(1R,2S,4R,6S,7R)-(+)-3-oxotricyclo<2,2,1,0^2,6>heptane-7-carboxylic acid | 50703-32-7

• 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: (1R,2S,4R,6S,7R)-(+)-3-oxotricyclo<2,2,1,0^2,6>heptane-7-carboxylic acid
• 英文别名: (1S,2R,4S,6R,7S)-(-)-3-oxotricyclo<2,2,1,0^2,6>heptane-7-carboxylic acid；Norticyclan-3-on-anti-5-carbonsaeure；(1S,2R,3R,4R,6S)-5-Oxotricyclo[2.2.1.02,6]heptane-3-carboxylic acid
• CAS: 50703-32-7；51095-84-2；52730-40-2；70748-53-7；71155-07-2；79356-38-0；128777-69-5
• 化学式: C₈H₈O₃
• 分子量: 152.15
• InChiKey: YUOZAHBGIJALKD-KGJVWPDLSA-N

物化性质

• 沸点：
  356.4±25.0 °C(Predicted)
• 密度：
  1.601±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  (1R,2S,4R,6S,7R)-(+)-3-oxotricyclo<2,2,1,0^2,6>heptane-7-carboxylic acid 在 4-二甲氨基吡啶 、 sodium hydroxide 、 phosphate buffer 、 葡萄糖 、 Kluyveromyces marxianus CBS 2235 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 23.0h， 生成 (+)-anti-5-oxotricyclo<2.2.1.0^2,6>heptane-3-carboxylic acid
  参考文献：
  名称：

  A new chemoenzymatic synthesis of d-cloprostenol

  摘要：

  A new chemoenzymatic synthesis Of D-cloprostenol based on the biocatalytical resolution of anti-2-oxotricyclo[2.2.1.0]heptan-7-carboxylic acid 1 has been developed. The resolution was attempted by different approaches: esterification or reduction of the acid and hydrolysis or reduction of the corresponding esters. The most efficient method proved to be the reduction of the propyl esters of 1 catalysed by the yeast Kluyveromyces marxianus, which allowed for the recovery of the enantiomerically pure ester of anti-2-oxotricyclo[2.2.1.0]heptan-(R)-7-carboxylic acid (R)-3 at 60% molar conversion of 3.0 g/l of racemic substrate acid under optimised conditions. anti-2-Oxotricyclo[2.2. 1.0]heptan-(R)-7-carboxylic acid was obtained by alkaline hydrolysis and employed for the synthesis of D-cloprostenol. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.08.038
• 作为产物：
  描述：

  5-氧代-三环[2.2.1.02,6]庚烷-3-羧酸 以 四氢呋喃 为溶剂， 生成 (1R,2S,4R,6S,7R)-(+)-3-oxotricyclo<2,2,1,0^2,6>heptane-7-carboxylic acid
  参考文献：
  名称：

  Cervinka, Otakar; Habartova, Eliska, Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 12, p. 3565 - 3566

  摘要：

  DOI：

文献信息

• Total synthesis of racemic 12-methylprostaglandins
  作者：Paul A. Grieco、Chester S. Pogonowski、Steven D. Burke、Mugio Nishizawa、Masaaki Miyashita、Yukio Masaki、C. L. J. Wang、G. Majetich

  DOI：10.1021/ja00454a033

  日期：1977.6
• A new chemoenzymatic synthesis of d-cloprostenol
  作者：Andrea Romano、Diego Romano、Francesco Molinari、Raffaella Gandolfi、Francesca Costantino

  DOI：10.1016/j.tetasy.2005.08.038

  日期：2005.10

  A new chemoenzymatic synthesis Of D-cloprostenol based on the biocatalytical resolution of anti-2-oxotricyclo[2.2.1.0]heptan-7-carboxylic acid 1 has been developed. The resolution was attempted by different approaches: esterification or reduction of the acid and hydrolysis or reduction of the corresponding esters. The most efficient method proved to be the reduction of the propyl esters of 1 catalysed by the yeast Kluyveromyces marxianus, which allowed for the recovery of the enantiomerically pure ester of anti-2-oxotricyclo[2.2.1.0]heptan-(R)-7-carboxylic acid (R)-3 at 60% molar conversion of 3.0 g/l of racemic substrate acid under optimised conditions. anti-2-Oxotricyclo[2.2. 1.0]heptan-(R)-7-carboxylic acid was obtained by alkaline hydrolysis and employed for the synthesis of D-cloprostenol. (c) 2005 Published by Elsevier Ltd.
• Cervinka, Otakar; Habartova, Eliska, Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 12, p. 3565 - 3566
  作者：Cervinka, Otakar、Habartova, Eliska

  DOI：——

  日期：——