(S)-Dichloroisoproterenol | 20879-18-9

• 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)-Dichloroisoproterenol
• 英文别名: (+)-Dichloroisoproterenol；(S)-2-Isopropylamino-1-(3,4-dichlorophenyl)ethanol；(1S)-1-(3,4-dichlorophenyl)-2-(propan-2-ylamino)ethanol
• CAS: 20879-18-9
• 化学式: C₁₁H₁₅Cl₂NO
• 分子量: 248.152
• InChiKey: VKMGSWIFEHZQRS-LLVKDONJSA-N

物化性质

• 沸点：
  361.0±37.0 °C(Predicted)
• 密度：
  1.221±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-Dichloroisoproterenol 在 盐酸 、 N-羟基-7-氮杂苯并三氮唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(4-{3-[(S)-2-(3,4-Dichloro-phenyl)-2-hydroxy-ethyl]-3-isopropyl-ureido}-phenyl)-2,2-dimethyl-propionamide
  参考文献：
  名称：

  Discovery and initial structure–Activity relationships of trisubstituted ureas as thrombin receptor (PAR-1) antagonists

  摘要：

  Thrombin is the most potent agonist of platelet activation, and its effects are predominantly mediated by platelet thrombin receptors. Therefore, antagonists of the thrombin receptor have potential utility for the treatment of thrombotic disorders. Screening of combinatorial libraries revealed 2 to be a potent antagonist of the thrombin receptor. Modifications of this structure produced 11k, which inhibits thrombin receptor stimulated secretion and aggregation of platelets. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00538-8
• 作为产物：
  描述：

  2-溴-3',4'-二氯苯乙酮 在 dimethyl sulfide borane 、 C₆H₁₄BNO₂ 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 19.5h， 生成 (S)-Dichloroisoproterenol
  参考文献：
  名称：

  β-肾上腺素能阻滞剂的不对称合成涉及原位手性有机催化剂形成的多步一锅法转化

  摘要：

  两只鸟一块石头：公开了一种用于对映选择性手性药物合成的新的原子经济单罐方法，该方法涉及原位多步有机催化剂的形成以及该反应在β-肾上腺素能阻滞剂多步序贯合成中的应用（参见方案）。

  DOI：

  10.1002/chem.201102931

文献信息

• One-pot route to β-adrenergic blockers via enantioselective organocatalysed epoxidation of terminal alkenes as a key step
  作者：Felix E. Held、Shengwei Wei、Kathrin Eder、Svetlana B. Tsogoeva

  DOI：10.1039/c4ra04011b

  日期：——

  A convenient and environmentally attractive one-pot two-step process for the synthesis of β-adrenergic blockers via Shi's organocatalytic epoxidation of terminal alkenes and subsequent aminolysis reaction of epoxides with isopropylamine under mild reaction conditions has been developed.

  开发了一种方便且环境友好的两步一锅法合成β-肾上腺素阻断剂的过程，该过程通过Shi的末端烯烃有机催化环氧化反应，随后在温和反应条件下利用异丙胺进行环氧化物的氨基解反应实现。
• A Two-Step Asymmetric Synthesis of (R)-Monoaryl Epoxides Using a Chiral Oxathiane as a Recoverable Reagent: Application to the Preparation of (R)-.beta.-Adrenergic Compounds
  作者：Arlette Solladie-Cavallo、Anh Diep-Vohuule

  DOI：10.1021/jo00116a041

  日期：1995.6

  It is shown that chiral oxathiane 1 is a recoverable and efficient chiral auxiliary which provides, in two steps, (R)-monoaryl epoxides in high enantiomeric purity (98% R and 92% R according to the solvent used). (R)-beta-Adrenergic compounds (R)-(-)-DCI and (R)-(-)-pronethalol call then be obtained from a regioselective opening of the corresponding epoxides using the reagent LiAl(NHR)(4)/NH(2)R.
• .beta.-Adrenergic blocking agents. III. The optical isomers of pronethalol, propranolol, and several related compounds
  作者：Ralph Howe、B. S. Rao

  DOI：10.1021/jm00312a003

  日期：1968.11
• Asymmetric Synthesis of β-Adrenergic Blockers through Multistep One-Pot Transformations Involving In Situ Chiral Organocatalyst Formation
  作者：Shengwei Wei、Regina Messerer、Svetlana B. Tsogoeva

  DOI：10.1002/chem.201102931

  日期：2011.12.16

  Two birds one stone: A new atom‐economical one‐pot approach to enantioselective chiral drug synthesis, involving in situ multistep organocatalyst formation and the application of the reaction for multistep sequential synthesis of β‐adrenergic blockers is disclosed (see scheme).

  两只鸟一块石头：公开了一种用于对映选择性手性药物合成的新的原子经济单罐方法，该方法涉及原位多步有机催化剂的形成以及该反应在β-肾上腺素能阻滞剂多步序贯合成中的应用（参见方案）。
• Discovery and initial structure–Activity relationships of trisubstituted ureas as thrombin receptor (PAR-1) antagonists
  作者：James C Barrow、Philippe G Nantermet、Harold G Selnick、Kristen L Glass、Phung L Ngo、Mary Beth Young、Janetta M Pellicore、Michael J Breslin、John H Hutchinson、Roger M Freidinger、Cindra Condra、Jerzy Karczewski、Rodney A Bednar、Stanley L Gaul、Andrew Stern、Robert Gould、Thomas M Connolly

  DOI：10.1016/s0960-894x(01)00538-8

  日期：2001.10

  Thrombin is the most potent agonist of platelet activation, and its effects are predominantly mediated by platelet thrombin receptors. Therefore, antagonists of the thrombin receptor have potential utility for the treatment of thrombotic disorders. Screening of combinatorial libraries revealed 2 to be a potent antagonist of the thrombin receptor. Modifications of this structure produced 11k, which inhibits thrombin receptor stimulated secretion and aggregation of platelets. (C) 2001 Elsevier Science Ltd. All rights reserved.