3-(2-chloroethyl)benzonitrile | 484065-64-7

• 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-(2-chloroethyl)benzonitrile
• 英文别名: 3-cyanophenethyl chloride
• CAS: 484065-64-7
• 化学式: C₉H₈ClN
• 分子量: 165.622
• InChiKey: WVEKGXWQEOKZJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  276.7±15.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2-chloroethyl)benzonitrile 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 、 sodium sulfite 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 苯 为溶剂， 反应 92.0h， 生成 2-(3-cyanophenyl)-N-{4-[(4-piperidyl)oxy]phenyl}ethanesulfonamide
  参考文献：
  名称：

  Design, synthesis and biological activity of YM-60828 derivatives: potent and orally-Bioavailable factor Xa inhibitors based on naphthoanilide and naphthalensulfonanilide templates

  摘要：

  Factor Xa (FXa) is a serine protease which plays a pivotal role in the coagulation cascade. The inhibition of FXa has received great interest as a potential target for the development of new antithrombotic drug. Herein we describe a series of novel 7-arnidino-2-naphthoanilide and 7-amidino-2-naphthalensulfonanilide derivatives which are potent FXa inhibitors. These scaffolds are rigid and are allowed to adopt an L-shape conformation which was estimated as the active conformation based on a docking study of YM-60828 with FXa. Optimization of the side chain at the central aniline nitrogen of 7-amidino-2-naphthoanilide has led to several potent and orally active FXa inhibitors. 5h (YM-169964), the best compound of these series, showed potent FXa inhibitory activity (IC50 = 3.9 nM) and effectively prolonged prothrombin time by 9.6-fold ex vivo Lit an oral dose of 3 mg/kg in squirrel monkeys. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00106-2
• 作为产物：
  描述：

  3-碘苯乙酸 在 四氯化碳 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 C₁₈H₁₄CuIN₄ 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 30.0h， 生成 3-(2-chloroethyl)benzonitrile
  参考文献：
  名称：

  室温下光诱导的铜（I）催化芳香卤化物的氰化

  摘要：

  已经开发出在室温下第一光诱导的铜（I）催化的芳族卤化物的氰化。的SP 2氰化反应呈现突出的耐受性官能团，包括伯胺和羧酸，和化学选择性至S Ñ 2反应性烷基氯化物。机理研究表明，该反应是通过芳基卤化物与激发的氰化铜（I）催化中间体之间的单电子转移（SET）发生的。

  DOI：

  10.1002/adsc.201700213

文献信息

• REMEDIES FOR NEUROPATHIC PAIN
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：EP1182193A1

  公开（公告）日：2002-02-27

  The present invention relates to a compound represented by Formula (I) below: (wherein A represents, for example, phenyl group substituted by R1 and R2, or an unsubstituted furyl group or an unsubstitued thienyl group; R1 represents, for example, hydrogen atom, fluorine atom, chlorine atom, trifluoromethyl group, nitro group, cyano group or methyl group while R2 represents, for example, hydrogen atom; R3 represents, for example, hydrogen atom or methyl group; R4 represents, for example, hydrogen atom or methyl group; R5 represents ethoxy group or isopropoxy group; X represents group: -CH(OH)- or methylene group; and Z represents, for example, a single bond or methylene group unsubstituted or substituted by hydroxyl group), and its salts, and medicinal compositions containing, as their active ingredient, the above compound or its salts. The compound of this invention, which is orally applicable, is highly effective for treating neuroapthic pain while presenting with fewer side-effects than do the conventional analgesics.

  本发明涉及一种化合物，其由以下通式(I)表示：(其中A代表例如被R1和R2取代的苯基，或未被取代的呋喃基或未被取代的噻吩基；R1代表例如氢原子、氟原子、氯原子、三氟甲基、硝基、氰基或甲基，而R2代表例如氢原子；R3代表例如氢原子或甲基；R4代表例如氢原子或甲基；R5代表乙氧基或异丙氧基；X代表基团：-CH(OH)-或亚甲基；Z代表例如单键或未被取代或被羟基取代的亚甲基)，及其盐，以及含有上述化合物或其盐作为活性成分的药物组合物。本发明的化合物可经口给药，对治疗神经痛性疼痛具有高度有效性，且相比传统镇痛药副作用更少。
• Photoinduced Copper(I)-Catalyzed Cyanation of Aromatic Halides at Room Temperature
  作者：Kicheol Kim、Soon Hyeok Hong

  DOI：10.1002/adsc.201700213

  日期：2017.7.17

  copper(I)-catalyzed cyanation of aromatic halides at room temperature has been developed. The sp2 cyanation reaction exhibits outstanding tolerance to functional groups including primary amines and carboxylic acids, and chemoselectivity to SN2-reactive alkyl chlorides. Mechanistic investigations indicate that the reaction occurs via a single-electron transfer (SET) between the aryl halide and an excited copper(I)

  已经开发出在室温下第一光诱导的铜（I）催化的芳族卤化物的氰化。的SP 2氰化反应呈现突出的耐受性官能团，包括伯胺和羧酸，和化学选择性至S Ñ 2反应性烷基氯化物。机理研究表明，该反应是通过芳基卤化物与激发的氰化铜（I）催化中间体之间的单电子转移（SET）发生的。
• Design, synthesis and biological activity of YM-60828 derivatives: potent and orally-Bioavailable factor Xa inhibitors based on naphthoanilide and naphthalensulfonanilide templates
  作者：Fukushi Hirayama、Hiroyuki Koshio、Tsukasa Ishihara、Susumu Watanuki、Shunichiro Hachiya、Hiroyuki Kaizawa、Takahiro Kuramochi、Naoko Katayama、Hiroyuki Kurihara、Yuta Taniuchi、Kazuo Sato、Yumiko Sakai-Moritani、Seiji Kaku、Tomihisa Kawasaki、Yuzo Matsumoto、Shuichi Sakamoto、Shin-ichi Tsukamoto

  DOI：10.1016/s0968-0896(02)00106-2

  日期：2002.8

  Factor Xa (FXa) is a serine protease which plays a pivotal role in the coagulation cascade. The inhibition of FXa has received great interest as a potential target for the development of new antithrombotic drug. Herein we describe a series of novel 7-arnidino-2-naphthoanilide and 7-amidino-2-naphthalensulfonanilide derivatives which are potent FXa inhibitors. These scaffolds are rigid and are allowed to adopt an L-shape conformation which was estimated as the active conformation based on a docking study of YM-60828 with FXa. Optimization of the side chain at the central aniline nitrogen of 7-amidino-2-naphthoanilide has led to several potent and orally active FXa inhibitors. 5h (YM-169964), the best compound of these series, showed potent FXa inhibitory activity (IC50 = 3.9 nM) and effectively prolonged prothrombin time by 9.6-fold ex vivo Lit an oral dose of 3 mg/kg in squirrel monkeys. (C) 2002 Elsevier Science Ltd. All rights reserved.