(S)-2-((2-chlorophenyl)(hydroxy)methyl)cyclohex-2-enone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-((2-chlorophenyl)(hydroxy)methyl)cyclohex-2-enone
• 英文别名: 2-((S)-(2-chlorophenyl)(hydroxy)methyl)cyclohex-2-enone；2-[(2-chlorophenyl)hydroxymethyl]cyclohex-2-enone；2-[(S)-(2-chlorophenyl)-hydroxymethyl]cyclohex-2-en-1-one
• 化学式: C₁₃H₁₃ClO₂
• 分子量: 236.698
• InChiKey: HXKZCOAFSNZAPK-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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 、 2-氯苯甲醛 在 (R)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(1-(2-(dimethylamino)naphthalen-1-yl)naphthalen-2-yl)thiourea 作用下， 以 乙腈 为溶剂， 反应 108.0h， 生成 (S)-2-((2-chlorophenyl)(hydroxy)methyl)cyclohex-2-enone 、 2-((R)-(2-chlorophenyl)(hydroxy)methyl)cyclohex-2-enone
  参考文献：
  名称：

  手性联萘衍生的胺-硫脲有机催化剂促进不对称Morita-Baylis-Hillman反应。

  摘要：

  [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。

  DOI：

  10.1021/ol051822+

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。
• A highly efficient kinetic resolution of Morita–Baylis–Hillman adducts achieved by N–Ar axially chiral Pd-complexes catalyzed asymmetric allylation
  作者：Feijun Wang、Shengke Li、Mingliang Qu、Mei-Xin Zhao、Lian-Jun Liu、Min Shi

  DOI：10.1039/c1cc15543a

  日期：——

  Palladium complexes with an axially chiral N–Ar framework have been developed. These complexes showed high stereoselectivities in asymmetric allylic arylation to achieve the kinetic resolution of Morita–Baylis–Hillman adducts, affording up to 99% ee of (E)-allylation products and 92% ee of recovered Morita–Baylis–Hillman adducts.

  我们开发了具有轴向手性 NâAr 框架的钯配合物。这些配合物在不对称烯丙基芳基化过程中表现出很高的立体选择性，从而实现了莫里塔-贝利斯-希尔曼加合物的动力学解析，得到的(E)-烯丙基化产物的ee高达99%，回收的莫里塔-贝利斯-希尔曼加合物的ee高达92%。
• Asymmetric Morita-Baylis-Hillman Reaction of Arylaldehydes with 2-Cyclohexen-1-one Catalyzed by Chiral Bis(Thio)urea and DABCO
  作者：Min Shi、Xu-Guang Liu

  DOI：10.1021/ol7028806

  日期：2008.3.1

  Novel bis(thio)urea organocatalysts were synthesized from axially chiral (R)-(-)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diamine (H-8-BINAM), and their catalytic abilities have been examined in the Morita-Baylis-Hillman reaction of 2-cyclohexen-1-one or 2-cyclopenten-1-one with a wide range of aromatic aldehydes in combination with DABCO. The best result was achieved in the reaction of 3-fluorobenzaldehyde with 2-cyclohexen-1-one to give the desired Morita-Baylis-Hillman product in 79% yield and 88% ee.
• Asymmetric Morita–Baylis–Hillman reaction catalyzed by pepsin
  作者：Jing-Wen Xue、Jian Song、Ian C.K. Manion、Yan-Hong He、Zhi Guan

  DOI：10.1016/j.molcatb.2015.12.002

  日期：2016.2

  Pepsin from porcine gastric mucous shown catalytic promiscuity was first discovered to catalyze the Morita-Baylis-Hillman (MBH) reaction between aromatic aldehydes with 2-cyclohexen-1-one or 2-cyclopenten-i-one in a two-phase medium of phosphate buffer/cyclohexane in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO). The best results of the corresponding MBH products up to 77% yield and 38% ee were achieved. (C) 2015 Elsevier B.V. All rights reserved.