methyl 2-[(3aS,4E,5S,6aR)-4-(bromomethylidene)-2,2-dimethyl-3a,5,6,6a-tetrahydrocyclopenta[d][1,3]dioxol-5-yl]acetate | 1380516-72-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-[(3aS,4E,5S,6aR)-4-(bromomethylidene)-2,2-dimethyl-3a,5,6,6a-tetrahydrocyclopenta[d][1,3]dioxol-5-yl]acetate
• CAS: 1380516-72-2
• 化学式: C₁₂H₁₇BrO₄
• 分子量: 305.169
• InChiKey: QCFJCNUHXSPRHL-WLCSQKTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 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 2-[(3aS,4E,5S,6aR)-4-(bromomethylidene)-2,2-dimethyl-3a,5,6,6a-tetrahydrocyclopenta[d][1,3]dioxol-5-yl]acetate 、 methylzinc chloride 在 palladium diacetate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以51%的产率得到[(3aS,5S,6aR)-4-Eth-(E)-ylidene-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl]-acetic acid methyl ester
  参考文献：
  名称：

  Formal synthesis of (−)-oleocanthal by means of a SmI2-promoted intramolecular coupling of bromoalkyne with α,β-unsaturated ester

  摘要：

  A novel approach to the synthesis of (-)-oleocanthal starting from D-ribose, in which a SmI2-promoted intramolecular coupling of bromoalkyne with alpha,beta-unsaturated ester is a key step, has been developed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.085
• 作为产物：
  描述：

  在 N-溴代丁二酰亚胺(NBS) 、 samarium diiodide 、 六氟异丙醇 、 silver nitrate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 丙酮 为溶剂， 生成 methyl 2-[(3aS,4E,5S,6aR)-4-(bromomethylidene)-2,2-dimethyl-3a,5,6,6a-tetrahydrocyclopenta[d][1,3]dioxol-5-yl]acetate 、 methyl 2-((3aS,5R,6aR,E)-4-(bromomethylene)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-5-yl)acetate
  参考文献：
  名称：

  Formal synthesis of (−)-oleocanthal by means of a SmI2-promoted intramolecular coupling of bromoalkyne with α,β-unsaturated ester

  摘要：

  A novel approach to the synthesis of (-)-oleocanthal starting from D-ribose, in which a SmI2-promoted intramolecular coupling of bromoalkyne with alpha,beta-unsaturated ester is a key step, has been developed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.085