3-((E)-5-methoxy-3-methyl-pent-3-enyl)-2,2-dimethyl-oxirane | 63343-32-8

• 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: 3-((E)-5-methoxy-3-methyl-pent-3-enyl)-2,2-dimethyl-oxirane
• 英文别名: O-methyl-geraniol 6,7-epoxide；3-[(E)-5-methoxy-3-methylpent-3-enyl]-2,2-dimethyloxirane
• CAS: 63343-32-8
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: WAHNNYJHZYNHJH-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-((E)-5-methoxy-3-methyl-pent-3-enyl)-2,2-dimethyl-oxirane 在 lithium perchlorate 作用下， 以 苯 为溶剂， 生成 (E)-8-methoxy-2,6-dimethyl-oct-6-en-3-one
  参考文献：
  名称：

  Platinum hydride addition to geranyl and farnesyl methyl ether

  摘要：

  DOI：

  10.1021/ja00767a028
• 作为产物：
  描述：

  (E)-1-甲氧基-3,7-二甲基-2,6-辛二烯 在 单过氧邻苯二甲酸 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 4.0h， 以60%的产率得到3-((E)-5-methoxy-3-methyl-pent-3-enyl)-2,2-dimethyl-oxirane
  参考文献：
  名称：

  Regioselective epoxidation of allylic alcohols with monoperoxyphthalic acid in water

  摘要：

  The epoxidation of olefinic alcohols in water only has been investigated. Simple allylic alcohols are epoxidized readily and with high yields by m-chloroperoxybenzoic acid. Polyolefinic alcohols are epoxidized regioselectively and with excellent yields by monoperoxyphthalic acid controlling the pH of the medium. The reactions have been carried out in the presence and absence of surfactants, and their role has been investigated.

  DOI：

  10.1021/jo00030a029

文献信息

• Regio-, Diastereo-, and Chemoselectivities in the Dioxirane Oxidation of Acyclic and Cyclic Allylic Alcohols by Methyl(trifluoromethyl)dioxirane (TFD): A Comparison with Dimethyldioxirane
  作者：Waldemar Adam、Rodrigo Paredes、Alexander K. Smerz、L. Angela Valoza

  DOI：10.1002/(sici)1099-0690(199802)1998:2<349::aid-ejoc349>3.0.co;2-r

  日期：1998.2

  regioselectivity of the geraniol epoxidation by methyl(trifluoromethyl)dioxirane (TFD) reveals that as for the less reactive dimethyldioxirane (DMD), hydrogen bonding stabilizes the transition state of the epoxidation. In protic media, the hydrogen bonding is exerted intermolecularly by the solvent, whereas in unpolar, non-hydrogen-bonding solvents intramolecular assistance through the adjacent hydroxy

  甲基（三氟甲基）二环氧乙烷（TFD）对香叶醇环氧化的区域选择性的溶剂依赖性变化表明，对于反应性较低的二甲基二环氧乙烷（DMD），氢键稳定了环氧化的过渡态。在质子介质中，氢键由溶剂在分子间施加，而在非极性，非氢键的溶剂中，通过相邻羟基官能团的分子内辅助起作用，并且有利于对烯丙基醇部分的攻击。对于手性烯丙基醇，另外的空间相互作用在构象固定的过渡态中控制π-面选择性。与DMD相似，TFD环氧化的氢键过渡态中的优选二面角约为130°，此处研究的1和3-5被TFD化学选择性环氧化而未形成相应的烯酮。
• Nali, Micaela; Rindone, Bruno; Tollari, Stefano, Gazzetta Chimica Italiana, 1987, vol. 117, # 4, p. 207 - 212
  作者：Nali, Micaela、Rindone, Bruno、Tollari, Stefano、Valletta, Lorenzo

  DOI：——

  日期：——
• Regioselective epoxidation of allylic alcohols with monoperoxyphthalic acid in water
  作者：Francesco Fringuelli、Raimondo Germani、Ferdinando Pizzo、Fabio Santinelli、Gianfranco Savelli

  DOI：10.1021/jo00030a029

  日期：1992.2

  The epoxidation of olefinic alcohols in water only has been investigated. Simple allylic alcohols are epoxidized readily and with high yields by m-chloroperoxybenzoic acid. Polyolefinic alcohols are epoxidized regioselectively and with excellent yields by monoperoxyphthalic acid controlling the pH of the medium. The reactions have been carried out in the presence and absence of surfactants, and their role has been investigated.
• Platinum hydride addition to geranyl and farnesyl methyl ether
  作者：Martin A. Schwartz、T. Jeffrey Dunn

  DOI：10.1021/ja00767a028

  日期：1972.6