(+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)cyclopentan-1-one | 313502-76-0

• 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: (+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)cyclopentan-1-one
• 英文别名: (3S,4S)-3-(3-fluorophenyl)-4-(hydroxymethyl)cyclopentanone；(+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)cyclopentanone；(+)-trans-3-(S)-hydroxymethyl-4-(S)-(3-fluorophenyl)cyclopentanone；(3S,4S)-3-(3-fluorophenyl)-4-(hydroxymethyl)cyclopentan-1-one
• CAS: 313502-76-0
• 化学式: C₁₂H₁₃FO₂
• 分子量: 208.232
• InChiKey: ZOTZZZACPUECKH-BXKDBHETSA-N

物化性质

• 沸点：
  341.5±37.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)cyclopentan-1-one 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (+)-trans-1-t-butyldimethylsilyloxymethyl-4-oxo-2-(3-fluorophenyl)cyclopentane
  参考文献：
  名称：

  Cyclopentyl modulators of chemokine receptor activity

  摘要：

  公式（I）中的环戊基化合物是趋化因子受体活性的调节剂：其中在公式（I）中，D、G、R2、R3和R8的定义如下。这些化合物及其药用盐和各个对映体在治疗和预防HIV感染、延缓艾滋病发作以及治疗艾滋病方面具有用途。这些化合物也适用于治疗其他通过趋化因子受体介导的疾病和症状。

  公开号：

  US20050070609A1
• 作为产物：
  描述：

  methyl (5S)-5-(3-fluorophenyl)-3-oxo-6-heptenoate 在 sodium hydroxide 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 4-乙酰氨基苯磺酰叠氮 、 三乙胺 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 生成 (+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)cyclopentan-1-one
  参考文献：
  名称：

  Development of a New and Practical Route to Chiral 3,4-Disubstituted Cyclopentanones:  Asymmetric Alkylation and Intramolecular Cyclopropanation as Key C−C Bond-Forming Steps

  摘要：

  An efficient and practical asymmetric synthesis of (+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)cyclopentanone (1) is described. An asymmetric Mo-catalyzed alkylation reaction was used to establish the first stereocenter and a Cu-catalyzed intramolecular diastereoselective cyclopropanation reaction was used to set the second stereocenter. The last step involved a one-pot ring-opening/deprotection/hydrolysis/decarboxylation sequence that furnished the desired product in good yield.

  DOI：

  10.1021/jo025890a

文献信息

• N-cyclopentyl modulators of chemokine receptor activity
  申请人：Merck & Co., Inc.

  公开号：US06358979B1

  公开（公告）日：2002-03-19

  The present invention is directed to compounds of the formula I: (wherein R1, R3, R4, R5, R6, R7, R8, X, n, x and y are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CCR-3.

  本发明涉及以下式I的化合物：（其中R1、R3、R4、R5、R6、R7、R8、X、n、x和y在此处定义），这些化合物可用作趋化因子受体活性调节剂。具体而言，这些化合物可用作趋化因子受体CCR-5和/或CCR-3的调节剂。
• Alkyl C−O Ring Cleavage of Bicyclic β-Lactones with Normant Reagents:  Synthesis of a Merck IND Intermediate
  作者：Wei Zhang、Andrea S. Matla、Daniel Romo

  DOI：10.1021/ol070572p

  日期：2007.5.1

  diastereoselective Cu(I)-mediated, bicyclic beta-lactone ring cleavage reactions with either alkyl or aryl cuprates proceeded with inversion of stereochemistry to give optically active trans-substituted cyclopentanes and cyclohexanes. Optimization of typically problematic aryl cuprate additions was made possible by minimization of a competing bromide-induced ring cleavage process. The utility of this process

  与烷基或芳基铜酸盐的高度非对映选择性的Cu（I）介导的双环β-内酯环裂解反应进行立体化学转化，得到旋光性的反式取代环戊烷和环己烷。通过最小化竞争性溴化物诱导的环裂解过程，可以优化通常有问题的芳基铜酸盐的添加。通过有效合成抗HIV CCR5拮抗剂的默克研究新药（IND）中间体，证明了该方法的实用性。
• Process for preparing 3-hydroxymethyl-4-(aryl or heterocyclic)-cyclopentanones
  申请人：——

  公开号：US20020016492A1

  公开（公告）日：2002-02-07

  Processes are disclosed for preparing 3-hydroxymethylcyclopentanone compounds, which are useful as intermediates in the preparation of HIV chemokine CCR-5 receptor antagonists. A process is described in which the compounds are prepared by opening the cyclopropyl ring of a (1-alkoxycarbonyl-2-oxo)-trans-bicyclo[3.1.0]hexane compound by addition of a nucleophile to the cyclopropyl ring, and then decarboxylating the resulting 2-alkoxycarbonyl-3-(Nu-methyl)-cyclopentanone (Nu=the added nucleophilic group) via base solvolysis. Also described is a process for preparing the bicyclo[3.1.0]hexane precursors by the catalyzed cyclopropanation of a suitable alpha-diazo-beta-ketoester. The preparation of the alpha-diazo-beta-ketoesters and precursors thereto are also disclosed.

  本文介绍了制备3-羟甲基环戊酮化合物的方法，这些化合物在制备HIV趋化因子CCR-5受体拮抗剂中作为中间体非常有用。其中一种方法是通过将核试剂加到环丙基环的(1-烷氧羰基-2-氧代)-反式双环[3.1.0]己烷化合物上，打开环丙基环，然后通过碱溶解解羧基化反应，将产生的2-烷氧羰基-3-(Nu-甲基)-环戊酮（Nu为添加的核试剂基团）脱羧而制备。此外，还介绍了通过催化的α-重氮基-β-酮酸酯环丙烷化反应制备双环[3.1.0]己烷前体的方法。同时也揭示了α-重氮基-β-酮酸酯和其前体的制备方法。
• [EN] N-CYCLOPENTYL MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] MODULATEURS N-CYCLOPENTYLIQUES DE L'ACTIVITE DU RECEPTEUR DE LA CHIMIOKINE
  申请人：MERCK & CO INC

  公开号：WO2000076972A1

  公开（公告）日：2000-12-21

  The present invention is directed to compounds of formula (I) (wherein R?1, R3, R4, R5, R6, R7, R8¿, X, n, x and y are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CCR-3.

  本发明涉及式(I)的化合物（其中R?1，R3，R4，R5，R6，R7，R8¿，X，n，x和y在此定义），其作为趋化因子受体活性调节剂是有用的。特别地，这些化合物是趋化因子受体CCR-5和/或CCR-3的调节剂。
• N-CYCLOPENTYL MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：Merck & Co., Inc.

  公开号：EP1192133B1

  公开（公告）日：2006-11-02