(3E,5R,9E,13S,14R)-5,9,13,14-tetramethyl-5-triethylsilyloxy-1-oxacyclotetradeca-3,9-diene-2,8-dione | 1104198-28-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (3E,5R,9E,13S,14R)-5,9,13,14-tetramethyl-5-triethylsilyloxy-1-oxacyclotetradeca-3,9-diene-2,8-dione
• CAS: 1104198-28-8
• 化学式: C₂₃H₄₀O₄Si
• 分子量: 408.654
• InChiKey: GPMSKJDHBGWBJK-MYHCPMOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3E,5R,9E,13S,14R)-5,9,13,14-tetramethyl-5-triethylsilyloxy-1-oxacyclotetradeca-3,9-diene-2,8-dione 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以80%的产率得到(3E,5R,8R,9E,13S,14R)-8-hydroxy-5,9,13,14-tetramethyl-5-triethylsilyloxy-1-oxacyclotetradeca-3,9-dien-2-one
  参考文献：
  名称：

  Total Synthesis of (−)-5,6-Dihydrocineromycin B

  摘要：

  An asymmetric total synthesis of (-)-5,6-dihydrocineromycin B has been accomplished in 13 steps from (-)-linalool O-triethylsilyl ether or 12 steps from geraniol. The present synthesis features (i) an intermolecular Wittig reaction involving an aldehyde possessing a ketophosphonate functionality and (ii) an intramolecular Horner-Wadsworth-Emmons olefination.

  DOI：

  10.1021/jo802503x
• 作为产物：
  描述：

  [(2R,3S)-3-methyl-6-oxohexan-2-yl] (E,4R)-8-diethoxyphosphoryl-4-methyl-7-oxo-4-triethylsilyloxynon-2-enoate 在 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 乙腈 为溶剂， 以65%的产率得到(3E,5R,9E,13S,14R)-5,9,13,14-tetramethyl-5-triethylsilyloxy-1-oxacyclotetradeca-3,9-diene-2,8-dione
  参考文献：
  名称：

  Total Synthesis of (−)-5,6-Dihydrocineromycin B

  摘要：

  An asymmetric total synthesis of (-)-5,6-dihydrocineromycin B has been accomplished in 13 steps from (-)-linalool O-triethylsilyl ether or 12 steps from geraniol. The present synthesis features (i) an intermolecular Wittig reaction involving an aldehyde possessing a ketophosphonate functionality and (ii) an intramolecular Horner-Wadsworth-Emmons olefination.

  DOI：

  10.1021/jo802503x

文献信息

• Total Synthesis of (−)-5,6-Dihydrocineromycin B
  作者：Guozhi Li、Xiaoxia Yang、Hongbin Zhai

  DOI：10.1021/jo802503x

  日期：2009.2.6

  An asymmetric total synthesis of (-)-5,6-dihydrocineromycin B has been accomplished in 13 steps from (-)-linalool O-triethylsilyl ether or 12 steps from geraniol. The present synthesis features (i) an intermolecular Wittig reaction involving an aldehyde possessing a ketophosphonate functionality and (ii) an intramolecular Horner-Wadsworth-Emmons olefination.