methyl (2E,4S,5S,6E)-2,5-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methylocta-2,6-dienoate | 1114552-60-1

• 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: methyl (2E,4S,5S,6E)-2,5-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methylocta-2,6-dienoate
• CAS: 1114552-60-1
• 化学式: C₂₂H₄₄O₄Si₂
• 分子量: 428.76
• InChiKey: OMWPGTDSLXDGDR-RSBIPHQBSA-N

物化性质

• 沸点：
  423.2±45.0 °C(predicted)
• 密度：
  0.917±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  methyl (2E,4S,5S,6E)-2,5-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methylocta-2,6-dienoate 在 cesium fluoride 作用下， 以 甲醇 为溶剂， 以92%的产率得到methyl (E,4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-4-methyl-2-oxooct-6-enoate
  参考文献：
  名称：

  Synthetic Studies toward Jatrophane Diterpenes from Euphorbia characias. Enantioselective Synthesis of (−)-15-O-Acetyl-3-O-propionyl-17-norcharaciol

  摘要：

  The enantioselective synthesis of (+)-17-norcharaciol is described. An uncatalyzed intramolecular carbonyl-ene reaction and a ring-closing metathesis were used as key C/C-connecting transformations to assemble the trans-bicyclo[10.3.0]pentadecane norditerpenoid core. We also report the evolution of our synthetic strategy toward the fully substituted characiol skeleton and the experiences from this venture.

  DOI：

  10.1021/jo802581g
• 作为产物：
  描述：

  methyl 2-(tert-butyldimethylsiloxy)-2-(dimethoxyphosphoryl)acetate 、 (E,2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-methylhex-4-enal 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.75h， 生成 、 methyl (2E,4S,5S,6E)-2,5-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methylocta-2,6-dienoate
  参考文献：
  名称：

  Synthetic Studies toward Jatrophane Diterpenes from Euphorbia characias. Enantioselective Synthesis of (−)-15-O-Acetyl-3-O-propionyl-17-norcharaciol

  摘要：

  The enantioselective synthesis of (+)-17-norcharaciol is described. An uncatalyzed intramolecular carbonyl-ene reaction and a ring-closing metathesis were used as key C/C-connecting transformations to assemble the trans-bicyclo[10.3.0]pentadecane norditerpenoid core. We also report the evolution of our synthetic strategy toward the fully substituted characiol skeleton and the experiences from this venture.

  DOI：

  10.1021/jo802581g

文献信息

• Synthetic Studies toward Jatrophane Diterpenes from <i>Euphorbia characias</i>. Enantioselective Synthesis of (−)-15-<i>O</i>-Acetyl-3-<i>O</i>-propionyl-17-norcharaciol
  作者：Hannes Helmboldt、Martin Hiersemann

  DOI：10.1021/jo802581g

  日期：2009.2.20

  The enantioselective synthesis of (+)-17-norcharaciol is described. An uncatalyzed intramolecular carbonyl-ene reaction and a ring-closing metathesis were used as key C/C-connecting transformations to assemble the trans-bicyclo[10.3.0]pentadecane norditerpenoid core. We also report the evolution of our synthetic strategy toward the fully substituted characiol skeleton and the experiences from this venture.