(R,R)-2-[trans-2-(1-methoxy-1-methylethyl)vinyl]-3-methyloxirane

• 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: (R,R)-2-[trans-2-(1-methoxy-1-methylethyl)vinyl]-3-methyloxirane
• 英文别名: (2R,3R)-2-[(E)-3-methoxy-3-methylbut-1-enyl]-3-methyloxirane
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: ZKBWBJTUYLYANA-ZZTMBZGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E,E)-2-methyl-3,5-heptadien-2-ol 在 fructose-derived chiral ketone Sodium tetraborate decahydrate 、 Oxone 、 sodium hydride 、 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 11.5h， 生成 (R,R)-2-[trans-2-(1-methoxy-1-methylethyl)vinyl]-3-methyloxirane
  参考文献：
  名称：

  Highly Regio- and Enantioselective Monoepoxidation of Conjugated Dienes

  摘要：

  This paper describes a highly effective and mild asymmetric monoepoxidation method for conjugated dienes using a fructose-derived chiral ketone 1 as catalyst and Oxone as oxidant. The regioselectivies and enantioslectivies are very high in most cases. For unsymmetrical dienes, the regioselectivity can be regulated by using steric and electronic control. The olefin substrates include trans-disubstituted and trisubstituted olefins that can bear a wide range of functional groups such as hydroxyl groups, TBS ethers, or esters. The enantiomeric excesses for the major monoepoxides range from 89% to 97%. The epoxidation is believed to proceed via a spiro mode.

  DOI：

  10.1021/jo9721195

文献信息

• Highly Regio- and Enantioselective Monoepoxidation of Conjugated Dienes
  作者：Michael Frohn、Molly Dalkiewicz、Yong Tu、Zhi-Xian Wang、Yian Shi

  DOI：10.1021/jo9721195

  日期：1998.5.1

  This paper describes a highly effective and mild asymmetric monoepoxidation method for conjugated dienes using a fructose-derived chiral ketone 1 as catalyst and Oxone as oxidant. The regioselectivies and enantioslectivies are very high in most cases. For unsymmetrical dienes, the regioselectivity can be regulated by using steric and electronic control. The olefin substrates include trans-disubstituted and trisubstituted olefins that can bear a wide range of functional groups such as hydroxyl groups, TBS ethers, or esters. The enantiomeric excesses for the major monoepoxides range from 89% to 97%. The epoxidation is believed to proceed via a spiro mode.