[1-(2-Benzyloxy-1-hydroxy-ethyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester | 247089-08-3

• 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: [1-(2-Benzyloxy-1-hydroxy-ethyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[[1-(1-hydroxy-2-phenylmethoxyethyl)cyclohexyl]methyl]carbamate
• CAS: 247089-08-3
• 化学式: C₂₁H₃₃NO₄
• 分子量: 363.497
• InChiKey: YIJCOAURNOHEDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1-(2-Benzyloxy-1-hydroxy-ethyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester 在 ruthenium trichloride 、 sodium periodate 、 palladium 10% on activated carbon 、 甲酸铵 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 2-Aza-spiro[3.5]nonane-1,2-dicarboxylic acid 2-tert-butyl ester
  参考文献：
  名称：

  Azetidines and spiro azetidines as novel P2 units in hepatitis C virus NS3 protease inhibitors

  摘要：

  Herein, we report the synthesis and structure-activity relationship studies of new analogs of boceprevir 1 and telaprevir 2. Introduction of azetidine and spiroazetidines as a P2 substituent that replaced the pyrrolidine moiety of 1 and 2 led to the discovery of a potent hepatitis C protease inhibitor 37c (EC50 = 0.8 mu M). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.068
• 作为产物：
  描述：

  环己甲腈 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 45.0h， 生成 [1-(2-Benzyloxy-1-hydroxy-ethyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Azetidines and spiro azetidines as novel P2 units in hepatitis C virus NS3 protease inhibitors

  摘要：

  Herein, we report the synthesis and structure-activity relationship studies of new analogs of boceprevir 1 and telaprevir 2. Introduction of azetidine and spiroazetidines as a P2 substituent that replaced the pyrrolidine moiety of 1 and 2 led to the discovery of a potent hepatitis C protease inhibitor 37c (EC50 = 0.8 mu M). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.068

文献信息

• Conformationally constrained compounds as pharmaceutical agents
  申请人：Bryans Stephen Justin

  公开号：US20050250800A1

  公开（公告）日：2005-11-10

  Novel substituted amino acids of formula are disclosed and are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, and neuropathological disorders. Processes for the preparation and intermediates useful in the preparation are also disclosed.

  本发明揭示了公式替代氨基酸，并且可用作治疗癫痫、晕厥、低动力、头颅疾病、神经退行性疾病、抑郁症、焦虑症、恐慌症、疼痛和神经病理学疾病的药物。同时还揭示了制备过程和制备中有用的中间体。
• Synthesis and biological evaluation of conformationally restricted gabapentin analogues
  作者：Jean-Marie Receveur、Justin S. Bryans、Mark J. Field、Lakhbir Singh、David C. Horwell

  DOI：10.1016/s0960-894x(99)00383-2

  日期：1999.8

  A series of conformationally restricted Gabapentin analogues has been synthesised. The pyrrolidine analogue (R)-2-Aza-spiro[4.5]decane-4-carboxylic acid hydrochloride (3a) had an IC(50) of 120nM, similar to that of Gabapentin (IC(50) = 140nM), at the Gabapentin binding site on the alpha(2)delta subunit of a calcium channel. Compound (3a) also reversed carrageenan induced hyperalgesia in rats, (C) 1999 Elsevier Science Ltd. All rights reserved.
• US6316638B1
  申请人：——

  公开号：US6316638B1

  公开（公告）日：2001-11-13
• US6489352B2
  申请人：——

  公开号：US6489352B2

  公开（公告）日：2002-12-03
• Azetidines and spiro azetidines as novel P2 units in hepatitis C virus NS3 protease inhibitors
  作者：Lavanya Bondada、Ramu Rondla、Ugo Pradere、Peng Liu、Chengwei Li、Drew Bobeck、Tamara McBrayer、Philip Tharnish、Jerome Courcambeck、Philippe Halfon、Tony Whitaker、Franck Amblard、Steven J. Coats、Raymond F. Schinazi

  DOI：10.1016/j.bmcl.2013.09.068

  日期：2013.12

  Herein, we report the synthesis and structure-activity relationship studies of new analogs of boceprevir 1 and telaprevir 2. Introduction of azetidine and spiroazetidines as a P2 substituent that replaced the pyrrolidine moiety of 1 and 2 led to the discovery of a potent hepatitis C protease inhibitor 37c (EC50 = 0.8 mu M). (C) 2013 Elsevier Ltd. All rights reserved.