2-bromo-5-phenylcyclohex-2-en-3-ol-1-one | 70336-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-5-phenylcyclohex-2-en-3-ol-1-one
• 英文别名: 2-bromo-3-hydroxy-5-phenylcyclohex-2-enone；2-Cyclohexen-1-one, 2-bromo-3-hydroxy-5-phenyl-；2-bromo-3-hydroxy-5-phenylcyclohex-2-en-1-one
• CAS: 70336-36-6
• 化学式: C₁₂H₁₁BrO₂
• 分子量: 267.122
• InChiKey: VVNFVIFXTSICIM-UHFFFAOYSA-N

物化性质

• 熔点：
  205 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  355.5±42.0 °C(Predicted)
• 密度：
  1.592±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-5-phenylcyclohex-2-en-3-ol-1-one 以13%的产率得到
  参考文献：
  名称：

  CHANDRASEKHARAN, V.;UNNIKRISHNAN, P.;SHAH, G. D.;BHATTACHARYYA, S. C., INDIAN J. CHEM., 1980, 19, N 12, 1052-1055

  摘要：

  DOI：
• 作为产物：
  描述：

  4-苯基-3-丁烯-2-醇 在 N-溴代丁二酰亚胺(NBS) 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 8.0h， 生成 2-bromo-5-phenylcyclohex-2-en-3-ol-1-one
  参考文献：
  名称：

  Identification of substituted 3-hydroxy-2-mercaptocyclohex-2-enones as potent inhibitors of human lactate dehydrogenase

  摘要：

  A novel class of 3-hydroxy-2-mercaptocyclohex-2-enone-containing inhibitors of human lactate dehydrogenase (LDH) was identified through a high-throughput screening approach. Biochemical and surface plasmon resonance experiments performed with a screening hit (LDHA IC50 = 1.7 mu M) indicated that the compound specifically associated with human LDHA in a manner that required simultaneous binding of the NADH co-factor. Structural variation of this screening hit resulted in significant improvements in LDHA biochemical inhibition activity (best IC50 = 0.18 mu M). Two crystal structures of optimized compounds bound to human LDHA were obtained and explained many of the observed structure-activity relationships. In addition, an optimized inhibitor exhibited good pharmacokinetic properties after oral administration to rats (F = 45%). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.06.076

文献信息

• A convenient and efficient preparation of β-substituted α-haloenones from diazodicarbonyl compounds
  作者：Yong Rok Lee、Bang Sub Cho、Hyuk Jin Kwon

  DOI：10.1016/j.tet.2003.09.087

  日期：2003.11

  Rhodium(II)-catalyzed reactions of cyclic diazodicarbonyl compounds with a variety of halides have been examined. With acid halides, β-acyloxy α-haloenones are produced in good yields. With benzyl halides, β-benzyloxy α-haloenones are obtained in good yields. Reactions with methylene halides yield β-halomethoxy α-haloenones in good yields, whereas reactions with ethyl halides and ethylene dihalides

  已经研究了铑（II）催化的环状重氮二羰基化合物与各种卤化物的反应。用酰基卤可以高收率生产β-酰氧基α-卤代烯酮。使用苄基卤化物，可以良好的产率获得β-苄氧基α-卤代烯酮。与亚甲基卤的反应以良好的产率产生β-卤代甲氧基α-卤代烯酮，而与乙基卤和乙二卤的反应以高产率产生β-羟基α-卤代烯。这些反应提供了有用且快速的进入β-取代的α-卤代烯酮的途径。还已经用卤化pathway描述了形成这些产物的机理途径。
• Dihydrobenzoimidazothiazoles as novel anti-infective agents: Synthesis, biological evaluation and docking studies
  作者：Rakesh Kumar Bollikanda、Naga Pranathi Abburi、Devendra Nagineni、Nagaraju Chirra、Pavan Kumar Bangalore、Sunil Misra、Balasubramanian Sridhar、Srinivas Kantevari

  DOI：10.1016/j.molstruc.2023.137315

  日期：2024.3

  Benzoimidazothiazole are a novel class of small molecules that have not been studied on a variety of pharmacological targets. In this report, we discussed novel dihydrobenzo-imidazothiazole scaffold as promising anti-infective agents. Commercially available 1,3-cyclohexane-diones (1a–h) were brominated before being condensed with thiourea to produce 2-amino-5,6-dihydrobenzo[d]thiazol-7(4H)-ones (3a–h) in excellent yields

  鉴于传染病威胁日益严重，迫切需要寻找更安全、更强大和更有效的分子。苯并咪唑并噻唑是一类新型小分子，尚未针对多种药理学靶点进行研究。在本报告中，我们讨论了新型二氢苯并咪唑噻唑支架作为有前途的抗感染剂。将市售的 1,3-环己烷-二酮 (1a–h) 进行溴化，然后与硫脲缩合，以优异的性能生产 2-氨基-5,6-二氢苯并[d]噻唑-7(4H)-酮 (3a–h)。产量。化合物3a-h与2-溴-1-(5-氯噻吩-2-基)乙烷-1-酮(4)环化，生成2-(5-氯噻吩-2-基)-6,7-二氢苯并[ d]咪唑并[2,1-b]噻唑-8(5H)-酮(5a-h)。当检查合成类似物 3a-h 和 5a-h 的生物活性时，它们对测试的抗病毒和抗菌菌株表现出有效的抑制作用。两种类似物，3 小时（CC 50 ：>300 µM，IC 50 = 8.3 µM，SI = >36）和 5 小时（CC 50 ：>300 µM ，IC
• Chandrasekharan,V. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1978, vol. 16, p. 970 - 972
  作者：Chandrasekharan,V. et al.

  DOI：——

  日期：——
• Chandrasekharan, V.; Unnikrishnan, P.; Shah, G. D., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 12, p. 1052 - 1055
  作者：Chandrasekharan, V.、Unnikrishnan, P.、Shah, G. D.、Bhattacharyya, S. C.

  DOI：——

  日期：——