<1S-(exo,exo)>-4,7,7-Trimethyl-3-(1-naphthyl)bicyclo<2.2.1>heptan-2-yl acetate | 137696-28-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: <1S-(exo,exo)>-4,7,7-Trimethyl-3-(1-naphthyl)bicyclo<2.2.1>heptan-2-yl acetate
• CAS: 137696-28-7
• 化学式: C₂₂H₂₆O₂
• 分子量: 322.447
• InChiKey: NGKZRMYUGYBASG-VMBXEPDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  <1S-(exo,exo)>-4,7,7-Trimethyl-3-(1-naphthyl)bicyclo<2.2.1>heptan-2-yl acetate 在 正丁基锂 、 N-环己基异丙基胺 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 3.92h， 生成 <1S-(exo,exo)>-4,7,7-Trimethyl-3-(1-naphthyl)bicyclo<2.2.1>heptan-2-yl 3(R)-hydroxy-(E,E)-4,6-dodecadienoate
  参考文献：
  名称：

  Enantioselective rhodium-mediated synthesis of (-)-PGE2 methyl ester

  摘要：

  Intramolecular Rh(II) carboxylate catalyzed cyclization of an alpha-diazo beta-methylene ketone to form a fused cyclopropane is shown to compete efficiently with beta-hydride elimination, so long as a catalyst derived from an electron-donating carboxylate is used. Cyclization of diazoketone 3 gives 2, which on opening with thiophenol followed by oxidative rearrangement gives PGE2 methyl ester 1. Prostaglandins having the 8-beta configuration, recently identified as being physiologically important, can also be prepared using this approach.

  DOI：

  10.1021/jo00028a012
• 作为产物：
  描述：

  乙酸酐 、 (4S)-3-exo-(1-naphthyl)-4,7,7-trimethylbicyclo[2.2.1]heptan-2-exo-ol 在 sodium acetate 作用下， 反应 18.0h， 以96%的产率得到<1S-(exo,exo)>-4,7,7-Trimethyl-3-(1-naphthyl)bicyclo<2.2.1>heptan-2-yl acetate
  参考文献：
  名称：

  Enantioselective rhodium-mediated synthesis of (-)-PGE2 methyl ester

  摘要：

  Intramolecular Rh(II) carboxylate catalyzed cyclization of an alpha-diazo beta-methylene ketone to form a fused cyclopropane is shown to compete efficiently with beta-hydride elimination, so long as a catalyst derived from an electron-donating carboxylate is used. Cyclization of diazoketone 3 gives 2, which on opening with thiophenol followed by oxidative rearrangement gives PGE2 methyl ester 1. Prostaglandins having the 8-beta configuration, recently identified as being physiologically important, can also be prepared using this approach.

  DOI：

  10.1021/jo00028a012