[(2R,3Z,9E,11E)-12-(3,5-dimethoxyphenyl)-2-methyl-5-oxododeca-3,9,11-trienyl] 2,2-dimethylpropanoate | 1234628-07-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(2R,3Z,9E,11E)-12-(3,5-dimethoxyphenyl)-2-methyl-5-oxododeca-3,9,11-trienyl] 2,2-dimethylpropanoate
• CAS: 1234628-07-9
• 化学式: C₂₆H₃₆O₅
• 分子量: 428.569
• InChiKey: OXKFXLPSMXZUJW-JCKQKOLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2R,3Z,9E,11E)-12-(3,5-dimethoxyphenyl)-2-methyl-5-oxododeca-3,9,11-trienyl] 2,2-dimethylpropanoate 在 二甲基氯化铝 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-2-((1S,2S,4aR,8aR)-2-(3,5-dimethoxyphenyl)-8-oxo-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)propyl pivalate 、 (R)-2-(2-(3,5-dimethoxyphenyl)-8-oxo-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)propyl pivalate
  参考文献：
  名称：

  Exploring the Original Proposed Biosynthesis of (+)-Symbioimine: Remote Exocyclic Stereocontrol in a Type I IMDA Reaction

  摘要：

  The originally proposed biosynthesis of (+)-symbioimine was explored, resulting in the successful intramolecular Diels-Alder (IMDA) cyclization of an appropriate (E,E,E)-1,7,9-decatrien-3-one. In contrast to the originally proposed biosynthesis, the IMDA reaction appears to proceed via an endo transition state. Remarkably, a single exocyclic stereogenic center effectively controls the pi-facial selectivity affording a highly diastereoselective cycloaddition.

  DOI：

  10.1021/ol101141a
• 作为产物：
  描述：

  在 吡啶 、 氢气 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以61%的产率得到[(2R,3Z,9E,11E)-12-(3,5-dimethoxyphenyl)-2-methyl-5-oxododeca-3,9,11-trienyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Exploring the Original Proposed Biosynthesis of (+)-Symbioimine: Remote Exocyclic Stereocontrol in a Type I IMDA Reaction

  摘要：

  The originally proposed biosynthesis of (+)-symbioimine was explored, resulting in the successful intramolecular Diels-Alder (IMDA) cyclization of an appropriate (E,E,E)-1,7,9-decatrien-3-one. In contrast to the originally proposed biosynthesis, the IMDA reaction appears to proceed via an endo transition state. Remarkably, a single exocyclic stereogenic center effectively controls the pi-facial selectivity affording a highly diastereoselective cycloaddition.

  DOI：

  10.1021/ol101141a

文献信息

• Exploring the Original Proposed Biosynthesis of (+)-Symbioimine: Remote Exocyclic Stereocontrol in a Type I IMDA Reaction
  作者：Jason P. Burke、Michal Sabat、Diana A. Iovan、William H. Myers、Jason J. Chruma

  DOI：10.1021/ol101141a

  日期：2010.7.16

  The originally proposed biosynthesis of (+)-symbioimine was explored, resulting in the successful intramolecular Diels-Alder (IMDA) cyclization of an appropriate (E,E,E)-1,7,9-decatrien-3-one. In contrast to the originally proposed biosynthesis, the IMDA reaction appears to proceed via an endo transition state. Remarkably, a single exocyclic stereogenic center effectively controls the pi-facial selectivity affording a highly diastereoselective cycloaddition.