2,3-epoxy-1-(methoxymethoxy)nerol

• 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: 2,3-epoxy-1-(methoxymethoxy)nerol
• 英文别名: (2S,3R)-3-(methoxymethoxymethyl)-2-methyl-2-(4-methylpent-3-enyl)oxirane
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: FMIGTTWJYDDCPM-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-epoxy-1-(methoxymethoxy)nerol 在 potassium tert-butylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以81%的产率得到(E)-3,7-dimethyl-1-(methoxymethoxy)-1,6-octadien-3-ol
  参考文献：
  名称：

  Heteroatom-Assisted Isomerization of Oxiranes to Allylic Alcohols Promoted by Bases

  摘要：

  The isomerization of alkoxy-substituted oxiranes to hydroxy-substituted ene ethers promoted by mixed metal bases has been investigated. The structure of the oxirane substrate (the number, the position, and the type of alkyl substituents on the ring) plays an important role in driving the stereoselectivity of the reaction. Disubstituted oxiranes show a predictable preference for the E-ene ether while trisubstituted substrates give either a mixture of stereoisomers or the E-ene ether exclusively, depending on the location of the third alkyl substituent.

  DOI：

  10.1021/jo00096a020
• 作为产物：
  描述：

  橙花醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 15.0h， 生成 2,3-epoxy-1-(methoxymethoxy)nerol
  参考文献：
  名称：

  Heteroatom-Assisted Isomerization of Oxiranes to Allylic Alcohols Promoted by Bases

  摘要：

  The isomerization of alkoxy-substituted oxiranes to hydroxy-substituted ene ethers promoted by mixed metal bases has been investigated. The structure of the oxirane substrate (the number, the position, and the type of alkyl substituents on the ring) plays an important role in driving the stereoselectivity of the reaction. Disubstituted oxiranes show a predictable preference for the E-ene ether while trisubstituted substrates give either a mixture of stereoisomers or the E-ene ether exclusively, depending on the location of the third alkyl substituent.

  DOI：

  10.1021/jo00096a020

文献信息

• Heteroatom-Assisted Isomerization of Oxiranes to Allylic Alcohols Promoted by Bases
  作者：Alessandro Mordini、Sabina Pecchi、Giuseppe Capozzi、Antonella Capperucci、Alessandro Degl'Innocenti、Gianna Reginato、Alfredo Ricci

  DOI：10.1021/jo00096a020

  日期：1994.8

  The isomerization of alkoxy-substituted oxiranes to hydroxy-substituted ene ethers promoted by mixed metal bases has been investigated. The structure of the oxirane substrate (the number, the position, and the type of alkyl substituents on the ring) plays an important role in driving the stereoselectivity of the reaction. Disubstituted oxiranes show a predictable preference for the E-ene ether while trisubstituted substrates give either a mixture of stereoisomers or the E-ene ether exclusively, depending on the location of the third alkyl substituent.