(1R,3R)-3-羟基环戊烷羧酸苄酯 | 946152-80-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1R,3R)-3-羟基环戊烷羧酸苄酯
• 英文名称: (1R,3R)-3-hydroxy-cyclopentanecarboxylic acid benzyl ester
• 英文别名: trans-Benzyl 3-hydroxycyclopentanecarboxylate；benzyl (1R,3R)-3-hydroxycyclopentane-1-carboxylate
• CAS: 946152-80-3
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: RDUCOWDKAANTQZ-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (1R,3R)-3-羟基环戊烷羧酸苄酯 在 氢气 、 palladium(II) hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 BMS-457
  参考文献：
  名称：

  The discovery of BMS-457, a potent and selective CCR1 antagonist

  摘要：

  A series of compounds which exhibited good human CCR1 binding and functional potency was modified resulting in the discovery of a novel series of high affinity, functionally potent antagonists of the CCR1 receptor. Issues of PXR activity, ion-channel potency, and poor metabolic stability were addressed by the addition of a hydroxyl group to an otherwise lipophilic area in the molecule resulting in the discovery of preclinical candidate BMS-457 for the treatment of rheumatoid arthritis. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.079
• 作为产物：
  描述：

  苯甲醇 在 4-二甲氨基吡啶 、 Wilkinson's catalyst 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 儿萘酚硼烷 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,3R)-3-羟基环戊烷羧酸苄酯
  参考文献：
  名称：

  The discovery of BMS-457, a potent and selective CCR1 antagonist

  摘要：

  A series of compounds which exhibited good human CCR1 binding and functional potency was modified resulting in the discovery of a novel series of high affinity, functionally potent antagonists of the CCR1 receptor. Issues of PXR activity, ion-channel potency, and poor metabolic stability were addressed by the addition of a hydroxyl group to an otherwise lipophilic area in the molecule resulting in the discovery of preclinical candidate BMS-457 for the treatment of rheumatoid arthritis. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.079

文献信息

• [EN] DIAZENIUMDIOLATE CYCLOPENTYL DERIVATIVES<br/>[FR] DÉRIVÉS DIAZÉNIUMDIOLATE CYCLOPENTYLE
  申请人：MERCK SHARP & DOHME

  公开号：WO2011100384A1

  公开（公告）日：2011-08-18

  A compound having the structure or a pharmaceutically acceptable salt thereof, wherein R1 is hydrogen, -OH, -O-C1-6 alkyl, =O, or halogen;R2 is hydrogen, C(O)OR8, C6H5C(O)OR8, (CH2)1-2OH, CR9R10OH, C(O)O(CH2)0-2 aryl, C(O)NR9R10, C(O)SO2NR9R10, C6H5OR9, W-C(O)OR8, W-OR9, Y, or P(O)(OR9)(ORlO); R3 is hydrogen or -C1-6 alkyl; R4 is hydrogen, -OH or -C(O)OR9; R5 is hydrogen or deuterium; R6 and R7 are independently-C1-6 alkyl, fluoro-substituted -C1-6 alkyl, deutero-substituted -C1-6 alkyl or -(CH2)1-2R11, wherein any carbon atom of the fluoro-substituted -C1-6 alkyl is mono- or di-substituted with fluoro, and any carbon atom of the deutero-substituted -C 1-6 alkyl is mono- or di-substituted with fluoro; R8, in each instance in which it occurs, is independently hydrogen, -C1-6 alkyl, or -(CH2)2N+(CH3)3; R9 and R10, in each instance in which they occur, are independently -C1-6 alkyl; R11 is -OH, -O-C 1-6 alkyl, -0CD3, -OC(O)OC 1-6 alkyl, -NH2, -C6H5, -N3, or W; W is an unsubslituted 5- or 6-raembered heteroaryl ring having 1, 2, or 3 nitrogen atoms, or a substituted 5- or 6-membered heteroaryl ring having 1, 2, or 3 nitrogen atoms that is mono- or di-substituted at any carbon atom with R6 or R7; Y is a 5- or 6-membered heterocyclic ring having 1, 2, 3 or 4 heteroatoms which are N, O or S or stereoisomers thereof, or pharmaceutically acceptable salts thereof, or pharmaceutically acceptable salts of stereoisomers thereof, and methods of using the compounds for treating hypertension.

  具有以下结构或其药用可接受盐的化合物，其中R1为氢、-OH、-O-C1-6烷基、=O或卤素；R2为氢、C(O)OR8、 C(O)OR8、(CH2)1-2OH、CR9R10OH、C(O)O( )0-2芳基、C(O)NR9R10、C(O)SO2NR9R10、 OR9、W-C(O)OR8、W-OR9、Y或P(O)(OR9)(ORlO)；R3为氢或-C1-6烷基；R4为氢、-OH或-C(O)OR9；R5为氢或氘；R6和R7分别为-C1-6烷基、氟代-C1-6烷基、氘代-C1-6烷基或-( )1-2R11，其中氟代-C1-6烷基的任何碳原子是单取代或双取代的氟，氘代-C1-6烷基的任何碳原子是单取代或双取代的氟；R8在每次出现时独立地为氢、-C1-6烷基或-( )2N+(CH3)3；R9和R10在每次出现时独立地为-C1-6烷基；R11为-OH、-O-C1-6烷基、-0CD3、-OC(O)OC1-6烷基、-NH2、-C6H5、-N3或W；W为具有1、2或3个氮原子的未取代的5-或6-成员杂环芳基环，或具有1、2或3个氮原子的在任何碳原子上单取代或双取代的取代的5-或6-成员杂环芳基环；Y为具有1、2、3或4个N、O或S杂原子或其立体异构体的5-或6-成员杂环环，或其药用可接受盐，或其立体异构体的药用可接受盐，以及使用这些化合物治疗高血压的方法。
• Heterocyclic antiviral compounds
  申请人：Lemoine Rcmy

  公开号：US20070191406A1

  公开（公告）日：2007-08-16

  Chemokine receptor antagonists, in particular, 3,7-diazabicyclo[3.3.0]octane compounds according to formula (I) wherein R 1 -R 3 R 6c and X 1 are as defined herein are antagonists of chemokine CCR5 receptors which are useful for treating or preventing an human immunodeficiency virus (HIV) infection, or treating AIDS or ARC. The invention further provides methods for treating diseases that are alleviated with CCR5 antagonists. The invention includes pharmaceutical compositions and methods of using the compounds for the treatment of these diseases. The invention further includes processes for the preparation of compounds according to formula I.

  化学因子受体拮抗剂，特别是根据以下公式（I）的3,7-二氮杂双环[3.3.0]辛烷化合物，其中R1-R3R6c和X1如本文所定义，是化学因子CCR5受体的拮抗剂，可用于治疗或预防人类免疫缺陷病毒（HIV）感染，或治疗艾滋病或ARC。该发明还提供了用于治疗通过CCR5拮抗剂缓解的疾病的方法。该发明包括用于治疗这些疾病的药物组合物和使用这些化合物的方法。该发明还包括根据公式I制备化合物的方法。
• Stereoselective conversion of tetraalkyltin compounds to alcohols
  作者：James W. Herndon、Chao Wu

  DOI：10.1016/s0040-4039(01)88994-2

  日期：1989.1

  A stereoselective method for the conversion of a tributyltin group at an unactivated carbon atom has been achieved. Reaction with bromine leads to preferential cleavage of a butyl group, giving an alkylbromodibutylstannane. Subsequent reaction with basic peroxide leads to preferential cleavage of the more-substituted carbon-tin bond and formation of the corresponding alcohol with retention of configuration

  已经实现了用于在未活化的碳原子上转化三丁基锡基团的立体选择方法。与溴反应导致丁基优先裂解，得到烷基溴二丁基锡烷。随后与碱性过氧化物的反应导致被更多取代的碳-锡键的优先裂解并形成相应的醇并保持构型。
• HEMDON, JAMES W.;WU, CHAO, TETRAHEDRON LETT., 30,(1989) N7, C. 6461-6464
  作者：HEMDON, JAMES W.、WU, CHAO

  DOI：——

  日期：——
• DIAZENIUMDIOLATE CYCLOPENTYL DERIVATIVES
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2533644A1

  公开（公告）日：2012-12-19