(R)-5-methyl-bicyclo<3.3.0>octen-3-one | 244633-47-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-5-methyl-bicyclo<3.3.0>octen-3-one
• 英文别名: (R)-5-methyl-1-bicyclo[3.3.0]octen-3-one；(3aR)-3a-methyl-3a,4,5,6-tetrahydro-2(3H)-pentalenone；(6aR)-6a-methyl-1,4,5,6-tetrahydropentalen-2-one
• CAS: 244633-47-4
• 化学式: C₉H₁₂O
• 分子量: 136.194
• InChiKey: VMPPVSQJDLMPCW-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• 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)-5-methyl-bicyclo<3.3.0>octen-3-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以95%的产率得到cis-hexahydro-3a-methylpentalen-2(1H)-one
  参考文献：
  名称：

  Nitroalkenes as electrophiles in the asymmetric Michael reaction involving chiral imines/enamino esters

  摘要：

  Addition of 2-nitropropene to the chiral imine derived from 2-methylcyclopentanone and (S)-1-phenylethylamine furnished the expected Michael adduct. The latter compound was then efficiently converted into (R)-pentalenone through a Nef reaction. Condensation of the enamino ester derived from 2-carbethoxycyclopentanone and (S)-1-phenylethylamine with 1-nitropropene gave with excellent diastereo- and enantioselectivity the corresponding Michael adduct. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00180-9
• 作为产物：
  描述：

  (R)-2-methyl-2-(2-oxopropyl)cyclopentanone 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 2.0h， 以75%的产率得到(R)-5-methyl-bicyclo<3.3.0>octen-3-one
  参考文献：
  名称：

  Nitroalkenes as electrophiles in the asymmetric Michael reaction involving chiral imines/enamino esters

  摘要：

  Addition of 2-nitropropene to the chiral imine derived from 2-methylcyclopentanone and (S)-1-phenylethylamine furnished the expected Michael adduct. The latter compound was then efficiently converted into (R)-pentalenone through a Nef reaction. Condensation of the enamino ester derived from 2-carbethoxycyclopentanone and (S)-1-phenylethylamine with 1-nitropropene gave with excellent diastereo- and enantioselectivity the corresponding Michael adduct. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00180-9

文献信息

• Asymmetric Synthesis of Bicyclic Ketones Having an Angular Substituent via Ti(II) Alkoxide-Mediated Tandem Cyclization of Trisubstituted Olefinic Substrates
  作者：Hirokazu Urabe、Daigaku Hideura、Fumie Sato

  DOI：10.1021/ol9904038

  日期：2000.2.1

  [reaction: see text] Angularly substituted, optically active bicyclic ketones of up to 94% ee were prepared by the Ti(II) alkoxide-mediated tandem cyclization of open-chain substrates, that is, 8-phenylmenthyl enynoates having a trisubstituted double bond.

  [反应：参见正文]通过Ti（II）醇盐介导的开链底物的串联环化反应制备了高达94％ee的角取代的旋光双环酮，即具有三取代双键的8-苯基薄荷基烯酸酯。
• On the stereochemistry of photoaddition between α,β-unsaturated ketones and olefins—II
  作者：Giovanna Marini-Bettòlo、Soumya P. Sahoo、Gerald A. Poulton、Thomas Y.R. Tsai、Karel Wiesner

  DOI：10.1016/s0040-4020(01)93683-x

  日期：1980.1

  Some years ago an empirical rule, which allows the prediction of product stereochemistry in cis-photocycloaddition reactions of α,β-unsaturated ketones and olefins was tentatively proposed. Several additional examples, both selected from the literature and synthesized in our laboratory, seem to strengthen the validity of the rule.

  几年前，尝试性地提出了一条经验规则，该规则可以预测α，β-不饱和酮与烯烃的顺-光环加成反应中的产物立体化学。从文献中选择并在我们的实验室中合成的几个其他示例似乎增强了该规则的有效性。
• Nitroalkenes as electrophiles in the asymmetric Michael reaction involving chiral imines/enamino esters
  作者：Cyrille Thominiaux、Sébastien Roussé、Didier Desmaële、Jean d'Angelo、Claude Riche

  DOI：10.1016/s0957-4166(99)00180-9

  日期：1999.5

  Addition of 2-nitropropene to the chiral imine derived from 2-methylcyclopentanone and (S)-1-phenylethylamine furnished the expected Michael adduct. The latter compound was then efficiently converted into (R)-pentalenone through a Nef reaction. Condensation of the enamino ester derived from 2-carbethoxycyclopentanone and (S)-1-phenylethylamine with 1-nitropropene gave with excellent diastereo- and enantioselectivity the corresponding Michael adduct. (C) 1999 Elsevier Science Ltd. All rights reserved.