(R)-6-Isopropyl-cyclohex-2-enone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-6-Isopropyl-cyclohex-2-enone
• 英文别名: (6R)-6-propan-2-ylcyclohex-2-en-1-one
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: RDSYFWVRUCJTON-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-6-Isopropyl-cyclohex-2-enone 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (+)-薄荷酮 、 (+)-异薄荷酮
  参考文献：
  名称：

  Kinetic Resolution of cis-3-Alkylcyclohexene Oxide by a Chiral Lithium Amide - An Application to a Synthesis of Both Enantiomers of Isomenthon -

  摘要：

  Kinetic resolution of cis-3-alkylcyclohexene oxide (1) was examined using chiral lithium amide, lithium (S)-2-(pyrrolidin-1-yl)methylpyrrolidide (2). High cc (84-->98% eel of 1 was obtained by using 1.1-1.2 equiv of 2, while 6-alkyl-2-cyclohexenol (3) was obtained in moderate ee (60-68% eel by using 0.5-0.75 equiv of 2. Both enantiomers of cis-2-isopropyl-5-methylcyclohexanone (isomenthone)were derived from (1S,2R,3R)-(+)-3-isopropylcyclohexene oxide (1b) or (1R,6R)-(-)-6-isopropyl-2-cyclohexenol (3b) in a few steps, respectively.

  DOI：

  10.3987/com-99-s122
• 作为产物：
  描述：

  (1S*,2R*,3R*)-3-isopropyl-1,2-epoxycyclohexane 在 manganese(IV) oxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 Lithium (S)-2-(1-pyrrolidinylmethyl)pyrrolidide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (R)-6-Isopropyl-cyclohex-2-enone
  参考文献：
  名称：

  Kinetic Resolution of cis-3-Alkylcyclohexene Oxide by a Chiral Lithium Amide - An Application to a Synthesis of Both Enantiomers of Isomenthon -

  摘要：

  Kinetic resolution of cis-3-alkylcyclohexene oxide (1) was examined using chiral lithium amide, lithium (S)-2-(pyrrolidin-1-yl)methylpyrrolidide (2). High cc (84-->98% eel of 1 was obtained by using 1.1-1.2 equiv of 2, while 6-alkyl-2-cyclohexenol (3) was obtained in moderate ee (60-68% eel by using 0.5-0.75 equiv of 2. Both enantiomers of cis-2-isopropyl-5-methylcyclohexanone (isomenthone)were derived from (1S,2R,3R)-(+)-3-isopropylcyclohexene oxide (1b) or (1R,6R)-(-)-6-isopropyl-2-cyclohexenol (3b) in a few steps, respectively.

  DOI：

  10.3987/com-99-s122

文献信息

• Kinetic Resolution of cis-3-Alkylcyclohexene Oxide by a Chiral Lithium Amide - An Application to a Synthesis of Both Enantiomers of Isomenthon -
  作者：Masatoshi Asami、Shinsuke Sato、Kiyoshi Honda、Seiichi Inoue

  DOI：10.3987/com-99-s122

  日期：——

  Kinetic resolution of cis-3-alkylcyclohexene oxide (1) was examined using chiral lithium amide, lithium (S)-2-(pyrrolidin-1-yl)methylpyrrolidide (2). High cc (84-->98% eel of 1 was obtained by using 1.1-1.2 equiv of 2, while 6-alkyl-2-cyclohexenol (3) was obtained in moderate ee (60-68% eel by using 0.5-0.75 equiv of 2. Both enantiomers of cis-2-isopropyl-5-methylcyclohexanone (isomenthone)were derived from (1S,2R,3R)-(+)-3-isopropylcyclohexene oxide (1b) or (1R,6R)-(-)-6-isopropyl-2-cyclohexenol (3b) in a few steps, respectively.