methyl 1-[hydroxy(phenyl)methyl]cyclohexanecarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 1-[hydroxy(phenyl)methyl]cyclohexanecarboxylate
• 英文别名: Methyl 1-[hydroxy(phenyl)methyl]cyclohexane-carboxylate；methyl 1-[hydroxy(phenyl)methyl]cyclohexane-1-carboxylate
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: LZUQSGHQXAKWMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-[hydroxy(phenyl)methyl]cyclohexanecarboxylate 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 1-[羟基(苯基)甲基]环己烷-1-羧酸
  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：

  环己甲酸甲酯 在 zinc chloride on alumina 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 methyl 1-[hydroxy(phenyl)methyl]cyclohexanecarboxylate
  参考文献：
  名称：

  Surface-Mediated Solid Phase Reaction. IX. A Convenient Procedure for Aldol Reaction of Ketene Silyl Acetals with Aldehydes on the Solid Surface of Alumina

  摘要：

  The aldol reaction of ketene silyl acetals with aldehydes proceeds efficiently on the solid surface of alumina impregnated with anhydrous zinc chloride under sonication providing aldol products in high yields and with good stereoselectivity.

  DOI：

  10.1080/00397919708005012

文献信息

• Photoredox‐Catalyzed Generation of Tertiary Anions from Primary Amines via a Radical Polar Crossover
  作者：Austin D. Marchese、Julia R. Dorsheimer、Tomislav Rovis

  DOI：10.1002/anie.202317563

  日期：2024.2.5

  radical-polar crossover strategy generating carbanions is reported. This so called “aza-Reformatsky” reaction leverages the use of redox-active imines and an iridium photocatalyst to generate a wide array of tertiary benzylic, heteroarylbenzylic and α-ester anions, which can be trapped with different electrophiles.

  报道了一种产生碳负离子的脱氨基自由基-极性交叉策略。这种所谓的“aza-Reformatsky”反应利用氧化还原活性亚胺和铱光催化剂产生多种叔苄基、杂芳基苄基和α-酯阴离子，这些阴离子可以被不同的亲电子试剂捕获。
• Synthesis of 16-aryl-15-oxadispiro[5.1.5.3]hexadecane-7,14-diones by reformatsky reaction
  作者：N. F. Kirillov、E. A. Nikiforova、A. N. Vasyanin、M. V. Dmitriev

  DOI：10.1134/s1070428015040089

  日期：2015.4

  Methyl 1-bromocyclohexanecarboxylate reacted with zinc and aromatic aldehydes in two steps to afford 16-aryl-15-oxadispiro[5.1.5.3]hexadecane-7,14-diones; methyl 1-[aryl(hydroxy)methyl]cyclohexanecarboxylates were also formed as by-products.
• Surface-Mediated Solid Phase Reaction. IX. A Convenient Procedure for Aldol Reaction of Ketene Silyl Acetals with Aldehydes on the Solid Surface of Alumina
  作者：Brindaban C. Ranu、Manika Saha、Sanjay Bhar

  DOI：10.1080/00397919708005012

  日期：1997.9

  The aldol reaction of ketene silyl acetals with aldehydes proceeds efficiently on the solid surface of alumina impregnated with anhydrous zinc chloride under sonication providing aldol products in high yields and with good stereoselectivity.
• 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.