5-(3-methoxyphenyl)-2,3-dihydro-1H-inden-1-one | 863479-23-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-(3-methoxyphenyl)-2,3-dihydro-1H-inden-1-one
• 英文别名: 5-(3-methoxyphenyl)-2,3-dihydroinden-1-one
• CAS: 863479-23-6
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: IQCUZEBHRQHSAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(3-methoxyphenyl)-2,3-dihydro-1H-inden-1-one 在 咪唑 、 三乙基硅烷 、 六甲基磷酰三胺 、 四氧化锇 、 phosphate buffer 、 三氟化硼乙醚 、 水 、 sodium hydride 、 N-甲基吗啉氧化物 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 生成 2-[(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-(3-methoxy-phenyl)-indan-1-yl]-2-methyl-6-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-hexanoic acid ethyl ester
  参考文献：
  名称：

  Synthetic [5,5] trans-fused indane lactones as inhibitors of thrombin

  摘要：

  Synthesis of trans-fused lactones containing; the indane nucleus has resulted in a series of potent acylating inhibitors of thrombin. As an er;ample compound Ile has an apparent second order rate constant of 11x10(6) M(-1)sec(-1) for the inhibition of thrombin. The anticoagulant activity of these compounds is discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00002-5
• 作为产物：
  描述：

  5-溴茚酮 、 3-甲氧基苯硼酸 在 palladium diacetate 、 四丁基溴化铵 、 potassium carbonate 作用下， 以72%的产率得到5-(3-methoxyphenyl)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  6-Aryl-8H-indeno[1,2-d]thiazol-2-ylamines:  A₁ Adenosine Receptor Agonist Allosteric Enhancers Having Improved Potency

  摘要：

  Allosteric enhancers (AEs) of the A(1) adenosine receptor (A(1)AR) have potential as drugs for treating neurological, cardiovascular, and renal diseases. This report describes the synthesis and evaluation of a series of 6-aryl-8H-indeno[1,2-d]thiazol-2-ylamines that exhibited AE activity at the A(1)AR. Palladium-mediated condensation of arylboronic acids with 5-bromoindan-1-one generated arylindanones 2a-aj for iodine-catalyzed condensation with thiourea, generating 2-aminothiazolium salts 3a-aj. Binding studies using membranes from cells stably expressing human A(1)ARs, A(2A)ARs, or A(3)ARs evaluated AE activity and receptor subtype selectivity. The EC50 of the AE activities of compounds 3m-o, 3x, and 3ae were 2.2, 1.5, 0.9, 1.0, and 3.0,mu M, respectively, substantially lower than that of the well characterized 2-amino3-aroylthiophene (PD 81,723), > 10 mu M. The new compounds also have substantially higher maximal AE activity. These compounds had no AE activity at the A(2A)AR and only minimal activity at the A(3)AR.

  DOI：

  10.1021/jm049132j

文献信息

• One-step highly selective borylation/Suzuki cross-coupling of two distinct aryl bromides in pure water
  作者：Shan Dong Xu、Fang Zhou Sun、Wei Hang Deng、Han Hao、Xin Hong Duan

  DOI：10.1039/c8nj02184h

  日期：——

  A Na2PdCl4-catalysed B2(OH)4-mediated direct cross-coupling of two distinct aryl bromides in pure water is described. This one-step borylation/Suzuki method exhibits an outstanding cross-coupling selectivity and no tendency to produce homocoupling products, therefore leading to biaryls and heterobiaryls in moderate to good yields. Moreover, the reaction has high regio-selectivity and can be scaled-up

  描述了Na 2 PdCl 4催化的B 2（OH）4介导的两种不同的芳基溴化物在纯水中的直接交叉偶联。这种一步式硼化/铃木法显示出优异的交叉偶联选择性，并且没有产生均偶联产物的趋势，因此导致联芳基和杂联芳基的产率中等至良好。而且，该反应具有高的区域选择性并且可以扩大规模。使用这种简单，经济和实用的方案，可以实现3,5-二溴吡啶的不对称二芳基化。
• 2-Aminothiazole allosteric enhancers of a ?1? adenosine receptors
  申请人：Linden Joel

  公开号：US20050027125A1

  公开（公告）日：2005-02-03

  The present invention relates generally to a class of 2-aminothiazole derivatives which have recently been identified as allosteric enhancers of the A 1? adenosine receptor. These compounds, and therapeutic compositions containing them, are useful for treating conditions in which activation of the A 1? adenosine receptor would be beneficial, for example, those conditions in which stimulation of angiogenesis would improve blood flow to ischemic tissues.

  本发明总体上涉及一类 2-氨基噻唑衍生物，这些衍生物最近被鉴定为 A 1?这些化合物以及含有它们的治疗组合物可用于治疗激活 A 1? 1? 腺苷受体将是有益的，例如，刺激血管生成将改善缺血组织的血流量。
• EP1583530A4
  申请人：——

  公开号：EP1583530A4

  公开（公告）日：2008-07-23
• 2-AMINOTHIAZOLE ALLOSTERIC ENHANCERS OF A1-ADENOSINE RECEPTORS
  申请人：UNIVERSITY OF VIRGINIA PATENT FOUNDATION

  公开号：EP1583530A1

  公开（公告）日：2005-10-12
• US7485655B2
  申请人：——

  公开号：US7485655B2

  公开（公告）日：2009-02-03