(R)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)-3-((S)-hydroxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)but-3-en-2-yl benzoate | 1265883-43-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)-3-((S)-hydroxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)but-3-en-2-yl benzoate
• 英文别名: [(2R)-1-[(1S,3R)-2,2-dimethyl-3-[(E)-2-methyl-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]cyclopropyl]-3-[(S)-hydroxy-[(7S)-7-methyl-1,4-dioxaspiro[4.4]non-8-en-9-yl]methyl]but-3-en-2-yl] benzoate
• CAS: 1265883-43-9
• 化学式: C₃₃H₄₄O₇
• 分子量: 552.708
• InChiKey: DNBJTAYVDAXRNO-DQFJYYDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)-3-((S)-hydroxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)but-3-en-2-yl benzoate 在 吡啶 、 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Total Synthesis of Lathyranoic Acid A

  摘要：

  The first total synthesis of lathyranoic acid A (1) was accomplished stereoselectively in a linear sequence of 20 steps and an overall yield of 1.4%. This modular synthesis featured a cyclic, stereocontrolled Cu-catalyzed intramolecular cyclopropanation to construct the cis-cyclopropane unit, a Grubbs metathesis to construct the gamma-substituted cyclopentenone moiety, and an anion-mediated conjugate addition.

  DOI：

  10.1021/jo102033h
• 作为产物：
  描述：

  (S)-2-bromo-4-methylcyclopent-2-enone 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 11.5h， 生成 (R)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)-3-((S)-hydroxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)but-3-en-2-yl benzoate 、 (R)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)-3-((R)-hydroxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)but-3-en-2-yl benzoate
  参考文献：
  名称：

  Total Synthesis of Lathyranoic Acid A

  摘要：

  The first total synthesis of lathyranoic acid A (1) was accomplished stereoselectively in a linear sequence of 20 steps and an overall yield of 1.4%. This modular synthesis featured a cyclic, stereocontrolled Cu-catalyzed intramolecular cyclopropanation to construct the cis-cyclopropane unit, a Grubbs metathesis to construct the gamma-substituted cyclopentenone moiety, and an anion-mediated conjugate addition.

  DOI：

  10.1021/jo102033h

文献信息

• Total Synthesis of Lathyranoic Acid A
  作者：Li-Fang Yu、Hai-Ning Hu、Fa-Jun Nan

  DOI：10.1021/jo102033h

  日期：2011.3.4

  The first total synthesis of lathyranoic acid A (1) was accomplished stereoselectively in a linear sequence of 20 steps and an overall yield of 1.4%. This modular synthesis featured a cyclic, stereocontrolled Cu-catalyzed intramolecular cyclopropanation to construct the cis-cyclopropane unit, a Grubbs metathesis to construct the gamma-substituted cyclopentenone moiety, and an anion-mediated conjugate addition.