2-(4-chloro-phenyl)-3-oxo-hexanenitrile | 855910-37-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-chloro-phenyl)-3-oxo-hexanenitrile
• 英文别名: 2-(4-Chlor-phenyl)-3-oxo-hexannitril；2-(4-Chlorophenyl)-3-oxohexanenitrile
• CAS: 855910-37-1
• 化学式: C₁₂H₁₂ClNO
• 分子量: 221.686
• InChiKey: RWHAIRKCUSKBLC-UHFFFAOYSA-N

物化性质

• 熔点：
  86-87 °C
• 沸点：
  307.3±27.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chloro-phenyl)-3-oxo-hexanenitrile 在 硫酸 、 sodium ethanolate 作用下， 生成 5-phenylnonan-4-one
  参考文献：
  名称：

  Ishiwata; Suzuki, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 1272

  摘要：

  DOI：
• 作为产物：
  描述：

  丁酸乙酯 、 对氯苯乙腈 在 sodium ethanolate 作用下， 生成 2-(4-chloro-phenyl)-3-oxo-hexanenitrile
  参考文献：
  名称：

  2,4-Diaminopyrimidines as Antimalarials. III. 5-Aryl Derivatives

  摘要：

  DOI：

  10.1021/ja01152a060

文献信息

• Oxidative aromatic C–N bond formation: convenient synthesis of N-amino-3-nitrile-indoles via FeBr3-mediated intramolecular cyclization
  作者：Zisheng Zheng、Lina Tang、Yanfeng Fan、Xiuxiang Qi、Yunfei Du、Daisy Zhang-Negrerie

  DOI：10.1039/c1ob05069a

  日期：——

  functionalized N-amino-3-nitrile-indole derivatives are obtained via an intramolecular hetero-cyclization of 2-aryl-3-substituted hydrazono-alkylnitriles using FeBr3 as a single electron oxidant. This approach allows the N-moiety on the side-chain to be annulated to the benzene ring during the final synthetic step via direct oxidative aromatic C–N bond formation.

  通过使用FeBr 3作为单电子氧化剂，通过2-芳基-3-取代的肼基-烷基腈的分子内杂环化，可获得各种官能化的N-氨基-3-腈-吲哚衍生物。这种方法允许在最后的合成步骤中，通过直接氧化芳族C–N键的形成，将侧链上的N部分环合到苯环上。
• Synthesis of 1,2-Diketones from β-Keto Nitriles via a Protection-Oxidative-Decyanation-Deprotection Protocol
  作者：Yunfei Du、Kang Zhao、Yu Liu、Xiliu Yun、Daisy Zhang-Negrerie、Jianhui Huang

  DOI：10.1055/s-0030-1260156

  日期：2011.9

  were prepared from β-keto nitriles via a three-step protocol including the protection of the ketones with methoxyamine, oxidative decyanation, and microwave-assisted deprotection in the final step. This approach provides a novel and efficient access to a wide scope of symmetric and unsymmetric 1,2-diketones using molecular oxygen as the oxidant in the decyanation process. β-keto nitriles - oxygen - oxidative

  通过三步方案从β-酮腈制备了各种1,2-二酮，包括在最后一步用甲氧基胺保护酮，氧化脱氰和微波辅助脱保护。这种方法在脱氰过程中使用分子氧作为氧化剂，提供了一种新颖而有效的途径，可以广泛地使用对称和不对称的1,2-二酮。 β-酮腈-氧气-氧化脱氰-微波-1,2-二酮
• Synthesis of N-Substituted Indole Derivatives via PIFA-Mediated Intramolecular Cyclization
  作者：Yunfei Du、Renhe Liu、Gregory Linn、Kang Zhao

  DOI：10.1021/ol062288o

  日期：2006.12.1

  A variety of N- arylated and N- alkylated indole derivatives were synthesized by way of a phenyliodine bis( trifluoroacetate) ( PIFA)- mediated intramolecular cyclization. This novel method allows for the construction of an indole skeleton by joining the N- atom on the side chain to the benzene ring at the last synthetic step. Other novel pyrrole- fused aromatic compounds can also be achieved by this method.
• Pyrimethamine Derivatives: Insight into Binding Mechanism and Improved Enhancement of Mutant β-<i>N</i>-acetylhexosaminidase Activity
  作者：Michael B. Tropak、Jianmin Zhang、Sayuri Yonekawa、Brigitte A. Rigat、Virender S. Aulakh、Matthew R. Smith、Hee-Jong Hwang、Marco A. Ciufolini、Don J. Mahuran

  DOI：10.1021/jm5017895

  日期：2015.6.11

  In order to identify structural features of pyrimethamine (5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine) that contribute to its inhibitory activity (IC50 value) and chaperoning efficacy toward beta-N-acetylhexosaminidase, derivatives of the compound were synthesized that differ at the positions bearing the amino, ethyl, and chloro groups. Whereas the amino groups proved to be critical to its inhibitory activity, a variety of substitutions at the chloro position only increased its IC50 by 2-3-fold. Replacing the ethyl group at the 6-position with butyl or methyl groups increased IC50 more than 10-fold. Surprisingly, despite its higher IC50, a derivative lacking the chlorine atom in the para-position was found to enhance enzyme activity in live patient cells a further 25% at concentrations >100 mu M, while showing less toxicity. These findings demonstrate the importance of the phenyl group in modulating the chaperoning efficacy and toxicity profile of the derivatives.