1-(3-chlorophenyl)-4-(4-methylphenyl)-1,4-butanedione | 364045-32-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-chlorophenyl)-4-(4-methylphenyl)-1,4-butanedione
• 英文别名: 1-(3-Chlorophenyl)-4-(4-methylphenyl)butane-1,4-dione；1-(3-chlorophenyl)-4-(4-methylphenyl)butane-1,4-dione
• CAS: 364045-32-9
• 化学式: C₁₇H₁₅ClO₂
• 分子量: 286.758
• InChiKey: AKOIJBYJVOIFQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  聚甘氨酸 、 1-(3-chlorophenyl)-4-(4-methylphenyl)-1,4-butanedione 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  Acylguanidine inhibitors of β-secretase: Optimization of the pyrrole ring substituents extending into the S1 and S3 substrate binding pockets

  摘要：

  Proteolytic cleavage of amyloid precursor protein by beta-secretase (BACE-1) and gamma-secretase leads to formation of beta-amyloid (A beta) a key component of amyloid plaques, which are considered the hallmark of Alzheimer's disease. Small molecule inhibitors of BACE-1 may reduce levels of A beta and thus have therapeutic potential for treating Alzheimer's disease. We recently reported the identification of a novel small molecule BACE-1 inhibitor N-[2-(2,5-diphenyl-pyrrol-1-yl)-acetyl]guanidine (3.a.1). We report here the initial hit-to-lead optimization of this hit and the SAR around the aryl groups occupying the S-1 and S-2' pockets leading to submicromolar BACE-1 inhibitors. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.010
• 作为产物：
  描述：

  4-(3-chlorophenyl)-4-cyano-4-morpholino-N-methoxy-N-methylbutyramide 在 copper(II) sulfate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 9.5h， 生成 1-(3-chlorophenyl)-4-(4-methylphenyl)-1,4-butanedione
  参考文献：
  名称：

  N-甲氧基-N-甲基-3-溴丙酰胺：一种新的三碳同系剂，用于合成不对称的1,4-二酮

  摘要：

  开发了一种基于α-氨基腈三碳同系物的合成路线，用于合成不对称的1,4-二酮。关键步骤是用N-甲氧基-N-甲基-3-溴丙酰胺对各种芳基和杂芳基α-氨基腈进行烷基化，然后将Grignard试剂添加到烷基化产物中，然后进行水解。

  DOI：

  10.1016/s0040-4020(01)00571-3

文献信息

• Acylguanidine inhibitors of β-secretase: Optimization of the pyrrole ring substituents extending into the S1 and S3 substrate binding pockets
  作者：Derek C. Cole、Joseph R. Stock、Rajiv Chopra、Rebecca Cowling、John W. Ellingboe、Kristi Y. Fan、Boyd L. Harrison、Yun Hu、Steve Jacobsen、Lee D. Jennings、Guixian Jin、Peter A. Lohse、Michael S. Malamas、Eric S. Manas、William J. Moore、Mary-Margaret O’Donnell、Andrea M. Olland、Albert J. Robichaud、Kristine Svenson、JunJun Wu、Eric Wagner、Jonathan Bard

  DOI：10.1016/j.bmcl.2007.12.010

  日期：2008.2

  Proteolytic cleavage of amyloid precursor protein by beta-secretase (BACE-1) and gamma-secretase leads to formation of beta-amyloid (A beta) a key component of amyloid plaques, which are considered the hallmark of Alzheimer's disease. Small molecule inhibitors of BACE-1 may reduce levels of A beta and thus have therapeutic potential for treating Alzheimer's disease. We recently reported the identification of a novel small molecule BACE-1 inhibitor N-[2-(2,5-diphenyl-pyrrol-1-yl)-acetyl]guanidine (3.a.1). We report here the initial hit-to-lead optimization of this hit and the SAR around the aryl groups occupying the S-1 and S-2' pockets leading to submicromolar BACE-1 inhibitors. (C) 2007 Elsevier Ltd. All rights reserved.
• N-Methoxy-N-methyl-3-bromopropionamide: a new three carbon homologating agent for the synthesis of unsymmetrical 1,4-diketones
  作者：V Selvamurugan、I.S Aidhen

  DOI：10.1016/s0040-4020(01)00571-3

  日期：2001.7

  A synthetic route based on a three carbon homologation of an α-aminonitrile was developed for the synthesis of unsymmetrical 1,4-diketones. The key steps were the alkylation of various aryl and heteroaryl α-aminonitriles with N-methoxy-N-methyl-3-bromopropionamide followed by the addition of a Grignard reagent to the alkylated product and then subsequent hydrolysis.

  开发了一种基于α-氨基腈三碳同系物的合成路线，用于合成不对称的1,4-二酮。关键步骤是用N-甲氧基-N-甲基-3-溴丙酰胺对各种芳基和杂芳基α-氨基腈进行烷基化，然后将Grignard试剂添加到烷基化产物中，然后进行水解。