N-p-chlorophenyl-4-oxo-4-phenylbutanamide | 38752-55-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-p-chlorophenyl-4-oxo-4-phenylbutanamide
• 英文别名: N-(4-Chlorophenyl)-I(3)-oxobenzenebutanamide；N-(4-chlorophenyl)-4-oxo-4-phenylbutanamide
• CAS: 38752-55-5
• 化学式: C₁₆H₁₄ClNO₂
• 分子量: 287.746
• InChiKey: CYMBDUYXALRMMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-p-chlorophenyl-4-oxo-4-phenylbutanamide 在 五氯化磷 、 叠氮基三甲基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 18.25h， 生成 C₁₆H₁₃ClN₄O
  参考文献：
  名称：

  Modulation of 11β-hydroxysteroid dehydrogenase type 1 activity by 1,5-substituted 1H-tetrazoles

  摘要：

  Inhibitors of 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD1) show promise as drugs to treat metabolic disease and CNS disorders such as cognitive impairment. A series of 1,5-substituted 1H-tetrazole 11 beta-HSD1 inhibitors has been discovered and chemically modified. Compounds are selective for 11 beta-HSD1 over 11 beta-HSD2 and possess good cellular potency in human and murine 11 beta-HSD1 assays. A range of in vitro stabilities are observed in human liver microsome assays. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.055
• 作为产物：
  描述：

  对氯苯胺 、 3-苯丙烯溴酸酯 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 N-p-chlorophenyl-4-oxo-4-phenylbutanamide
  参考文献：
  名称：

  Modulation of 11β-hydroxysteroid dehydrogenase type 1 activity by 1,5-substituted 1H-tetrazoles

  摘要：

  Inhibitors of 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD1) show promise as drugs to treat metabolic disease and CNS disorders such as cognitive impairment. A series of 1,5-substituted 1H-tetrazole 11 beta-HSD1 inhibitors has been discovered and chemically modified. Compounds are selective for 11 beta-HSD1 over 11 beta-HSD2 and possess good cellular potency in human and murine 11 beta-HSD1 assays. A range of in vitro stabilities are observed in human liver microsome assays. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.055

文献信息

• Sulfur-Containing Heterocycles Derived by Reaction of ?-Keto Amides withLawesson's Reagent
  作者：Takehiko Nishio

  DOI：10.1002/hlca.19980810531

  日期：——

  The reaction of ω-keto amides with Lawesson's reagent (LR: 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide) is described. Treatment of 3-keto amides (2-acylacetamides) 1 with LR gave the corresponding 3-keto thioamides 2, along with 1,2-dithiole-3-thiones 3. Treatment of 4-keto amides, 3-acyl propionamides 5, with LR yielded five-membered heterocycles, pyrroles 6 and/or 2-aminothiophenes

  描述了ω-酮酰胺与Lawesson试剂（LR：2,4-双（4-甲氧基苯基）-1,3,2,4-二硫代二膦烷2,4-二硫键）的反应。用LR处理3-酮酰胺（2-酰基乙酰胺）1得到相应的3-酮硫酰胺2，以及1,2-二硫代-3-硫酮3。用LR处理4-酮酰胺，3-酰基丙酰胺5，得到五元杂环，吡咯6和/或2-氨基噻吩7。5-酮基酰胺，3-苯甲酰基丁酰胺8与LR反应生成二氢噻喃-2-硫酮9作为唯一产品​​，但收率低。2-酰基苯甲酰胺10也与LR反应，得到3-巯基异吲哚啉-2-酮11或二氢异苯并噻吩-1-硫酮12。
• Studies on 5-benzoyl-3-isothiazolinones
  作者：Roger J.S. Beer、David Wright

  DOI：10.1016/s0040-4020(01)98885-4

  日期：1981.1

  nones are obtained when β-benzoylpropionamides are heated with thionyl chloride. Some reactions of 5-benzoyl-2-phenyl-3-isothiazolinone are described, the most interesting being that with dimethyl and diethyl malonate carbanions, in which ring opening, loss of sulphur, and subsequent ring closure occur, leading to maleimide derivatives.

  当将β-苯甲酰基丙酰胺与亚硫酰氯一起加热时，可获得5-苄基-3-异噻唑啉酮。描述了5-苯甲酰基-2-苯基-3-异噻唑啉酮的一些反应，最令人感兴趣的是与丙二酸二甲酯和丙二酸二乙酯的碳负离子反应，其中发生开环，硫损失和随后的闭环，从而导致马来酰亚胺衍生物。
• Tsolomitis, A.; Sandris, C., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1645 - 1646
  作者：Tsolomitis, A.、Sandris, C.

  DOI：——

  日期：——
• TSOLOMITIS A.; SANDRIS C., J. HETEROCYCL. CHEM., 1980, 17, NO 7, 1645-1646
  作者：TSOLOMITIS A.、 SANDRIS C.

  DOI：——

  日期：——
• Modulation of 11β-hydroxysteroid dehydrogenase type 1 activity by 1,5-substituted 1H-tetrazoles
  作者：Scott P. Webster、Margaret Binnie、Kirsty M.M. McConnell、Karen Sooy、Peter Ward、Michael F. Greaney、Andy Vinter、T. David Pallin、Hazel J. Dyke、Matthew I.A. Gill、Ines Warner、Jonathan R. Seckl、Brian R. Walker

  DOI：10.1016/j.bmcl.2010.04.055

  日期：2010.6

  Inhibitors of 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD1) show promise as drugs to treat metabolic disease and CNS disorders such as cognitive impairment. A series of 1,5-substituted 1H-tetrazole 11 beta-HSD1 inhibitors has been discovered and chemically modified. Compounds are selective for 11 beta-HSD1 over 11 beta-HSD2 and possess good cellular potency in human and murine 11 beta-HSD1 assays. A range of in vitro stabilities are observed in human liver microsome assays. (C) 2010 Elsevier Ltd. All rights reserved.