2-[N-(3-methylanilino)]-2-phenylacetonitrile | 15190-17-7

• 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: 2-[N-(3-methylanilino)]-2-phenylacetonitrile
• 英文别名: α-cyano-N-benzyl-3-methylaniline；2-(m-tolylamino)-2-phenylacetonitrile；2-phenyl-2-(m-tolylamino)acetonitrile；phenyl-m-toluidino-acetonitrile；α-m-Toluidino-phenylessigsaeure-nitril；Phenyl-m-toluidino-acetonitril；2-(3-Methylanilino)-2-phenylacetonitrile
• CAS: 15190-17-7
• 化学式: C₁₅H₁₄N₂
• 分子量: 222.29
• InChiKey: ZOLWTYHOBNDSPX-UHFFFAOYSA-N

物化性质

• 熔点：
  94-96 °C
• 沸点：
  384.5±30.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[N-(3-methylanilino)]-2-phenylacetonitrile 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以97%的产率得到Phenyl-m-tolylamino-acetic acid; hydrochloride
  参考文献：
  名称：

  Naim, S. Shawkat; Khan, Naseem H.; Siddiqui, Amin A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 7, p. 622 - 624

  摘要：

  DOI：
• 作为产物：
  描述：

  扁桃腈 、 3-甲基苯胺 生成 2-[N-(3-methylanilino)]-2-phenylacetonitrile
  参考文献：
  名称：

  LAPAROSCOPIC NEPHROURETERECTOMY FOR UPPER TRACT TRANSITIONAL CELL CANCER: THE WASHINGTON UNIVERSITY EXPERIENCE

  摘要：

  Purpose: Laparoscopic nephroureterectomy has only recently been done to treat patients with upper tract transitional cell carcinoma. We retrospectively evaluated our experience with and long-term followup of laparoscopic nephroureterectomy, compared our results to those of contemporary series of open nephroureterectomy and reviewed the literature.Materials and Methods: We reviewed the charts of and followed up by telephone 25 patients who underwent laparoscopic nephroureterectomy between May 1991 and June 1998, and 17 who underwent open nephroureterectomy between March 1990 and January 1997. Demographic, perioperative and followup data were compared. We performed a MEDLINE search and reviewed the literature on laparoscopic nephroureterectomy for upper tract transitional cell carcinoma.Results: Laparoscopic nephroureterectomy required twice the operating time of open nephroureterectomy (7.7 versus 3.9 hours). However, patients who underwent the laparoscopic procedure had a 74% decrease in analgesia requirements (37 versus 144 mg. morphine sulfate equivalent), a 63% shorter hospital stay (3.6 versus 9.6 days) and a 72% more rapid convalescence (2.8 versus 10 weeks). Subsequent bladder transitional cell carcinoma and overall cancer specific survival were similar at a mean followup of 2 years. There was no sign of trocar site or peritoneal seeding after laparoscopic nephroureterectomy.Conclusions: Although laparoscopic nephroureterectomy is a longer operation, it has the same efficacy and is better tolerated by patients than open nephroureterectomy for upper tract transitional cell carcinoma. As operating time decreases due to surgeon experience and the recent development of hand assisted laparoscopy, laparoscopic nephroureterectomy may soon become the procedure of choice for the ablative management of upper tract transitional cell carcinoma.

  DOI：

  10.1016/s0022-5347(05)67701-4

文献信息

• Efficient Three-Component Strecker Reaction of Acetals and Aromatic Amines Catalysed by Hafnium Tetrachloride at Room Temperature
  作者：Xue-Lin Zhang、Qin-Pei Wu、Qing-Shan Zhang

  DOI：10.3184/174751913x13814077309487

  日期：2013.11

  A straightforward, mild, efficient, one-pot method has been found for the synthesis of α-aminonitriles via three-component Strecker reaction using acetals or cyclic acetals, curious aromatic amines and trimethylsilyl cyanide (TMSCN) catalysed by hafnium tetrachloride at room temperature. It is with good to excellent yields under mild conditions. This developed approach has been successfully applied

  已经找到了一种简单、温和、高效的一锅法，通过三组分 Strecker 反应，使用缩醛或环状缩醛、奇怪的芳香胺和三甲基氰化硅烷 (TMSCN) 在室温下由四氯化铪催化合成 α-氨基腈。它在温和的条件下具有良好的收率。这种开发的方法已成功应用于合成具有多种官能团的各种α-氨基腈。
• One-pot three-component synthesis of α-aminonitriles using potassium hexacyanoferrate(II) as an eco-friendly cyanide source
  作者：Zheng Li、Yuanhong Ma、Jun Xu、Jinghong Shi、Hongfang Cai

  DOI：10.1016/j.tetlet.2010.05.088

  日期：2010.7

  been developed for the synthesis of α-aminonitriles via one-pot three-component condensation of carbonyl compounds, amines, and potassium hexacyanoferrate(II) in the presence of benzoyl chloride as a promoter. This protocol has the features of use of eco-friendly cyanide source, high yield, and simple work-up procedure.

  在苯甲酰氯作为促进剂存在下，通过羰基化合物，胺和六氰合铁酸钾（II）的一锅式三组分缩合反应，已开发出一种有效且环保的方法来合成α-氨基腈。该协议具有使用环保型氰化物源，高收率和后处理程序简单的特点。
• Role of (3-aminopropyl)tri alkoxysilanes in grafting of chlorosulphonic acid immobilized magnetic nanoparticles and their application as heterogeneous catalysts for the green synthesis of α-aminonitriles
  作者：Harminder Singh、Jaspreet Kaur Rajput、Priya Arora、Jigyasa Jigyasa

  DOI：10.1039/c6ra20095h

  日期：——

  organic–inorganic hybrid magnetic heterogeneous catalysts. The silanization was carried out on the surface of SiO2 coated Fe3O4 nanoparticles using two different trialkoxy silanes, i.e., 3-aminopropyltriethoxysilane (APTES) and 3-aminopropyltrimethoxysilane (APMES). The effect of the alkoxy silane structure anchored to the surface of silica functionalized Fe3O4 nanoparticles on their surface area and pore volume

  通过接枝硅烷偶联剂对SiO 2包覆的Fe 3 O 4纳米粒子进行表面改性是提高无机磁芯与要固定的有机官能团之间的界面相互作用的非常重要的方法。然而，很少使用有机-无机杂化磁性非均相催化剂研究利用不同的硅烷烷氧基的硅烷接枝分子结构的影响。使用两种不同的三烷氧基硅烷，即在SiO 2包覆的Fe 3 O 4纳米颗粒的表面上进行硅烷化，3-氨基丙基三乙氧基硅烷（APTES）和3-氨基丙基三甲氧基硅烷（APMES）。通过BET分析仪分析了锚固在二氧化硅官能化的Fe 3 O 4纳米颗粒表面上的烷氧基硅烷结构的表面积和孔体积的影响。与APTMS相比，使用APTES进行的硅烷官能化可产生更高的表面积和孔体积。此外，将氯磺酸固定在APTES和APTMS官能化的SiO 2 @Fe 3 O 4上以水为溶剂，一锅合成α-氨基腈，成功地实现了纳米颗粒（AE和AM）的分离，并作为可磁分离的非均相催化剂发挥了作用。使用A
• Barnikow; Hagen; Hagen, Pharmazie, 1983, vol. 38, # 7, p. 449 - 452
  作者：Barnikow、Hagen、Hagen、Goeres、Richter、Fichtner

  DOI：——

  日期：——
• Gawad, Ibrahim I. Abd El; Harhash, Abd El-Hammid; El-Zahab, Mohamad M. M. Abou, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1980, vol. 35, # 6, p. 712 - 714
  作者：Gawad, Ibrahim I. Abd El、Harhash, Abd El-Hammid、El-Zahab, Mohamad M. M. Abou

  DOI：——

  日期：——