(2R,3Z,9E,11E)-1-[tert-butyl(diphenyl)silyl]oxy-12-(3,5-dimethoxyphenyl)-2-methyldodeca-3,9,11-trien-5-one | 1234627-96-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3Z,9E,11E)-1-[tert-butyl(diphenyl)silyl]oxy-12-(3,5-dimethoxyphenyl)-2-methyldodeca-3,9,11-trien-5-one
• CAS: 1234627-96-3
• 化学式: C₃₇H₄₆O₄Si
• 分子量: 582.855
• InChiKey: NCATXQYKHXAEQF-YMKUOXRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.78
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3Z,9E,11E)-1-[tert-butyl(diphenyl)silyl]oxy-12-(3,5-dimethoxyphenyl)-2-methyldodeca-3,9,11-trien-5-one 在 二甲基氯化铝 作用下， 以 二氯甲烷 为溶剂， 以20 mg的产率得到(4aR,7S,8S,8aR)-8-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-7-(3,5-dimethoxyphenyl)-2,3,4,4a,8,8a-hexahydronaphthalen-1(7H)-one
  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：

  (R,9E,11E)-1-((tert-butyldiphenylsilyl)oxy)-12-(3,5-dimethoxyphenyl)-2-methyldodeca-9,11-dien-3-yn-5-one 在 吡啶 、 氢气 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以40%的产率得到(2R,3Z,9E,11E)-1-[tert-butyl(diphenyl)silyl]oxy-12-(3,5-dimethoxyphenyl)-2-methyldodeca-3,9,11-trien-5-one
  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.