(对氯苯基)丁二腈 | 108005-47-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (对氯苯基)丁二腈
• 英文名称: 2-(4-chlorophenyl)succinonitrile
• 英文别名: (p-chlorophenyl)succinonitrile；2-(4-chlorophenyl)butanedinitrile
• CAS: 108005-47-6
• 化学式: C₁₀H₇ClN₂
• 分子量: 190.632
• InChiKey: HDKXIEAROJEEDG-UHFFFAOYSA-N

物化性质

• 熔点：
  88-89 °C
• 沸点：
  381.0±27.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (对氯苯基)丁二腈 在 硫酸 、 溶剂黄146 作用下， 反应 1.0h， 以55%的产率得到3-(4-氯苯基)吡咯烷-2,5-二酮
  参考文献：
  名称：

  Metabolism of 3-(p-chlorophenyl)pyrrolidine. Structural effects in conversion of a prototype .gamma.-aminobutyric acid prodrug to lactam and .gamma.-aminobutyric acid type metabolites

  摘要：

  By use of rat liver or brain homogenate supernatants containing microsomes and/or mitochondria, it was found that the prototype GABAergic prodrug [3-(p-chlorophenyl)pyrrolidine (1)] underwent a series of alpha-oxidation transformations to a pair of amino acid metabolites and a pair of lactam metabolites [4-amino-3-(p-chlorophenyl)butanoic acid, baclofen (5); 4-amino-2-(p-chlorophenyl)butanoic acid (10); 4-(chlorophenyl)pyrrolidin-2-one and 3-(p-chlorophenyl)pyrrolidine-2-one (11)]. With the liver homogenates, the formation of the lactam metabolites was approximately 2 orders of magnitude greater than that of the amino acid metabolites, while with the brain homogenates, the amino acid and lactam pathways were of similar magnitude. For either tissue, for both the lactam and the amino acid series, attack at the less sterically hindered 5-position of the pyrrolidine ring was greater than the attack at the 2-position (5 greater than 10 and 6 greater than 11) with the exception of the liver homogenate mitochondrial fraction (6 less than 11). The parenteral administration of the prodrug 1 was found to give detectable brain levels of 5 as well as activity in an isoniazid-induced (GABA-inhibited) convulsion model.

  DOI：

  10.1021/jm00126a033
• 作为产物：
  描述：

  4-氯苯甲醛 在 四丁基氟化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 6.0h， 生成 (对氯苯基)丁二腈
  参考文献：
  名称：

  由四丁基氟化铵介导的硝基烯烃和氰化甲硅烷基直接合成1,2-二氰基烷烃

  摘要：

  描述了在氟化四丁基铵存在下，使硝基烯烃与三甲基甲硅烷基氰化物反应，直接合成1,2-二氰基烷烃的方法。反应在温和条件下通过串联双迈克尔加成反应进行。使用由三甲基甲硅烷基氰化物和四丁基氟化铵生成的高价硅酸盐对于实现这种转化至关重要。机理研究表明，反应介质中包含的少量水起着关键作用。该协议适用于各种类型的底物，包括富电子和缺电子的芳族硝基烯烃，以及脂肪族硝基烯烃。此外，发现乙烯基砜是很好的替代品，特别是对于缺电子的硝基烯烃。

  DOI：

  10.1002/chem.201404780

文献信息

• Ring Opening of Donor–Acceptor Cyclopropanes with Cyanide Ion and Its Surrogates
  作者：Maksim A. Boichenko、Ivan A. Andreev、Alexey O. Chagarovskiy、Irina I. Levina、Sergey S. Zhokhov、Igor V. Trushkov、Olga A. Ivanova

  DOI：10.1021/acs.joc.9b03098

  日期：2020.1.17

  A straightforward method for ring opening of donor-acceptor cyclopropanes with trimethylsilyl cyanide as a surrogate of cyanide ion in the presence of B(C6F5)3 or trifluoromethanesulfonic acid as a catalyst has been developed. The methodology provides a short route to γ-cyanoesters that can be useful synthetic intermediates for the synthesis of diverse bioactive molecules such as glutaric and δ-aminovaleric

  已开发出一种简单的方法，用于在B（C6F5）3或三氟甲磺酸作为催化剂的情况下，使用三甲基甲硅烷基氰化物作为氰化物离子的替代物来开环供体-受体环丙烷。该方法为γ-氰基酯提供了一条捷径，γ-氰基酯可以用作合成多种生物活性分子（如戊二酸和δ-氨基戊酸衍生物，3-芳基哌啶或其他取代的苯乙胺）的有用合成中间体。相反，在典型的SN2条件下通过环丙烷与氰化钠直接反应合成这些γ-氰基酯的尝试导致了2-芳基琥珀腈的形成。
• Reductive Arylation of Maleic and Fumaric Acid Derivatives by Arenediazonium and Titanium(III) Salts
  作者：Attilio Citterio、Alberto Cominelli、Francesco Bonavoglia

  DOI：10.1055/s-1986-31593

  日期：——

  The titanium(III)-induced decomposition of substituted benzenediazonium salts in the presence of maleic and furamic acids, alkyl esters, amides, and nitriles gives the corresponding arylsuccinic acid derivatives.

  在马来酸和富拉酸、烷基酯、酰胺和腈的存在下，钛（III）诱导取代的苯偶氮盐分解，产生相应的芳基丁二酸衍生物。
• Light‐Induced Divergent Cyanation of Alkynes Enabled by Phosphorus Radicals
  作者：Yanyan Zhang、Yunhong Han、Shengqing Zhu、Feng‐Ling Qing、Xiao‐Song Xue、Lingling Chu

  DOI：10.1002/anie.202210838

  日期：2022.12.12

  A photochemically induced selective and divergent cyanation reaction of alkynes, enabled by phosphorus radicals, is described. With the use of simple triarylphosphine as a co-catalyst, three cyanation reactions, including di-hydrocyanation, anti-Markovnikov hydrocyanation, and domino hydrocyanation/reduction, can be divergently achieved, furnishing a wide array of alkyl dinitriles, alkenyl nitriles

  描述了由磷自由基​​启用的光化学诱导的炔烃选择性和发散氰化反应。使用简单的三芳基膦作为助催化剂，可以发散地实现包括二氢氰化、反马尔可夫尼科夫氢氰化和多米诺氢氰化/还原在内的三种氰化反应，提供范围广泛的烷基二腈、烯基腈和烷基温和条件下的腈类。
• CITTERIO A.; COMINELLI A.; BONAVOGLIA F., SYNTHESIS,(1986) N 4, 308-309
  作者：CITTERIO A.、 COMINELLI A.、 BONAVOGLIA F.

  DOI：——

  日期：——
• Metabolism of 3-(p-chlorophenyl)pyrrolidine. Structural effects in conversion of a prototype .gamma.-aminobutyric acid prodrug to lactam and .gamma.-aminobutyric acid type metabolites
  作者：G. Michael Wall、John K. Baker

  DOI：10.1021/jm00126a033

  日期：1989.6

  By use of rat liver or brain homogenate supernatants containing microsomes and/or mitochondria, it was found that the prototype GABAergic prodrug [3-(p-chlorophenyl)pyrrolidine (1)] underwent a series of alpha-oxidation transformations to a pair of amino acid metabolites and a pair of lactam metabolites [4-amino-3-(p-chlorophenyl)butanoic acid, baclofen (5); 4-amino-2-(p-chlorophenyl)butanoic acid (10); 4-(chlorophenyl)pyrrolidin-2-one and 3-(p-chlorophenyl)pyrrolidine-2-one (11)]. With the liver homogenates, the formation of the lactam metabolites was approximately 2 orders of magnitude greater than that of the amino acid metabolites, while with the brain homogenates, the amino acid and lactam pathways were of similar magnitude. For either tissue, for both the lactam and the amino acid series, attack at the less sterically hindered 5-position of the pyrrolidine ring was greater than the attack at the 2-position (5 greater than 10 and 6 greater than 11) with the exception of the liver homogenate mitochondrial fraction (6 less than 11). The parenteral administration of the prodrug 1 was found to give detectable brain levels of 5 as well as activity in an isoniazid-induced (GABA-inhibited) convulsion model.