(S)-(+)-1-(benzofuran-2-yl)-2-chloroethanol | 556026-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (S)-(+)-1-(benzofuran-2-yl)-2-chloroethanol
• 英文别名: (S)-2-(1-hydroxy-2-chloroethyl)-benzofuran；S-1-(2-benzofuranyl)-2-chloroethanol；(1S)-1-(1-benzofuran-2-yl)-2-chloroethan-1-ol；(1S)-1-(1-benzofuran-2-yl)-2-chloroethanol
• CAS: 556026-00-7
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: CDHCVIVEPPHYOH-MRVPVSSYSA-N

物化性质

• 沸点：
  324.3±27.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(+)-1-(benzofuran-2-yl)-2-chloroethanol 在 氢氧化钾 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.25h， 生成 (R)-1-(benzofuran-2-yl)-2-(methylamino)ethanol
  参考文献：
  名称：

  Solvent and in situ catalyst preparation impacts upon Noyori reductions of aryl-chloromethyl ketones: application to syntheses of chiral 2-amino-1-aryl-ethanols

  摘要：

  As part of medicinal chemistry efforts we found it necessary to develop general syntheses of highly enantiomerically enriched 1-aryl-2-chloroethanols and 1-aryl-2-methylaminoethanols. A survey of literature methods suggested that a truly general approach had not yet been reported, encouraging us to undertake the development of such a methodology. This study describes the design, development, and reduction to practice of a general synthesis of chiral 1-aryl-2-chloroethanols and the transformation of these entities to highly enantiomerically enriched 1-aryl-2-methylaminoethanols. Of particular importance were observations of the impact of solvent and the method of catalyst preparation on the yield and enantiomerical excess of chlorohydrins prepared via Noyori transfer hydrogenations of aryl-chloromethyl ketones. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.017
• 作为产物：
  描述：

  2-[1-tri-isopropylsilyloxy-vinyl]-benzofuran 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 (1R,2R)-(-)-N-(对甲基苯磺酰基)-1,2-二苯基乙二胺 N-氯代丁二酰亚胺 、 甲酸 、 氢氟酸 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.5h， 生成 (S)-(+)-1-(benzofuran-2-yl)-2-chloroethanol
  参考文献：
  名称：

  Solvent and in situ catalyst preparation impacts upon Noyori reductions of aryl-chloromethyl ketones: application to syntheses of chiral 2-amino-1-aryl-ethanols

  摘要：

  As part of medicinal chemistry efforts we found it necessary to develop general syntheses of highly enantiomerically enriched 1-aryl-2-chloroethanols and 1-aryl-2-methylaminoethanols. A survey of literature methods suggested that a truly general approach had not yet been reported, encouraging us to undertake the development of such a methodology. This study describes the design, development, and reduction to practice of a general synthesis of chiral 1-aryl-2-chloroethanols and the transformation of these entities to highly enantiomerically enriched 1-aryl-2-methylaminoethanols. Of particular importance were observations of the impact of solvent and the method of catalyst preparation on the yield and enantiomerical excess of chlorohydrins prepared via Noyori transfer hydrogenations of aryl-chloromethyl ketones. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.017

文献信息

• Pyridoquinoxaline antivirals
  申请人：——

  公开号：US20030207877A1

  公开（公告）日：2003-11-06

  The present invention provides a compound of formula I 1 or a pharmaceutically acceptable salt thereof wherein R 1 , R 2 and R 3 are as defined in the specification. The compounds are useful for the treatment of viral infections.

  本发明提供了一种具有以下结构的化合物I或其药学上可接受的盐，其中R1、R2和R3如规范中定义。这些化合物对于治疗病毒感染是有用的。
• Enantioselective reduction of benzofuryl halomethyl ketones: asymmetric synthesis of (R)-bufuralol
  作者：Marek Zaidlewicz、Agnieszka Tafelska-Kaczmarek、Andrzej Prewysz-Kwinto

  DOI：10.1016/j.tetasy.2005.08.012

  日期：2005.10

  Enantioselective reduction of representative 2-(bromoacetyl)- and 2-(chloroacetyl)benzofurans with (-)-B-chloro-diisopinocampheylborane and by transfer hydrogenation with formic acid/triethylamine in the presence of RhCl[R,R-TsD-PEN](C5Me5) is described. Transfer hydrogenation of the chloro ketones produced the corresponding chlorohydrins of >= 95% ee. (R)-Bufuralol of 96% ce was prepared from the corresponding chloro ketone by transfer hydrogenation-substitution. (c) 2005 Elsevier Ltd. All rights reserved.
• PYRIDOQUINOXALINE ANTIVIRALS
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP1458719A1

  公开（公告）日：2004-09-22
• [EN] PYRIDOQUINOXALINE ANTIVIRALS<br/>[FR] ANTIVIRAUX A BASE DE PYRIDOQUINOXALINE
  申请人：UPJOHN CO

  公开号：WO2003053971A1

  公开（公告）日：2003-07-03

  The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof wherein R?1, R2 and R3¿ are as defined in the specification. The compounds are useful for the treatment of viral infections.