tert-butyl ((3Z,9E,11E)-12-(3,5-dimethoxyphenyl)-2-methyl-5-oxododeca-3,9,11-trien-1-yl)carbamate | 1234627-95-2

• 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: tert-butyl ((3Z,9E,11E)-12-(3,5-dimethoxyphenyl)-2-methyl-5-oxododeca-3,9,11-trien-1-yl)carbamate
• CAS: 1234627-95-2
• 化学式: C₂₆H₃₇NO₅
• 分子量: 443.583
• InChiKey: ZQMPZLMGKBLMTA-VOLNBTOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  32.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((3Z,9E,11E)-12-(3,5-dimethoxyphenyl)-2-methyl-5-oxododeca-3,9,11-trien-1-yl)carbamate 在 二甲基氯化铝 作用下， 生成 tert-butyl (3RS,3aSR,3a(1)RS,4SR,6aRS,9aSR)-4-(3,5-dimethoxyphenyl)-9a-hydroxy-3-methyl-2,3,3a,3a(1),4,6a,7,8,9,9a-decahydro-1H-benzo[de]quinoline-1-carboxylate
  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：

  dimethyl (6E,8E)-9-(3,5-dimethoxyphenyl)-2-oxonona-6,8-dienylphosphonate 、 tert-butyl (2-methyl-3-oxopropyl)carbamate 在 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 16.5h， 以94%的产率得到tert-butyl (3E,9E,11E)-12-(3,5-dimethoxyphenyl)-2-methyl-5-oxododeca-3,9,11-trienylcarbamate
  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