methyl 1-(1-phenylethane)cyclohexanecarboxylate | 1081992-08-6

• 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: methyl 1-(1-phenylethane)cyclohexanecarboxylate
• 英文别名: methyl 1-(1-phenylethyl)-cyclohexanecarboxylate；methyl 1-(1-phenylethyl)cyclohexanecarboxylate；Methyl 1-(1-phenylethyl)cyclohexane-1-carboxylate；methyl 1-(1-phenylethyl)cyclohexane-1-carboxylate
• CAS: 1081992-08-6
• 化学式: C₁₆H₂₂O₂
• 分子量: 246.349
• InChiKey: WUKWBSGBBVHDAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 1-(1-phenylethane)cyclohexanecarboxylate 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 1-(1-Phenylethyl)cyclohexanecarboxylic acid
  参考文献：
  名称：

  The introduction of P4 substituted 1-methylcyclohexyl groups into Boceprevir®: A change in direction in the search for a second generation HCV NS3 protease inhibitor

  摘要：

  In the search for a second generation HCV protease inhibitor, molecular modeling studies of the X-ray crystal structure of Boceprevir (R) 1 bound to the NS3 protein suggest that expansion into the S4 pocket could provide additional hydrophobic Van der Waals interactions. Effective replacement of the P4 tertbutyl with a cyclohexylmethyl ligand led to inhibitor 2 with improved enzyme and replicon activities. Subsequent modeling and SAR studies led to the pyridine 38 and sulfone analogues 52 and 53 with vastly improved PK parameters in monkeys, forming a new foundation for further exploration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.063
• 作为产物：
  描述：

  苯乙烯 、 1-methoxy-1-trimethylsilyloxymethylenecyclohexane 在 indium(III) bromide 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以68%的产率得到methyl 1-(1-phenylethane)cyclohexanecarboxylate
  参考文献：
  名称：

  三溴化铟和丁烯基甲硅烷基缩醛对简单烯烃的区域选择性碳环化

  摘要：

  简单的烯烃与三溴化铟和乙烯酮甲硅烷基乙缩醛的区域选择性碳键合成。各种烯烃如乙烯，1-烯烃和环状烯烃可用于该反应体系。来自环己烯碳环化的烷基铟产物显示出抗加成机理。

  DOI：

  10.1021/ol1012108

文献信息

• Synthesis of Alkylbismuths by Regiodivergent Carbobismuthination of Simple Alkenes
  作者：Yoshihiro Nishimoto、Midori Takeuchi、Makoto Yasuda、Akio Baba

  DOI：10.1002/chem.201302194

  日期：2013.10.18

  Switchable regioselectivity: This study represents the first carbobismuthination of alkenes achieved by the treatment of an alkene with a bismuth halide and a ketene silyl acetal. This reaction is particularly noteworthy in that a change in the type of halogen on a bismuth atom very easily switched the regioselectivity (see scheme).

  可切换的区域选择性：这项研究代表了通过卤化铋和乙烯酮甲硅烷基乙缩醛处理烯烃而实现的烯烃的第一次碳羰基甲基化。该反应特别值得注意，因为铋原子上卤素类型的变化很容易改变区域选择性（参见方案）。
• Indium-catalyzed coupling reaction between silyl enolates and alkyl chlorides or alkyl ethers
  作者：Yoshihiro Nishimoto、Takahiro Saito、Makoto Yasuda、Akio Baba

  DOI：10.1016/j.tet.2009.03.106

  日期：2009.7

  The coupling reactions of alkyl chlorides with silyl enolates catalyzed by InBr3, and the coupling reactions of alkyl ethers with silyl enolates catalyzed by the combined Lewis acid of InBr3/Me3SiBr are described. In both reaction systems, various types of silyl enolates were used to give corresponding α-alkylated esters, ketones, carboxylic acids, amides, thioesters, and aldehydes.

  描述了烷基氯化物与InBr 3催化的烯醇硅酸酯的偶联反应，以及烷基醚与InBr 3 / Me 3 SiBr的路易斯酸催化的烯醇硅酸酯的偶联反应。在两个反应系统中，都使用了各种类型的甲硅烷基烯酸酯，以生成相应的α-烷基化的酯，酮，羧酸，酰胺，硫代酯和醛。
• Regioselective Carboindation of Simple Alkenes with Indium Tribromide and Ketene Silyl Acetals
  作者：Yoshihiro Nishimoto、Hiroki Ueda、Yoshihiro Inamoto、Makoto Yasuda、Akio Baba

  DOI：10.1021/ol1012108

  日期：2010.8.6

  The regioselective carboindation of simple alkenes with indium tribromide and ketene silyl acetals was accomplished. Various alkenes such as ethylene, 1-alkenes, and cyclic alkenes were applicable for this reaction system. The alkylindium product from the carboindation of cyclohexene revealed an anti addition mechanism.

  简单的烯烃与三溴化铟和乙烯酮甲硅烷基乙缩醛的区域选择性碳键合成。各种烯烃如乙烯，1-烯烃和环状烯烃可用于该反应体系。来自环己烯碳环化的烷基铟产物显示出抗加成机理。
• The introduction of P4 substituted 1-methylcyclohexyl groups into Boceprevir®: A change in direction in the search for a second generation HCV NS3 protease inhibitor
  作者：Frank Bennett、Yuhua Huang、Siska Hendrata、Raymond Lovey、Stephane L. Bogen、Weidong Pan、Zhuyan Guo、Andrew Prongay、Kevin X. Chen、Ashok Arasappan、Srikanth Venkatraman、Francisco Velazquez、Latha Nair、Mousumi Sannigrahi、Xiao Tong、John Pichardo、Kuo-Chi Cheng、Viyyoor M. Girijavallabhan、Anil K. Saksena、F. George Njoroge

  DOI：10.1016/j.bmcl.2010.02.063

  日期：2010.4

  In the search for a second generation HCV protease inhibitor, molecular modeling studies of the X-ray crystal structure of Boceprevir (R) 1 bound to the NS3 protein suggest that expansion into the S4 pocket could provide additional hydrophobic Van der Waals interactions. Effective replacement of the P4 tertbutyl with a cyclohexylmethyl ligand led to inhibitor 2 with improved enzyme and replicon activities. Subsequent modeling and SAR studies led to the pyridine 38 and sulfone analogues 52 and 53 with vastly improved PK parameters in monkeys, forming a new foundation for further exploration. (C) 2010 Elsevier Ltd. All rights reserved.