2-chloro-1-(indolin-1-yl)propan-1-one | 1256601-02-1

• 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)propan-1-one
• 英文别名: (2R)-2-chloro-1-(2,3-dihydroindol-1-yl)propan-1-one
• CAS: 1256601-02-1
• 化学式: C₁₁H₁₂ClNO
• 分子量: 209.675
• InChiKey: DLXVQAFCFXWGFM-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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)propan-1-one 、 9-phenyl-9-borabicyclo[3.3.1]nonane 在 异丁醇 、 十四烷 、 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， 生成 (R)-1-(indolin-1-yl)-2-phenylpropan-1-one 、 (S)-1-(indolin-1-yl)-2-phenylpropan-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：

  9-phenyl-9-borabicyclo[3.3.1]nonane 、 (9ci)-1-(2-氯-1-氧代丙基)-2,3-二氢-1H-吲哚 在 异丁醇 、 十四烷 、 nickel(II) chloride2-methoxyethyl ether 、 potassium tert-butylate 、 (1R,2R)-(+)-N,N-二甲基-1,2-双[3-(三氟醚甲基)苯-1,2-乙烷二胺 作用下， 以 甲苯 为溶剂， 生成 2-chloro-1-(indolin-1-yl)propan-1-one 、 2-chloro-1-(indolin-1-yl)propan-1-one 、 (R)-1-(indolin-1-yl)-2-phenylpropan-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

• Pd-Catalyzed C–O Bond Formation Enabling the Synthesis of Congested <i>N</i>,<i>N</i>,<i>O</i>-Trisubstituted Hydroxylamines
  作者：Jiaxing Chen、Yongzhuo Xu、Wen Shao、Jianhua Ji、Boqiang Wang、Muyang Yang、Guojiang Mao、Fuhong Xiao、Guo-Jun Deng

  DOI：10.1021/acs.orglett.2c02975

  日期：2022.11.18

  A Pd-catalyzed C–O cross-coupling of O-acyl hydroxylamines and tertiary or secondary alkyl electrophiles was reported without the cleavage of the rather fragile N–O bond. The described strategy provides direct access to congested N,N,O-trisubstituted hydroxylamines bearing an α-quaternary carbon center under mild conditions in high yields and features exclusively chemoselective C–O bond formation,

  据报道，Pd 催化的O-酰基羟胺和叔或仲烷基亲电子试剂的 C-O 交叉偶联没有裂解相当脆弱的 N-O 键。所描述的策略提供了在温和条件下以高产率直接获得带有α-季碳中心的拥挤的 N、N、O-三取代羟胺，并具有独特的化学选择性 C-O 键形成、广泛的底物范围和出色的官能团耐受性。交叉偶联的合成潜力是通过药物衍生化和一系列催化后修饰建立的。
• 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.