[(1R,4S,5R,6R)-5,6-Bis-acetoxymethyl-3-oxo-bicyclo[2.2.1]hept-(2Z)-ylidene]-acetic acid methyl ester | 201736-11-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: [(1R,4S,5R,6R)-5,6-Bis-acetoxymethyl-3-oxo-bicyclo[2.2.1]hept-(2Z)-ylidene]-acetic acid methyl ester
• 英文别名: methyl (2Z)-2-[(1R,4S,5R,6R)-5,6-bis(acetyloxymethyl)-3-oxo-2-bicyclo[2.2.1]heptanylidene]acetate
• CAS: 201736-11-0
• 化学式: C₁₆H₂₀O₇
• 分子量: 324.331
• InChiKey: WXTGQAZKJVWIFM-RVAUTTTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(1R,4S,5R,6R)-5,6-Bis-acetoxymethyl-3-oxo-bicyclo[2.2.1]hept-(2Z)-ylidene]-acetic acid methyl ester 生成 [(1S,4R,5R,6R)-5,6-Bis-acetoxymethyl-3-oxo-bicyclo[2.2.1]hept-(2E)-ylidene]-acetic acid methyl ester
  参考文献：
  名称：

  Formation of non-racemic E- and Z-olefins based on discrimination of enantiotopic carbonyl groups in α-diketones by a chiral phosphonate reagent

  摘要：

  A chiral HWE reagent reacted with an alternative carbonyl group of meso-alpha-diketones of bicyclo[2.2.1] system to give non-racemic (Z)- and (E)-olefins, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10328-8
• 作为产物：
  描述：

  (4-Oxo-3,5-dioxa-4λ⁵-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-acetic acid methyl ester 、 Acetic acid (1S,2R,3S,4R)-3-acetoxymethyl-5,6-dioxo-bicyclo[2.2.1]hept-2-ylmethyl ester 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以23%的产率得到[(1S,4R,5S,6S)-5,6-Bis-acetoxymethyl-3-oxo-bicyclo[2.2.1]hept-(2E)-ylidene]-acetic acid methyl ester
  参考文献：
  名称：

  Formation of non-racemic E- and Z-olefins based on discrimination of enantiotopic carbonyl groups in α-diketones by a chiral phosphonate reagent

  摘要：

  A chiral HWE reagent reacted with an alternative carbonyl group of meso-alpha-diketones of bicyclo[2.2.1] system to give non-racemic (Z)- and (E)-olefins, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10328-8