(S)-(+)-5-(2-chloro-1-oxo)propyl-1,3-dihydro-3,3-dimethyl-2H-indol-2-one | 185199-35-3

• 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: (S)-(+)-5-(2-chloro-1-oxo)propyl-1,3-dihydro-3,3-dimethyl-2H-indol-2-one
• 英文别名: 5-[(2S)-2-chloropropanoyl]-3,3-dimethyl-1H-indol-2-one
• CAS: 185199-35-3
• 化学式: C₁₃H₁₄ClNO₂
• 分子量: 251.713
• InChiKey: IBEFIEYLTPBLBO-ZETCQYMHSA-N

物化性质

• 沸点：
  438.1±45.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(+)-5-(2-chloro-1-oxo)propyl-1,3-dihydro-3,3-dimethyl-2H-indol-2-one 在 sodium hydride 作用下， 以 neat (no solvent) 为溶剂， 反应 1.04h， 生成 3,3-Dimethyl-5-((R)-6-methyl-2-oxo-3,6-dihydro-2H-[1,3,4]thiadiazin-5-yl)-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Stereospecificity of myofibrillar calcium sensitivity and PDE inhibition in cardiotonic thiadiazinones

  摘要：

  In pyridazinone or thiadiazinone cardiotonic agents with one chiral centre, the PDE inhibitory action resides mainly in one enantiomer and the myofibrillar calcium sensitization mainly in the other. This phenomenon is observed when the chiral centre is located on the pyridazinone or thiadiazinone heterocycle, but cannot be extended to structures where the chiral centre is elsewhere on the molecule. For the first time a stereoselective synthesis of a 5-substituted 3,6-dihydro-6-methyl-2H-1,3,4-thiadiazine-2-one has been achieved and an absolute configuration is proposed.

  DOI：

  10.1016/0223-5234(96)83974-2
• 作为产物：
  描述：

  1,2-二氢-3,3-二甲基-2-氧代-3H-吲哚 、 2-氯丙酰氯 在 三氯化铝 、 N,N-二甲基甲酰胺 作用下， 以 neat (no solvent) 为溶剂， 反应 2.0h， 以50%的产率得到(S)-(+)-5-(2-chloro-1-oxo)propyl-1,3-dihydro-3,3-dimethyl-2H-indol-2-one
  参考文献：
  名称：

  Stereospecificity of myofibrillar calcium sensitivity and PDE inhibition in cardiotonic thiadiazinones

  摘要：

  In pyridazinone or thiadiazinone cardiotonic agents with one chiral centre, the PDE inhibitory action resides mainly in one enantiomer and the myofibrillar calcium sensitization mainly in the other. This phenomenon is observed when the chiral centre is located on the pyridazinone or thiadiazinone heterocycle, but cannot be extended to structures where the chiral centre is elsewhere on the molecule. For the first time a stereoselective synthesis of a 5-substituted 3,6-dihydro-6-methyl-2H-1,3,4-thiadiazine-2-one has been achieved and an absolute configuration is proposed.

  DOI：

  10.1016/0223-5234(96)83974-2

文献信息

• Stereospecificity of myofibrillar calcium sensitivity and PDE inhibition in cardiotonic thiadiazinones
  作者：G Nadler、I Delimoge、P Lahouratate、I Leger、M Morvan、RG Zimmermann

  DOI：10.1016/0223-5234(96)83974-2

  日期：1996.1

  In pyridazinone or thiadiazinone cardiotonic agents with one chiral centre, the PDE inhibitory action resides mainly in one enantiomer and the myofibrillar calcium sensitization mainly in the other. This phenomenon is observed when the chiral centre is located on the pyridazinone or thiadiazinone heterocycle, but cannot be extended to structures where the chiral centre is elsewhere on the molecule. For the first time a stereoselective synthesis of a 5-substituted 3,6-dihydro-6-methyl-2H-1,3,4-thiadiazine-2-one has been achieved and an absolute configuration is proposed.