3-(4-chlorobenzoyl)benzonitrile | 35256-77-0

• 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: 3-(4-chlorobenzoyl)benzonitrile
• 英文别名: 4-chloro-3'-cyanobenzophenone；3-p-chlorobenzoyl-benzonitrile；3-Cyano-4'-chlorbenzophenon；Benzonitrile, 3-(4-chlorobenzoyl)-
• CAS: 35256-77-0
• 化学式: C₁₄H₈ClNO
• 分子量: 241.677
• InChiKey: IFSAYMSDTKCGKT-UHFFFAOYSA-N

物化性质

• 熔点：
  139-140 °C
• 沸点：
  401.7±30.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3-(4-chlorobenzoyl)benzonitrile 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis and structure–activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents

  摘要：

  KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the dike-topiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we further modified the benzophenone moiety of 4. Accordingly, we obtained a 4-fluorobenzophenone derivative 16j that inhibited tumor cell growth in vitro with a subnanomolar IC50 value against HT-29 cells (IC50 = 0.5 nM). Next, the effect of 16j on mitotic spindles was evaluated in HeLa cells. Treatment with 3 nM of 16j partially disrupted the interphase microtubule network. By contrast, treatment with the same concentration of CA-4 barely affected the microtubule network, indicating that 16j exhibited more potent anti-mitotic effects than did CA-4. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.059
• 作为产物：
  描述：

  对氯苯甲酸 在 正丁基锂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 3-(4-chlorobenzoyl)benzonitrile
  参考文献：
  名称：

  Synthesis and structure–activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents

  摘要：

  KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the dike-topiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we further modified the benzophenone moiety of 4. Accordingly, we obtained a 4-fluorobenzophenone derivative 16j that inhibited tumor cell growth in vitro with a subnanomolar IC50 value against HT-29 cells (IC50 = 0.5 nM). Next, the effect of 16j on mitotic spindles was evaluated in HeLa cells. Treatment with 3 nM of 16j partially disrupted the interphase microtubule network. By contrast, treatment with the same concentration of CA-4 barely affected the microtubule network, indicating that 16j exhibited more potent anti-mitotic effects than did CA-4. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.059

文献信息

• Ligand‐free Palladium‐Catalyzed Carbonylative Suzuki Coupling of Aryl Iodides in Aqueous CH ₃ CN with Sub‐stoichiometric Amount of Mo(CO) ₆ as CO Source
  作者：Nan Sun、Qingxia Sun、Wei Zhao、Liqun Jin、Baoxiang Hu、Zhenlu Shen、Xinquan Hu

  DOI：10.1002/adsc.201900011

  日期：2019.4.23

  established based on the palladium‐catalyzed carbonylative Suzuki coupling approach with sub‐stoichiometric Mo(CO)6 as CO source. Using 0.5 mol% of Pd(TFA)2 as catalyst, 0.5 equivalent of Mo(CO)6 as solid carbonyl reagent and 3 equivalent of K3PO4 as base, a wide range of functionalized (hetero)aryl iodides and (hetero)aryl boronic acids could smoothly proceed the carbonylative cross‐coupling reaction in aqueous

  基于亚化学计量的Mo（CO）6作为CO源的钯催化羰基化Suzuki偶联方法，已经建立了一种合成二芳基和杂二芳基酮的新方法。使用0.5摩尔％的Pd（TFA）2作为催化剂，0.5当量的Mo（CO）6作为固体羰基试剂和3当量的K 3 PO 4作为碱，各种官能化的（杂）芳基碘和（杂）芳基硼酸可以在50°C的CH 3 CN水溶液中平稳地进行羰基交叉偶联反应，从而提供相应的酮，收率非常好。新开发的方法易于在温和条件下高效地操作。
• A phosphine-free carbonylative cross-coupling reaction of aryl iodides with arylboronic acids catalyzed by immobilization of palladium in MCM-41
  作者：Mingzhong Cai、Jian Peng、Wenyan Hao、Guodong Ding

  DOI：10.1039/c0gc00138d

  日期：——

  heterogeneous carbonylative cross-coupling of aryl iodides with arylboronic acids under an atmospheric pressure of carbon monoxide was achieved in anisole at 80 °C in the presence of a 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized palladium(II) complex [MCM-41–2N–Pd(II)], yielding a variety of unsymmetrical biaryl ketones in good to high yield. This heterogeneous palladium catalyst exhibited

  这 膦大气压下芳基碘化物与芳基硼酸的无价异质羰基交叉偶联 一氧化碳 在 苯甲醚 在80°C下 3-（2-氨基乙基氨基）丙基官能化 固定MCM-41 钯（II） 复合[MCM-41–2N–钯（II）]，生成各种不对称的联芳基 酮类高产到高产。这种异质钯 催化剂 表现出更高的活性和选择性 氯化钯2（PPh 3）2，可以通过简单的方法进行回收和再利用 过滤反应溶液，并用于至少10次连续试验而活性没有降低。我们的系统不仅避免使用膦 配体，也解决了基本问题 钯 催化剂 恢复和重用。
• Carbonylative Suzuki-Miyaura Coupling of Arylboronic Acids with Aryl Iodides Catalyzed by the MCM-41-Supported Bidentate Phosphane Palladium(II) Complex
  作者：Mingzhong Cai、Guomin Zheng、Lingfang Zha、Jian Peng

  DOI：10.1002/ejoc.200801253

  日期：2009.4

  pressure of carbon monoxide has been achieved in anisole at 80 °C in the presence of a catalytic amount of an MCM-41-supported bidentate phosphane palladium(II) complex (MCM-41-2P-PdII), yielding unsymmetrical biaryl ketones in good-to-high yields. This polymeric palladium catalyst exhibited higher activity and selectivity than [PdCl2(PPh3)2] and can be reused at least 10 times without any decrease in activity

  在催化量的 MCM-41 负载的双齿磷烷钯存在下，在 80°C 下，在一氧化碳的大气压下，芳基硼酸与芳基碘化物的第一个非均相羰基化 Suzuki-Miyaura 交叉偶联反应已在苯甲醚中实现(II) 复合物 (MCM-41-2P-PdII)，以从良到高的产率产生不对称的联芳基酮。这种聚合钯催化剂表现出比 [PdCl2(PPh3)2] 更高的活性和选择性，并且可以重复使用至少 10 次而不会降低活性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Enzyme-Catalyzed Enantioselective Diaryl Ketone Reductions
  作者：Matthew D. Truppo、David Pollard、Paul Devine

  DOI：10.1021/ol0627909

  日期：2007.1.1

  The synthesis of diarylmethanols via the reduction of a range of substituted benzophenone and benzoylpyridine derivatives with ketoreductase enzymes (KREDs) has afforded chiral products with high yield (>90%) and ee (up to >99%). Ortho, meta, and para substitutions with a variety of electron-donating, electron-withdrawing, and halogen groups were examined. Substitution at the ortho position and/or

  通过用酮还原酶（KREDs）还原一系列取代的二苯甲酮和苯甲酰基吡啶衍生物来合成二芳基甲醇，已得到具有高收率（> 90％）和ee（最高> 99％）的手性产物。考察了具有各种供电子，吸电子和卤素基团的邻位，间位和对位取代。与常规化学催化剂还原的情况一样，对于良好的选择性，不需要在邻位上取代和/或高度电子不对称的分子。[反应：请参见文字]。
• Novel benzoylphenylacetic acid esters
  申请人：Roussel Uclaf

  公开号：US04192890A1

  公开（公告）日：1980-03-11

  Racemates [and optically active isomers of benzoylphenylacetic acid esters of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 7 carbon atoms, and the two benzene rings may be optionally substituted with at least one member of the group consisting of chlorine, fluorine, bromine, trifluoromethyl and alkyl and alkoxy and alkylthio of 1 to 7 carbon atoms], intermediates and process for their preparation and their use as analgesics and antiinflammatory agents.

  盐酸苯甲酰基苯乙酸酯的外消旋体和光学活性异构体的制备方法，其中R选择自氢和1至7个碳原子的烷基组成的群，两个苯环可以选择性地与至少一种氯、氟、溴、三氟甲基、1至7个碳原子的烷基、烷氧基和烷硫基中的一种成员取代，以及它们作为止痛剂和抗炎药物的用途。