methyl (5S)-2-diazo-5-(3-fluorophenyl)3-oxo-6-heptenoate | 395065-68-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (5S)-2-diazo-5-(3-fluorophenyl)3-oxo-6-heptenoate
• 英文别名: methyl (5S)-5-(3-fluorophenyl)-2-diazo-3-oxohept-6-enoate；Methyl (5S)-5-(3-fluorophenyl)-2-diazo-3-oxohept-6-enoate；methyl (5S)-2-diazo-5-(3-fluorophenyl)-3-oxohept-6-enoate
• CAS: 395065-68-6
• 化学式: C₁₄H₁₃FN₂O₃
• 分子量: 276.267
• InChiKey: LWNKLRMOVKVBBQ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (5S)-2-diazo-5-(3-fluorophenyl)3-oxo-6-heptenoate 在 sodium hydroxide 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 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
• 作为产物：
  描述：

  1-(3-氟苯基)丙-2-烯基甲基碳酸酯 在 盐酸 、 hexacarbonyl molybdenum 、 4-乙酰氨基苯磺酰叠氮 、 三乙胺 、 N,N'-羰基二咪唑 、 magnesium chloride 、 (1S,2S)-1,2-二(2-吡啶碳酰胺)环己烷 作用下， 以 水 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 35.5h， 生成 methyl (5S)-2-diazo-5-(3-fluorophenyl)3-oxo-6-heptenoate
  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：US06593346B2

  公开（公告）日：2003-07-15

  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.

  本发明涉及公式I的化合物：（其中R1，R3，R4，R5，R6，R7，R8，X，n，x和y在此定义），其作为化学因子受体活性调节剂是有用的。特别地，这些化合物作为化学因子受体CCR-5和/或CCR-3的调节剂是有用的。
• 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
  作者：Michael Palucki、Joann M. Um、Nobuyoshi Yasuda、David A. Conlon、Fuh-Rong Tsay、Frederick W. Hartner、Yi Hsiao、Benjamin Marcune、Sandor Karady、David L. Hughes、Peter G. Dormer、Paul J. Reider

  DOI：10.1021/jo025890a

  日期：2002.8.1

  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.