(1S,2R,3S,4S)-3-methyl-6-oxobicyclo[2.2.1]heptane-2-carboxylic acid | 131432-95-6

• 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: (1S,2R,3S,4S)-3-methyl-6-oxobicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 131432-95-6
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: ZPXJBAQVSQWOSW-LZCNBPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4S)-3-methyl-6-oxobicyclo[2.2.1]heptane-2-carboxylic acid 在 氢气 、 lithium diisopropyl amide 作用下， 生成 (1S,2R,3S,4R,5S)-3,5-Dimethyl-6-oxo-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester
  参考文献：
  名称：

  降冰片烯-6-一-2-羧酸酯的还原裂解合成维生素D 3 D环合成子

  摘要：

  在液态氨中用锂金属对5-甲基降冰片烷-6-一-2-羧酸酯进行的还原裂解，得到了3-（1-甲基-2-甲氧基羰基乙基）环戊烷，收率很高。

  DOI：

  10.1016/s0040-4039(00)97763-3
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 生成 (1S,2R,3S,4S)-3-methyl-6-oxobicyclo[2.2.1]heptane-2-carboxylic acid
  参考文献：
  名称：

  Beckmann et al., Chemische Berichte, 1959, vol. 92, p. 2419,2425

  摘要：

  DOI：

文献信息

• Stereoselective synthesis of cyclopentanones by reductive cleavage of 6-oxonorbornane-2-carboxylates and its application to the synthesis of 1.alpha.,25-dihydroxyvitamin D3 CD ring
  作者：Kazuo Nagasawa、Naoto Matsuda、Yasuo Noguchi、Masahiro Yamanashi、Yoshiro Zako、Isao Shimizu

  DOI：10.1021/jo00058a032

  日期：1993.3

  A novel chiral synthesis of the CD-ring 2 of 1alpha,25-dihydroxyvitamin D3 (1a) is described. The optically active D-ring keto ester 3c was prepared by reductive cleavage of 6-oxonorbornane-2-carboxylate 4c with lithium naphthalenide. 1,2-Transposition of enone 15, which was obtained by Robinson annulation of 14, was accomplished via thermolysis of the allylic carbonate 29 at 100-degrees-C to give enone 16. Reduction of ketone 16 with NaBH4-CeCl3 followed by hydrogenation with RhCl-(PPh3)3 catalyst gave trans-indanol 32, which was transformed to intermediate 2.
• SHIMIZU, ISAO;MATSUDA, NAOTO;NOGUCHI, YASUO;ZAKO, YOSHIRO;NAGASAWA, KAZUO, TETRAHEDRON LETT. , 31,(1990) N4, C. 4899-4902
  作者：SHIMIZU, ISAO、MATSUDA, NAOTO、NOGUCHI, YASUO、ZAKO, YOSHIRO、NAGASAWA, KAZUO

  DOI：——

  日期：——
• Synthesis of vitamin D3 D ring synthons by reductive cleavage of norbornan-6-one-2-carboxylates
  作者：Isao Shimizu、Naoto Matsuda、Yasuo Noguchi、Yoshiro Zako、Kazuo Nagasawa

  DOI：10.1016/s0040-4039(00)97763-3

  日期：1990.1

  Reductive cleavage of 5-methylnorbornan-6-one-2-carboxylates with lithium metal in liquid ammonia gave 3-(1-methyl-2-methoxycarbonylethyl)cyclopentanones in good yields.

  在液态氨中用锂金属对5-甲基降冰片烷-6-一-2-羧酸酯进行的还原裂解，得到了3-（1-甲基-2-甲氧基羰基乙基）环戊烷，收率很高。
• Beckmann et al., Chemische Berichte, 1959, vol. 92, p. 2419,2425
  作者：Beckmann et al.

  DOI：——

  日期：——