methyl (7-oxabicyclo<4.1.0>hept-2-ylidene)ethanoate | 118355-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: methyl (7-oxabicyclo<4.1.0>hept-2-ylidene)ethanoate
• 英文别名: methyl 2,3-epoxycyclohexylidene acetate；methyl 2-(7-oxabicyclo[4.1.0]heptan-2-ylidene)acetate
• CAS: 118355-43-4
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: RXTFGZMLWCHJQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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 (7-oxabicyclo<4.1.0>hept-2-ylidene)ethanoate 在 magnesium 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到3-(carbomethoxymethyl)-2-cyclohexen-1-ol
  参考文献：
  名称：

  Reductive cleavage reaction of .gamma.-functionalized .alpha.,.beta.-unsaturated esters and halomethyls mediated with magnesium in methanol

  摘要：

  Reductive cleavage of various types of C-O and C-N bonds tethered to alpha,beta-unsaturated esters and halomethyls was mediated with magnesium in methanol, which provided a facile method for the synthesis of delta-hydroxy or delta-amino beta,gamma-unsaturated esters and allylic alcohols. Regardless of the geometry (E or Z) of the alpha,beta-unsaturated esters, 1a-b, 5a-c, 11, 13, and 23, the cleavage product obtained was exclusively the E isomer of the corresponding deconjugated hydroxy and amino esters. The steric bias and ring strain of 15, 17, and 21 gave rise to a product mixture of E and Z isomers.

  DOI：

  10.1021/jo00058a038

文献信息

• Neutral alkylations via palladium(0) catalysis
  作者：Barry M. Trost、Gary A. Molander

  DOI：10.1021/ja00409a082

  日期：1981.9
• Method for isomerization a glycidate derivative
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP0153692B1

  公开（公告）日：1992-07-29
• US4621150A
  申请人：——

  公开号：US4621150A

  公开（公告）日：1986-11-04
• Reductive cleavage reaction of .gamma.-functionalized .alpha.,.beta.-unsaturated esters and halomethyls mediated with magnesium in methanol
  作者：Chwang Siek Pak、Eun Lee、Ge Hyeong Lee

  DOI：10.1021/jo00058a038

  日期：1993.3

  Reductive cleavage of various types of C-O and C-N bonds tethered to alpha,beta-unsaturated esters and halomethyls was mediated with magnesium in methanol, which provided a facile method for the synthesis of delta-hydroxy or delta-amino beta,gamma-unsaturated esters and allylic alcohols. Regardless of the geometry (E or Z) of the alpha,beta-unsaturated esters, 1a-b, 5a-c, 11, 13, and 23, the cleavage product obtained was exclusively the E isomer of the corresponding deconjugated hydroxy and amino esters. The steric bias and ring strain of 15, 17, and 21 gave rise to a product mixture of E and Z isomers.