iminium cations made of a (Ra)-5,5',6,6',7,7',8,8'-octahydrobinaphthyl core and exocyclic appendages derived from (S)- or (R)-3,3-dimethylbutyl-2-amine was investigated with hindered trisubstituted allylic alcohols a class of alkenes which had not been previously studied in detail in epoxidation reactions with cyclic iminium catalysts (ee up to 98%). Surprisingly, generally strong matched/mismatched effects are observed not only in terms of reactivity but also on the enantioselectivity of the reaction (Ace up to 16%). Also, for the most hindered substrates, two sets of reaction conditions were tested in a preliminary study and little advantage was found in running reactions in MeCN/water instead of CH(2)Cl(2)/water/18-C-6. In any case, the presence of the hydroxyl group did not reveal any anchimeric effect. (C) 2010 Elsevier Ltd. All rights reserved.
• A CATALYTICAL ASYMMETRIC EPOXIDATION
  申请人：UNIVERSITY OF CHICAGO

  公开号：EP1706205B1

  公开（公告）日：2008-10-29
• Catalytic asymmetric epoxidation
  申请人：Yamamoto Hisashi

  公开号：US20070203347A1

  公开（公告）日：2007-08-30

  The present invention relates to the synthesis of chiral epoxides via a catalytic asymmetric oxidation of olefins. Additionally, the methodology provides a method of asymmetrically oxidizing sulfides and phosphines. This asymmetric oxidation employs a catalyst system composed of a metal and a chiral bishydroxamic acid ligand, which, in the presence of a stoichiometric oxidation reagent, serves to asymmetrically oxidize a variety of substrates.
• US7202371B2
  申请人：——

  公开号：US7202371B2

  公开（公告）日：2007-04-10