2-chloro-N-[(1S)-2,3-dihydro-1H-inden-1-yl]acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-chloro-N-[(1S)-2,3-dihydro-1H-inden-1-yl]acetamide
• 英文别名: 2-chloro-N-((1S)-indanyl)acetamide
• 化学式: C₁₁H₁₂ClNO
• mdl: MFCD12106366
• 分子量: 209.675
• InChiKey: PXOJBWMHNNIZLL-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloro-N-[(1S)-2,3-dihydro-1H-inden-1-yl]acetamide 、 (2R)-3-(2-methylbenzothiazol-5-yloxy)-1-piperazinylpropan-2-ol 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-{4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinyl}-N-((1S)indanyl)acetamide
  参考文献：
  名称：

  New fatty acid oxidation inhibitors with increased potency lacking adverse metabolic and electrophysiological properties

  摘要：

  New inhibitors of palmitoylCoA oxidation were synthesized based on a structurally novel lead, CVT-3501 (1). Investigation of structure-activity relationships was conducted with respect to potency of inhibition of cardiac mitochondrial palmitoylCoA oxidation and metabolic stability. Potent and metabolically stable analogues 33, 42, and 43 were evaluated in vitro for cytochrome P450 inhibition and potentially adverse electrophysiological effects. Compound 33 was also found to have favorable pharmacokinetic properties in rat. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.093
• 作为产物：
  描述：

  (S)-(+)-1-茚满基异氰酸酯 、 氯碘甲烷 在 甲基锂 、 lithium bromide 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以95%的产率得到2-chloro-N-[(1S)-2,3-dihydro-1H-inden-1-yl]acetamide
  参考文献：
  名称：

  Homologation of Isocyanates with Lithium Carbenoids: A Straightforward Access to α-Halomethyl- and α,α-Dihalomethylamides

  摘要：

  Treatment of widely available isocyanates with monohalolithium and dihalolithium carbenoids provides a valuable protocol for the one-pot preparation of -halo- and ,-dihaloacetamide derivatives. While monohalolithium carbenoids can be prepared by a smooth lithium-halogen exchange, the preparation of the corresponding dihalo compounds proved to be highly dependent on the base used to realize the deprotonation, with lithium 2,2,6,6-tetramethylpiperidine emerging as optimal. The clear advantages of the procedure are: (a) broad scope of isocyanates that can be employed; (b) preservation of the optical purity when chiral materials are used; (c) divergent access to different haloamides by simply selecting the homologating agents. We also report an application of Charette's imidoyl triflate activation of a secondary amide to the synthesis of an -chloro ketone and N-15 NMR data for selected compounds.

  DOI：

  10.1055/s-0034-1379209

文献信息

• Substituted heterocyclic compounds
  申请人：——

  公开号：US20040152890A1

  公开（公告）日：2004-08-05

  Disclosed are novel heterocyclic derivatives, useful for the treatment of various disease states, in particular cardiovascular diseases such as atrial and ventricular arrhythmias, intermittent claudication, Prinzmetal's (variant) angina, stable and unstable angina, exercise induced angina, congestive heart disease, and myocardial infarction. The compounds are also useful in the treatment of diabetes.

  本发明涉及新型杂环衍生物，可用于治疗各种疾病状态，特别是心血管疾病，如心房和心室心律失常、间歇性跛行、普林兹梅特尔（变异型）心绞痛、稳定和不稳定性心绞痛、运动诱发性心绞痛、充血性心力衰竭和心肌梗塞。该化合物也可用于糖尿病的治疗。
• Substituted piperazine compounds and their use as fatty acid oxidation inhibitors
  申请人：CV THERAPEUTICS, INC.

  公开号：EP1806346A1

  公开（公告）日：2007-07-11

  Disclosed are novel heterocyclic derivatives, useful for the treatment of various disease states, in particular cardiovascular diseases such as atrial and ventricular arrhythmias, intermittent claudication, Prinzmetal's (variant) angina, stable and unstable angina, exercise induced angina, congestive heart disease, and myocardial infarction. The compounds are also useful in the treatment of diabetes.

  所公开的新型杂环衍生物可用于治疗各种疾病，尤其是心血管疾病，如房性和室性心律失常、间歇性跛行、普林兹梅塔尔（变异型）心绞痛、稳定型和不稳定型心绞痛、运动诱发心绞痛、充血性心脏病和心肌梗塞。这些化合物还可用于治疗糖尿病。
• US7125876B2
  申请人：——

  公开号：US7125876B2

  公开（公告）日：2006-10-24
• US7407960B2
  申请人：——

  公开号：US7407960B2

  公开（公告）日：2008-08-05
• Homologation of Isocyanates with Lithium Carbenoids: A Straightforward Access to α-Halomethyl- and α,α-Dihalomethylamides
  作者：Vittorio Pace、Laura Castoldi、Ashenafi Mamuye、Wolfgang Holzer

  DOI：10.1055/s-0034-1379209

  日期：——

  Treatment of widely available isocyanates with monohalolithium and dihalolithium carbenoids provides a valuable protocol for the one-pot preparation of -halo- and ,-dihaloacetamide derivatives. While monohalolithium carbenoids can be prepared by a smooth lithium-halogen exchange, the preparation of the corresponding dihalo compounds proved to be highly dependent on the base used to realize the deprotonation, with lithium 2,2,6,6-tetramethylpiperidine emerging as optimal. The clear advantages of the procedure are: (a) broad scope of isocyanates that can be employed; (b) preservation of the optical purity when chiral materials are used; (c) divergent access to different haloamides by simply selecting the homologating agents. We also report an application of Charette's imidoyl triflate activation of a secondary amide to the synthesis of an -chloro ketone and N-15 NMR data for selected compounds.