2-(4-溴苯胺基)-2-苯基乙腈 | 7510-78-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-(4-溴苯胺基)-2-苯基乙腈
• 英文名称: 2-((4-bromophenyl)amino)-2-phenylacetonitrile
• 英文别名: 2-((p-bromophenyl)amino)-2-phenylacetonitrile；2-(4-bromophenylamino)-2-phenylacetonitrile；2-[N-(4-bromoanilino)]-2-phenylacetonitrile；2-(N-4-bromoanilino)-2-phenylacetonitrile；α-cyano-N-benzyl-4-bromoaniline；(4-bromo-anilino)-phenyl-acetonitrile；2-(4-Bromoanilino)-2-phenylacetonitrile
• CAS: 7510-78-3
• 化学式: C₁₄H₁₁BrN₂
• 分子量: 287.159
• InChiKey: SVPCPLZZQODKMJ-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93 °C(Solv: ethanol (64-17-5))
• 沸点：
  412.8±40.0 °C(Predicted)
• 密度：
  1.461±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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-(4-溴苯胺基)-2-苯基乙腈 生成 (4-bromo-phenylimino)-phenyl-acetonitrile
  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
• 作为产物：
  描述：

  1-(methylsulfonyl)-2-(4-bromophenyl)diazene 在 sodium tetrahydroborate 、 乙醇 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-(4-溴苯胺基)-2-苯基乙腈
  参考文献：
  名称：

  C_sp3–H Imination Using Arylazo Sulfone as a N Source: An Approach to Access Imines

  摘要：

  DOI：

  10.1021/acs.orglett.3c02283

文献信息

• Zr(HSO4)4 catalyzed one-pot strecker synthesis of α-amino nitriles from aldehydes and ketones under solvent-free conditions
  作者：A. R. Hajipour、Y. Ghayeb、N. Sheikhan

  DOI：10.1007/bf03246031

  日期：2010.6

  A mild and efficient method has been developed for the preparation of α-amino nitriles from the condensation of aldehydes and ketones with aniline and TMSCN in the presence of a catalytic amount of Zr(HSO4)4 under solvent-free conditions at room temperature.

  已经开发了一种温和有效的方法，在室温下在无溶剂条件下，在催化量的Zr（HSO 4）4存在下，由醛和酮与苯胺和TMSCN缩合制备α-氨基腈。
• K2PdCl4 catalyzed efficient multicomponent synthesis of α-aminonitriles in aqueous media
  作者：Bikash Karmakar、Julie Banerji

  DOI：10.1016/j.tetlet.2010.03.059

  日期：2010.5

  An efficient, mild and environmentally friendly method has been developed for the Strecker reaction to synthesize α-aminonitriles in the presence of K2PdCl4 as a catalyst. The three-component one-pot condensation of an aldehyde, amine and trimethylsilyl cyanide proceeded smoothly in water to afford the corresponding product in high yield with short reaction times.

  已经开发出一种有效，温和且环保的方法，用于在存在K 2 PdCl 4作为催化剂的情况下进行Strecker反应以合成α-氨基腈。醛，胺和三甲基甲硅烷基氰化物的三组分一锅缩合在水中平稳进行，以高收率和短反应时间提供相应的产物。
• Boric Acid Catalysed Synthesis of α-Aminonitriles by a Three-Component Reaction at Room Temperature
  作者：Zahed Karimi-Jaberi、Abdolaziz Bahrani

  DOI：10.3184/174751912x13352842814921

  日期：2012.6

  A simple, efficient, and cost-effective method has been developed for the one-pot, three-component condensation reaction of trimethylsilyl cyanide, aldehydes and aromatic amines using boric acid as a heterogeneous solid acid catalyst, under solvent-free conditions. α-Aminonitriles were synthesised relatively quickly in good yields at room temperature.

  开发了一种简单、高效且经济的方法，用于在无溶剂条件下使用硼酸作为非均相固体酸催化剂进行三甲基氰化硅烷、醛和芳香胺的一锅三组分缩合反应。α-氨基腈在室温下以良好的收率相对较快地合成。
• A unique combination of KI/ZnFe₂O₄as a catalyst for oxidative Strecker reaction
  作者：Leila Ghandi、Maryam Kazemi Miraki、Meghdad Karimi、Iman Radfar、Akbar Heydari

  DOI：10.1002/aoc.4616

  日期：2019.1

  α‐Aminonitriles as key intermediates for the preparation of α‐amino acid derivatives, amides, diamines, peptides, proteins and heterocycles were synthesized through methylarene oxidation in the Strecker reaction using a unique combination of KI/ZnFe2O4 as the best catalyst and aqueous tert‐butyl hydroperoxide as oxidant. A wide range of amines and methylarenes were converted to the corresponding products

  α-氨基腈是制备α-氨基酸衍生物，酰胺，二胺，肽，蛋白质和杂环的关键中间体，是在Strecker反应中通过甲基芳烃氧化合成的，采用独特的KI / ZnFe 2 O 4作为最佳催化剂，叔丁基过氧化氢水溶液作氧化剂。多种胺和甲基芳烃被转化为相应的产物。操作简便，反应时间短和催化剂的可回收性是该方案的优势。
• Cyano-borrowing: titanium-catalyzed direct amination of cyanohydrins with amines and enantioselective examples
  作者：Tang-Lin Liu、Zhao-Feng Li、Jing Tao、Qing-Hua Li、Wan-Fang Li、Qian Li、Li-Qing Ren、Yun-Gui Peng

  DOI：10.1039/c9cc08576a

  日期：——

  The direct amination of cyanohydrins with amines via a catalytic cyano-borrowing reaction was developed. The transformation features broad substrate scope, excellent functional group compatibility, and very mild and simple operations. Moreover, a titanium catalyst supported by quinine and (S)-BINOL ligands enabled an asymmetric cyano-borrowing reaction with moderate to high enantioselectivity.

  开发了通过催化氰基借位反应将氰醇与胺直接胺化的方法。该转化具有广泛的底物范围，出色的官能团相容性以及非常温和和简单的操作。此外，由奎宁和（S）-BINOL配体负载的钛催化剂能够实现不对称的氰基-借位反应，具有中等至高的对映选择性。