methyl cis-2,3-epoxyhexanoate

• 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: methyl cis-2,3-epoxyhexanoate
• 英文别名: Methyl (2R,3R)-3-propyloxirane-2-carboxylate
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: JPMVTOZOWGPQDC-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl cis-2,3-epoxyhexanoate 在 sodium azide 、 magnesium(II) perchlorate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以90%的产率得到methyl syn-3-azido-2-hydroxyhexanoate
  参考文献：
  名称：

  Regiochemical control of the ring opening of 1,2-Epoxides by means of chelating processes. 11. Ring opening reactions of aliphatic mono- and difunctionalized cis and trans 2,3- and 3,4-Epoxy Esters

  摘要：

  The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted by metal ions, was verified in the azidolysis of simple aliphatic cis and trans 2,3- and 3,4-epoxy esters and in the corresponding derivatives bearing an ether functionality (OBn) in an allylic relationship to the oxirane ring. The results indicate that the behavior of these epoxides is influenced both by the opening conditions (standard or metal-assisted) and the promoting metal salt [LiClO4 or Mg(ClO4)(2)].

  DOI：

  10.1016/0040-4020(95)00877-b
• 作为产物：
  描述：

  2-己烯酸甲酯 在 间氯过氧苯甲酸 作用下， 生成 methyl cis-2,3-epoxyhexanoate
  参考文献：
  名称：

  Selective C-2 opening of 2,3-epoxyesters with HN3-amine system: A viable route to β-hydroxy-α-amino acids

  摘要：

  The combination of hydrogen azide with amines has proven to effect the C-2 opening of 2,3-epoxyester with high regioselectivity uniformly for trans-epoxyesters and depending on their structures for cis-2,3-epoxyesters.

  DOI：

  10.1016/s0040-4039(00)74855-6

文献信息

• Regiochemical control of the ring opening of 1,2-Epoxides by means of chelating processes. 11. Ring opening reactions of aliphatic mono- and difunctionalized cis and trans 2,3- and 3,4-Epoxy Esters
  作者：Francesca Azzena、Paolo Crotti、Lucilla Favero、Mauro Pineschi

  DOI：10.1016/0040-4020(95)00877-b

  日期：1995.11

  The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted by metal ions, was verified in the azidolysis of simple aliphatic cis and trans 2,3- and 3,4-epoxy esters and in the corresponding derivatives bearing an ether functionality (OBn) in an allylic relationship to the oxirane ring. The results indicate that the behavior of these epoxides is influenced both by the opening conditions (standard or metal-assisted) and the promoting metal salt [LiClO4 or Mg(ClO4)(2)].
• Selective C-2 opening of 2,3-epoxyesters with HN3-amine system: A viable route to β-hydroxy-α-amino acids
  作者：Seiki Saito、Nobuyosi Takahashi、Teruhiko Ishikawa、Toshio Moriwake

  DOI：10.1016/s0040-4039(00)74855-6

  日期：1991.1

  The combination of hydrogen azide with amines has proven to effect the C-2 opening of 2,3-epoxyester with high regioselectivity uniformly for trans-epoxyesters and depending on their structures for cis-2,3-epoxyesters.