(3S)-4-methyl-3,4-epoxypentan-1-ol | 255709-02-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (3S)-4-methyl-3,4-epoxypentan-1-ol
• 英文别名: 2-(3,3-dimethyloxiran-2-yl)ethanol；2-[(2S)-3,3-dimethyloxiran-2-yl]ethanol
• CAS: 255709-02-5
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: ZPGGKNZDYTVOTP-YFKPBYRVSA-N

物化性质

• 沸点：
  190.4±8.0 °C(Predicted)
• 密度：
  0.986±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• 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：

  乙酸酐 、 (3S)-4-methyl-3,4-epoxypentan-1-ol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (-)-(S)-4-methyl-3,4-epoxypentan-1-ol acetate
  参考文献：
  名称：

  An Asymmetric Dihydroxylation Route to (3R,5E)-2,6-Dimethyl-2,3-epoxyocta-5,7-diene:  The Major Volatile Component from Male Fruit-Spotting Bugs

  摘要：

  DOI：

  10.1021/jo991407t
• 作为产物：
  描述：

  甲基-3-戊烯-1-醇 在 cumen hydroperoxide 、 Zr(Ot-Bu) 、 (+)-L-酒石酸二苄酰胺 作用下， 以 氯苯 为溶剂， 反应 24.0h， 生成 (3S)-4-methyl-3,4-epoxypentan-1-ol
  参考文献：
  名称：

  Catalytic Enantioselective Epoxidation of Homoallylic Alcohols by Chiral Zirconium Complexes

  摘要：

  Catalytic enantioselective epoxidation of homoallylic alcohols using Zr(Ot-Bu)(4) and tartrate ester (or tartramide) has been developed. In the Zr(Ot-Bu)(4)/diisopropyl tartrate-catalyzed epoxidation, the reverse of the enantiofacial preference was observed, depending on the Zr/ligand ratios of 1:1 or 1:2.

  DOI：

  10.1021/ol027261t

文献信息

• Zirconium(IV)- and Hafnium(IV)-Catalyzed Highly Enantioselective Epoxidation of Homoallylic and Bishomoallylic Alcohols
  作者：Zhi Li、Hisashi Yamamoto

  DOI：10.1021/ja100951u

  日期：2010.6.16

  enantioselective epoxidation of homoallylic alcohols and bishomoallylic alcohols, which used to be quite difficult substrates for other types of asymmetric epoxidation reactions. The performance of the catalyst was improved by adding polar additive and molecular sieves. For homoallylic alcohols, the reaction could provide epoxy alcohols in up to 83% yield and up to 98% ee, while, for bishomoallylic alcohols, up

  在这份报告中，锆 (IV)- 和铪 (IV)-双异羟肟酸配合物用于高对映选择性环氧化的高烯丙醇和双烯丙醇，这曾经是其他类型的不对称环氧化反应非常困难的底物。通过加入极性添加剂和分子筛提高了催化剂的性能。对于高烯丙醇，该反应可以提供高达 83% 的收率和高达 98% 的 ee，而对于双烯丙醇，可以得到高达 79% 的收率和 99% ee 的环氧醇，而不是环化四氢呋喃化合物在大多数情况下。
• Design of a New Bimetallic Catalyst for Asymmetric Epoxidation and Sulfoxidation
  作者：Sukalyan Bhadra、Matsujiro Akakura、Hisashi Yamamoto

  DOI：10.1021/jacs.5b11429

  日期：2015.12.23

  A new chiral tethered 8-quinolinol-based ligand class is developed. The binuclear titanium complex of the ligand operates through a novel mechanism allowing for the regio- and stereoselective epoxidation of primary and tertiary homoallylic alcohols (up to 98% ee), as well as first examples of 2-allylic phenols (up to 92% ee). The new catalyst system also promotes the asymmetric oxidation of gamma-hydroxypropyl sulfides giving an important class of chiral sulfoxides that have been inaccessible to date (up to 95% ee).
• Catalytic Enantioselective Epoxidation of Homoallylic Alcohols by Chiral Zirconium Complexes
  作者：Takahiro Okachi、Norio Murai、Makoto Onaka

  DOI：10.1021/ol027261t

  日期：2003.1.1

  Catalytic enantioselective epoxidation of homoallylic alcohols using Zr(Ot-Bu)(4) and tartrate ester (or tartramide) has been developed. In the Zr(Ot-Bu)(4)/diisopropyl tartrate-catalyzed epoxidation, the reverse of the enantiofacial preference was observed, depending on the Zr/ligand ratios of 1:1 or 1:2.
• An Asymmetric Dihydroxylation Route to (3<i>R</i>,5<i>E</i>)-2,6-Dimethyl-2,3-epoxyocta-5,7-diene:  The Major Volatile Component from Male Fruit-Spotting Bugs
  作者：Christopher J. Moore、Sven Possner、Patricia Hayes、Gregory C. Paddon-Jones、William Kitching

  DOI：10.1021/jo991407t

  日期：1999.12.1