(S)-2-氯-6,7-二氢-5H-环戊[b]吡啶-7-醇 | 911405-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: (S)-2-氯-6,7-二氢-5H-环戊[b]吡啶-7-醇
• 英文名称: (S)-2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol
• 英文别名: 2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol；(7S)-2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol
• CAS: 911405-98-6
• 化学式: C₈H₈ClNO
• 分子量: 169.611
• InChiKey: XZVGQEYEEUNMQM-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-氯-6,7-二氢-5H-环戊[b]吡啶-7-醇 在 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 四丁基碘化铵 、 sodium hydride 、 三氟乙酸 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (7S)-7-[(3-fluorobenzyl)oxy]-2-[(2R)-2-methylpiperazin-1-yl]-6,7-dihydro-5H-cyclopenta[b]pyridine
  参考文献：
  名称：

  WO2006/103511

  摘要：

  公开号：
• 作为产物：
  描述：

  7(S) 2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 以98%的产率得到(S)-2-氯-6,7-二氢-5H-环戊[b]吡啶-7-醇
  参考文献：
  名称：

  Design and synthesis of orally-active and selective azaindane 5HT2c agonist for the treatment of obesity

  摘要：

  Based on our original pyrazine hit, CP-0809101, novel conformationally-restricted 5HT2c receptor agonists with 2-piperazin-azaindane scaffold were designed. Synthesis and structure-activity relationship (SAR) studies are described with emphasis on optimization of the selectivity against 5HT2a and 5HT2b receptors with excellent 2c potency. Orally-active and selective compounds were identified with dose responsive in vivo efficacy in our pre-clinical food intake model. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.112

文献信息

• Preparative access to medicinal chemistry related chiral alcohols using carbonyl reductase technology
  作者：Andrew S. Rowan、Thomas S. Moody、Roger M. Howard、Toby J. Underwood、Iain R. Miskelly、Yanan He、Bo Wang

  DOI：10.1016/j.tetasy.2013.09.015

  日期：2013.11

  Libraries of highly enantioenriched secondary alcohols in both enantiomeric forms were synthesised by enzymatic reduction of their parent ketones using selectAZyme (TM) carbonyl reductase (CRED) technology. Commercially available CREDs were able to reduce a range of substrate classes efficiently and with very high enantioselectivity. Matching substrate classes to small subsets of CREDs enabled the fast development of preparative bioreductions and the rapid generation of 100-1500 mg samples of chiral alcohols in typically >95% ee and the majority in >= 99.0% ee. The conditions for small scale synthesis were then scaled up to 0.5 kg to deliver one of the chiral alcohols, (S)-1-(4-bromophenyl)-2-chloroethanol, in 99.8% ee and 91% isolated yield. (C) 2013 Elsevier Ltd. All rights reserved.