hexahydro-(6S)-isopropenyl-1(3H)-isobenzofuranone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: hexahydro-(6S)-isopropenyl-1(3H)-isobenzofuranone
• 英文别名: (3aS,6S,7aR)-6-prop-1-en-2-yl-3a,4,5,6,7,7a-hexahydro-3H-2-benzofuran-1-one
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: RBZYULMGBSNEBG-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  一氧化碳 、 (S)-(-)-紫苏醇 在 palladium diacetate 、 氢气 、 1,4-双(二苯基膦)丁烷 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以56%的产率得到hexahydro-(6S)-isopropenyl-1(3H)-isobenzofuranone
  参考文献：
  名称：

  The First Stereoselective Palladium-Catalyzed Cyclocarbonylation of β,γ-Substituted Allylic Alcohols

  摘要：

  beta,gamma-Substituted allylic alcohols react with CO in the presence of catalytic quantities of palladium acetate and 1,4-bis(diphenylphosphino)butane affording alpha,beta-substituted-gamma-butyrolactones in 42-85% isolated yields. The complete stereoselectivity observed in some cases is a significant feature of the lactonization reaction, with (E)-allylic alcohols affording trans-disubstituted lactones. Depending on the structure of the allylic alcohol used in the cyclocarbonylation reaction, the formation of the corresponding alkene or the beta,gamma-unsaturated carboxylic acid was observed as a side or the principal reaction.

  DOI：

  10.1021/jo9702709

文献信息

• The First Stereoselective Palladium-Catalyzed Cyclocarbonylation of β,γ-Substituted Allylic Alcohols
  作者：Melanie Brunner、Howard Alper

  DOI：10.1021/jo9702709

  日期：1997.10.1

  beta,gamma-Substituted allylic alcohols react with CO in the presence of catalytic quantities of palladium acetate and 1,4-bis(diphenylphosphino)butane affording alpha,beta-substituted-gamma-butyrolactones in 42-85% isolated yields. The complete stereoselectivity observed in some cases is a significant feature of the lactonization reaction, with (E)-allylic alcohols affording trans-disubstituted lactones. Depending on the structure of the allylic alcohol used in the cyclocarbonylation reaction, the formation of the corresponding alkene or the beta,gamma-unsaturated carboxylic acid was observed as a side or the principal reaction.