ethyl (E)-3-[(3S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-5-[(4-methoxyphenyl)methoxymethyl]-3-methylcyclopenten-1-yl]-2-methylprop-2-enoate | 1114552-87-2

• 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: ethyl (E)-3-[(3S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-5-[(4-methoxyphenyl)methoxymethyl]-3-methylcyclopenten-1-yl]-2-methylprop-2-enoate
• CAS: 1114552-87-2
• 化学式: C₂₇H₄₂O₅Si
• 分子量: 474.713
• InChiKey: ONRBBWSNGXBWSI-MXTWMWEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  三乙基2-膦酰基丙酯 、 [(1R,2S,3R,5S)-3-[tert-butyl(dimethyl)silyl]oxy-2-formyl-3-[(4-methoxyphenyl)methoxymethyl]-5-methylcyclopentyl] benzoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以34%的产率得到ethyl (E)-3-[(3S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-5-[(4-methoxyphenyl)methoxymethyl]-3-methylcyclopenten-1-yl]-2-methylprop-2-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

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.