(3S,4S)-3-(2-acetoxyethyl)-3-isopropenyl-4-methylcyclopentanone | 335594-93-9

• 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: (3S,4S)-3-(2-acetoxyethyl)-3-isopropenyl-4-methylcyclopentanone
• 英文别名: 2-[(1S,2S)-2-methyl-4-oxo-1-prop-1-en-2-ylcyclopentyl]ethyl acetate
• CAS: 335594-93-9
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: YBQUTNJGARTJRW-GXFFZTMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-(2-acetoxyethyl)-3-isopropenyl-4-methylcyclopentanone 在 Wilkinson's catalyst sodium acetate 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (4S,5R,9S)-4,9-dimethylspiro[4.4]nonane-2,7-dione
  参考文献：
  名称：

  Enantio- and diastereoselective construction of 4,9-dimethylspiro[4.4]nonane-2,7-dione using Rh-catalyzed asymmetric cyclization

  摘要：

  Asymmetric cyclization using Rh-complexes was applied to the synthesis of 4,9-dimethylspiro[4.4]nonane-2,7-diones. The spiro[4.4]nonane skeleton bearing a chiral quaternary carbon could be stepwisely constructed by using Rh-catalyzed cyclization twice. All diastereomers of the spirodiketone could be stereoselectively prepared from the identical starting material by the combination of a neutral Rh(PPh3)(3)Cl and a cationic Rh[BINAP]ClO4. The cyclization by the neutral Rh(PPh3)(3)Cl proceeded to give cis-3,4-disubstituted cyclopentanones, while that by the cationic Rh[BINAP]ClO4 proceeded to afford trans-3,4-disubstituted cyclopentanones. Four spirodiketones of six stereoisomers could be prepared in optically active form, and the relationship between the stereochemistry of the spirodiketones and the Rh-complex was discussed based on the plausible acyl-hydride Rh-complexes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01106-6
• 作为产物：
  描述：

  5-acetoxy-3,3-diisopropenyl-1-pentanol 在 [Rh(R)-BINAP]ClO₄ sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (3S,4S)-3-(2-acetoxyethyl)-3-isopropenyl-4-methylcyclopentanone
  参考文献：
  名称：

  Enantio- and diastereoselective construction of 4,9-dimethylspiro[4.4]nonane-2,7-dione using Rh-catalyzed asymmetric cyclization

  摘要：

  Asymmetric cyclization using Rh-complexes was applied to the synthesis of 4,9-dimethylspiro[4.4]nonane-2,7-diones. The spiro[4.4]nonane skeleton bearing a chiral quaternary carbon could be stepwisely constructed by using Rh-catalyzed cyclization twice. All diastereomers of the spirodiketone could be stereoselectively prepared from the identical starting material by the combination of a neutral Rh(PPh3)(3)Cl and a cationic Rh[BINAP]ClO4. The cyclization by the neutral Rh(PPh3)(3)Cl proceeded to give cis-3,4-disubstituted cyclopentanones, while that by the cationic Rh[BINAP]ClO4 proceeded to afford trans-3,4-disubstituted cyclopentanones. Four spirodiketones of six stereoisomers could be prepared in optically active form, and the relationship between the stereochemistry of the spirodiketones and the Rh-complex was discussed based on the plausible acyl-hydride Rh-complexes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01106-6

文献信息

• Application of Rh-catalyzed cyclization for the construction of three consecutive chiral carbons in 4,9-dimethylspiro[4.4]nonane-2,7-dione
  作者：Miyuki Takahashi、Masakazu Tanaka*、Eishi Sakamoto、Masanori Imai、Akiko Matsui、Kazuhisa Funakoshi、Kiyoshi Sakai、Hiroshi Suemune

  DOI：10.1016/s0040-4039(00)01315-0

  日期：2000.10

  Asymmetric cyclization using Rh-complexes has been applied to the synthesis of 4,9-dimethylspiro[4.4]nonane-2,7-diones. The spiro[4.4]nonane skeleton bearing three consecutive chiral carbons could be stepwisely constructed from an identical starting material by the combination of a cationic Rh[(S)BINAP]ClO4 and a neutral RhCl(PPh3)(3). The relationship between the stereochemistry of the spirodiketones and the Rh-complex was also discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.