(3S,4S)-3-isopropenyl-3-(2-hydroxyethyl)-4-methylcyclopentanone | 335594-96-2

• 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-isopropenyl-3-(2-hydroxyethyl)-4-methylcyclopentanone
• 英文别名: (3S,4S)-3-(2-hydroxyethyl)-4-methyl-3-prop-1-en-2-ylcyclopentan-1-one
• CAS: 335594-96-2
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: KLMPBHDVRDYEHY-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-isopropenyl-3-(2-hydroxyethyl)-4-methylcyclopentanone 在 Wilkinson's catalyst sodium acetate 、 pyridinium chlorochromate 作用下， 以 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：

  (3S,4S)-3-(2-acetoxyethyl)-3-isopropenyl-4-methylcyclopentanone 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以100%的产率得到(3S,4S)-3-isopropenyl-3-(2-hydroxyethyl)-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

• Enantio- and diastereoselective construction of 4,9-dimethylspiro[4.4]nonane-2,7-dione using Rh-catalyzed asymmetric cyclization
  作者：Masakazu Tanaka、Miyuki Takahashi、Eishi Sakamoto、Masanori Imai、Akiko Matsui、Masakazu Fujio、Kazuhisa Funakoshi、Kiyoshi Sakai、Hiroshi Suemune

  DOI：10.1016/s0040-4020(00)01106-6

  日期：2001.2

  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.