[(S)-3-(3,4-Dichloro-phenyl)-3-(3-iodo-propyl)-piperidin-1-yl]-phenyl-methanone | 188916-67-8

• 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: [(S)-3-(3,4-Dichloro-phenyl)-3-(3-iodo-propyl)-piperidin-1-yl]-phenyl-methanone
• 英文别名: (S)-(3-(3,4-Dichlorophenyl)-3-(3-iodopropyl)piperidin-1-yl)(phenyl)methanone；[(3S)-3-(3,4-dichlorophenyl)-3-(3-iodopropyl)piperidin-1-yl]-phenylmethanone
• CAS: 188916-67-8
• 化学式: C₂₁H₂₂Cl₂INO
• 分子量: 502.222
• InChiKey: XFAAEZSRGNMTTA-NRFANRHFSA-N

物化性质

• 沸点：
  566.2±50.0 °C(Predicted)
• 密度：
  1.503

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  [(S)-3-(3,4-Dichloro-phenyl)-3-(3-iodo-propyl)-piperidin-1-yl]-phenyl-methanone 、 N-Methyl-N-(4-phenyl-piperidin-4-yl)-acetamide; hydrochloride 在 potassium hydrogencarbonate 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以88%的产率得到奥沙奈坦
  参考文献：
  名称：

  A practical and scalable synthesis of SR 142801, a tachykinin NK3 antagonist

  摘要：

  A practical and scalable total synthesis of tachykinin NK3 receptor antagonist SR 142801, (R)-N-[1-[3-[1-benzoyl-3-(3,4-dichlorophenyl)-3-piperidinyl]propyl]-4-phenyl-4-piperidinyl]-N-methyl acetamide 1 is described. The absolute configuration of the key intermediate 7 was determined by single crystal X-ray crystallography, on the basis of which, the absolute configuration of SR 142801 should be (R)-(+), instead of the recently reported (S)-(+).(1) (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00064-4
• 作为产物：
  描述：

  (S)-(3-(3,4-dichlorophenyl)-3-(3-hydroxypropyl)piperidin-1-yl)(phenyl)methanone 在 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 20.0h， 生成 [(S)-3-(3,4-Dichloro-phenyl)-3-(3-iodo-propyl)-piperidin-1-yl]-phenyl-methanone
  参考文献：
  名称：

  A practical and scalable synthesis of SR 142801, a tachykinin NK3 antagonist

  摘要：

  A practical and scalable total synthesis of tachykinin NK3 receptor antagonist SR 142801, (R)-N-[1-[3-[1-benzoyl-3-(3,4-dichlorophenyl)-3-piperidinyl]propyl]-4-phenyl-4-piperidinyl]-N-methyl acetamide 1 is described. The absolute configuration of the key intermediate 7 was determined by single crystal X-ray crystallography, on the basis of which, the absolute configuration of SR 142801 should be (R)-(+), instead of the recently reported (S)-(+).(1) (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00064-4

文献信息

• A practical and scalable synthesis of SR 142801, a tachykinin NK3 antagonist
  作者：Huai.G. Chen、F.-Z. Chung、O.P. Goel、D. Johnson、S. Kesten、J. Knobelsdorf、H.T. Lee、J.R. Rubin

  DOI：10.1016/s0960-894x(97)00064-4

  日期：1997.3

  A practical and scalable total synthesis of tachykinin NK3 receptor antagonist SR 142801, (R)-N-[1-[3-[1-benzoyl-3-(3,4-dichlorophenyl)-3-piperidinyl]propyl]-4-phenyl-4-piperidinyl]-N-methyl acetamide 1 is described. The absolute configuration of the key intermediate 7 was determined by single crystal X-ray crystallography, on the basis of which, the absolute configuration of SR 142801 should be (R)-(+), instead of the recently reported (S)-(+).(1) (C) 1997 Elsevier Science Ltd.