methyl (5S)-5-(3-fluorophenyl)-3-oxo-6-heptenoate | 395065-67-5

• 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: methyl (5S)-5-(3-fluorophenyl)-3-oxo-6-heptenoate
• 英文别名: (S)-methyl 5-(3-fluorophenyl)-3-oxohept-6-enoate；methyl (5S)-5-(3-fluorophenyl)-3-oxohept-6-enoate
• CAS: 395065-67-5
• 化学式: C₁₄H₁₅FO₃
• 分子量: 250.27
• InChiKey: GWWYXANCZPTHBC-SNVBAGLBSA-N

物化性质

• 沸点：
  322.4±32.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 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 、 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 31.5h， 生成 methyl (5S)-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：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。
• Iridium-catalyzed direct asymmetric vinylogous allylic alkylation
  作者：Chang-Yun Shi、Jun-Zhao Xiao、Liang Yin

  DOI：10.1039/c8cc07249c

  日期：——

  alkylation of α,β-unsaturated lactones (including coumarins) was achieved with excellent regio- and enantioselectivity. Transformations of the product were carried out by means of the versatile terminal olefin and lactone moieties. The synthetic application of the present methodology was showcased by the asymmetric synthesis of an advanced synthetic Merck intermediate toward a new drug candidate.

  α，β-不饱和内酯（包括香豆素）的催化不对称乙烯基烯丙基烷基化反应具有出色的区域和对映选择性。借助通用的末端烯烃和内酯部分进行产物的转化。通过先进的合成默克中间体向新药物候选者的不对称合成，展示了本方法学的合成应用。
• 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.