2-((S)-1-hydroxyheptyl)cyclohex-2-enone | 866940-64-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-((S)-1-hydroxyheptyl)cyclohex-2-enone
• 英文别名: 2-[(1S)-1-Hydroxyheptyl]-2-cyclohexen-1-one；2-[(1S)-1-hydroxyheptyl]cyclohex-2-en-1-one
• CAS: 866940-64-9
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: CPEAROTXCSPXER-LBPRGKRZSA-N

物化性质

• 沸点：
  346.0±21.0 °C(Predicted)
• 密度：
  1.002±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 庚醛 在 4-二甲氨基吡啶 、 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2S)-2-{[2-({[3,5-bis(trifluoromethyl)phenyl]carbamothioyl}amino)phenyl]sulfanyl}cyclohexyl]thiourea 作用下， 反应 168.0h， 以30%的产率得到2-((S)-1-hydroxyheptyl)cyclohex-2-enone
  参考文献：
  名称：

  Enantiopure trans-1-amino-2-(arylsulfanyl)cyclohexanes: novel chiral motifs for ligands and organocatalysts

  摘要：

  In order to obtain the title compounds (1R,2R)-cyclohexane-1,2-diol was stereoselectively converted into cis-(1R,2S)-2-(arylsulfanyl)cyclohexanols and these products were submitted to the nucleophilic substitution via the Mitsunobu reaction (HN3, DEAD). Reduction of the isolated azides gave the desired trans-(1S,2S)-1-amino-2-(arylsulfanyl)cyclohexanes. The (1S,2S)-1-amino-2-(2-aminophenylsulfanyl)cyclohexanes thus prepared were reacted with 3,5-bis(trifluoromethyl)phenyl isothiocyanate to furnish the respective bis-thiourea compounds. An application of a derivative of this type as an organocatalyst (20 mol %) in the Baylis-Hillman reaction gave the respective product in up to 93% ee. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.09.015

文献信息

• Chiral Binaphthyl-Derived Amine-Thiourea Organocatalyst-Promoted Asymmetric Morita−Baylis−Hillman Reaction
  作者：Jian Wang、Hao Li、Xinhong Yu、Liansuo Zu、Wei Wang

  DOI：10.1021/ol051822+

  日期：2005.9.1

  [reaction: see text] A new bifunctional binaphthyl-derived amine thiourea organocatalyst has been developed to promote enantioselective Morita-Baylis-Hillman reaction of cyclohexenone with a wide range of aldehydes. The process, catalyzed by the amine thiourea, affords synthetically valuable chiral allylic alcohol building blocks in high yields and high enantioselectivities.

  [反应：见正文]已开发出一种新的双官能联萘衍生的胺硫脲有机催化剂，以促进环己烯酮与多种醛的对映选择性森田-贝利斯-希尔曼反应。由胺硫脲催化的该方法以高收率和高对映选择性提供了合成上有价值的手性烯丙基醇结构单元。
• Asymmetric Morita–Baylis–Hillman reactions of 2-cyclohexen-1-one catalyzed by chiral biaryl-based bis(thiourea) organocatalysts
  作者：Yuki Nakayama、Takashi Gotanda、Katsuji Ito

  DOI：10.1016/j.tetlet.2011.09.064

  日期：2011.11

  Newly-developed bis(thiourea) 1d was found to be an efficient organocatalyst for the Morita-Baylis-Hillman reaction. High enantioselectivities were obtained in the reaction of 2-cyclohexen-1-one with both aromatic aldehydes (up to 84% ee) and aliphatic aldehydes (up to 96% ee). (C) 2011 Elsevier Ltd. All rights reserved.
• Thiourea-catalyzed Morita–Baylis–Hillman reaction
  作者：Yoshihiro Sohtome、Nobuko Takemura、Rika Takagi、Yuichi Hashimoto、Kazuo Nagasawa

  DOI：10.1016/j.tet.2008.07.087

  日期：2008.9

  Here, we describe our studies on the thiourea-catalyzed Morita-Baylis-Hillman (MBH) reaction. Chemoselective activation of carbonyl compounds via hydrogen bonding to thiourea as a catalyst is the key to drastic rate acceleration of this reaction. The application of chiral bis-thiourea-type organocatalysts, which can form a chiral double hydrogen-bonding network, is effective for enantioselective MBH reaction. A cooperative system of bis-thiourea compounds, synthesized from 1,2-diaminocyclohexane, and a Lewis base effectively promotes the MBH reaction at lower temperature, affording the MBH adducts in 33-95% yield with 44-90% ee. A plausible transition state model of the enantioselective MBH reaction is presented. (C) 2008 Elsevier Ltd. All rights reserved.