2-chloro-1-(indolin-1-yl)pent-4-en-1-one | 1239488-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-chloro-1-(indolin-1-yl)pent-4-en-1-one
• 英文别名: 2-Chloro-1-(2,3-dihydroindol-1-yl)pent-4-en-1-one
• CAS: 1239488-04-0
• 化学式: C₁₃H₁₄ClNO
• 分子量: 235.713
• InChiKey: WWROPWLLMIKRFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloro-1-(indolin-1-yl)pent-4-en-1-one 、 9-phenyl-9-borabicyclo[3.3.1]nonane 在 异丁醇 、 nickel(II) chloride2-methoxyethyl ether 、 potassium tert-butylate 、 (1S,2S)-(-)-N,N′-二甲基-1,2-双[3-(三氟甲基)苯基]-1,2-乙二胺 作用下， 以 甲苯 为溶剂， 以83%的产率得到1-(indolin-1-yl)-2-phenylpent-4-en-1-one
  参考文献：
  名称：

  Asymmetric Suzuki Cross-Couplings of Activated Secondary Alkyl Electrophiles: Arylations of Racemic α-Chloroamides

  摘要：

  A nickel-catalyzed stereoconvergent method for the enantioselective Suzuki arylation of racemic alpha-chloroamides has been developed. This process provides a unique example of an asymmetric arylation of an alpha-haloamide, an enantioselective arylation of an alpha-chlorocarbonyl compound, and an asymmetric Suzuki reaction with an activated alkyl electrophile or an arylboron reagent. The method is also applicable to the corresponding enantioselective cross-coupling of alpha-bromoamides. The coupling products can be transformed without racemization into enantio-enriched alpha-arylcarboxylic acids and primary alcohols. A modest kinetic resolution of the alpha-chloroamide was observed; a mechanistic study indicated that the selectivity may reflect discrimination by the chiral catalyst of the two enantiomeric alpha-chloroamides in an irreversible oxidative-addition process.

  DOI：

  10.1021/ja105148g
• 作为产物：
  描述：

  吲哚啉 、 2-chloro-4-pentenoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 以31%的产率得到2-chloro-1-(indolin-1-yl)pent-4-en-1-one
  参考文献：
  名称：

  Asymmetric Suzuki Cross-Couplings of Activated Secondary Alkyl Electrophiles: Arylations of Racemic α-Chloroamides

  摘要：

  A nickel-catalyzed stereoconvergent method for the enantioselective Suzuki arylation of racemic alpha-chloroamides has been developed. This process provides a unique example of an asymmetric arylation of an alpha-haloamide, an enantioselective arylation of an alpha-chlorocarbonyl compound, and an asymmetric Suzuki reaction with an activated alkyl electrophile or an arylboron reagent. The method is also applicable to the corresponding enantioselective cross-coupling of alpha-bromoamides. The coupling products can be transformed without racemization into enantio-enriched alpha-arylcarboxylic acids and primary alcohols. A modest kinetic resolution of the alpha-chloroamide was observed; a mechanistic study indicated that the selectivity may reflect discrimination by the chiral catalyst of the two enantiomeric alpha-chloroamides in an irreversible oxidative-addition process.

  DOI：

  10.1021/ja105148g

文献信息

• Asymmetric Suzuki Cross-Couplings of Activated Secondary Alkyl Electrophiles: Arylations of Racemic α-Chloroamides
  作者：Pamela M. Lundin、Gregory C. Fu

  DOI：10.1021/ja105148g

  日期：2010.8.18

  A nickel-catalyzed stereoconvergent method for the enantioselective Suzuki arylation of racemic alpha-chloroamides has been developed. This process provides a unique example of an asymmetric arylation of an alpha-haloamide, an enantioselective arylation of an alpha-chlorocarbonyl compound, and an asymmetric Suzuki reaction with an activated alkyl electrophile or an arylboron reagent. The method is also applicable to the corresponding enantioselective cross-coupling of alpha-bromoamides. The coupling products can be transformed without racemization into enantio-enriched alpha-arylcarboxylic acids and primary alcohols. A modest kinetic resolution of the alpha-chloroamide was observed; a mechanistic study indicated that the selectivity may reflect discrimination by the chiral catalyst of the two enantiomeric alpha-chloroamides in an irreversible oxidative-addition process.