2-[N-(1-naphthylamino)]-2-phenylacetonitrile | 88485-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[N-(1-naphthylamino)]-2-phenylacetonitrile
• 英文别名: [1]naphthylamino-phenyl-acetonitrile；α-(α-Naphthylamino)-phenylessigsaeure-nitril；(α-Cyan-benzyl)-α-naphthylamin；[1]Naphthylamino-phenyl-acetonitril；2-(Naphthalen-1-ylamino)-2-phenylacetonitrile
• CAS: 88485-94-3
• 化学式: C₁₈H₁₄N₂
• 分子量: 258.323
• InChiKey: NHSHPIFTBCJELL-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  453.6±33.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-(1-naphthylamino)]-2-phenylacetonitrile 在 potassium permanganate 、 丙酮 作用下， 生成 [1]naphthylimino-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：

  N-亚苄基-1-萘胺 、 alkaline earth salt of/the/ methylsulfuric acid 生成 2-[N-(1-naphthylamino)]-2-phenylacetonitrile
  参考文献：
  名称：

  DE157617

  摘要：

  公开号：

文献信息

• 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。
• Magnetic Fe3O4–BF3: highly efficient Lewis acid catalyst for the synthesis of α-aminonitriles
  作者：Mohsen Shekouhy、Ali Moaddeli、Ali Khalafi-Nezhad

  DOI：10.1007/s11164-015-2246-4

  日期：2016.4

  magnetically separable Lewis acid catalyst and successfully used for the one-pot synthesis of α -aminonitriles. A broad range of substrates including the aromatic and heteroaromatic aldehydes, cyclic ketones (cyclopentanone, cyclohexanone and cycloheptanone), aryl–alkyl ketones, diaryl ketones and tetralones, isatin derivatives and acenaphthenequinone were condensed with amines (aliphatic and aromatic) and trimethylsilyl

  制备了Fe 3 O 4磁性纳米颗粒负载的BF 3作为新型的可磁分离的路易斯酸催化剂，并成功用于一锅法合成 α- 氨基腈。广泛的底物包括芳族和杂芳族醛，环酮（环戊酮，环己酮和环庚酮），芳基-烷基酮，二芳基酮和四氢萘酮，靛红衍生物和苯醌与胺（脂族和芳族）和三甲基甲硅烷基氰化物缩合。所有反应均在短时间内完成，并以良好至极好的收率获得了产物。该催化剂可以循环使用几次，而不会降低效率。最后， α 含腺嘌呤的-氨基腈已成功合成。
• 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。
• FeCl₃-Catalyzed Decyanative [4 + 2] Annulation of α-Aminonitriles with Alkynes: Access to 2,4-Diaryl Quinolines in Batch and Continuous-Flow Processes
  作者：Swetha Sathyendran、Kesavan Muthu、Karthick Govindan、Nian-Qi Chen、Wei-Yu Lin、Gopal Chandru Senadi

  DOI：10.1021/acs.orglett.3c01306

  日期：2023.6.9

  FeCl3-catalyzed decyanation of α-aminonitriles followed by a [4 + 2] annulation with terminal alkynes has been developed to synthesize 2,4-diaryl quinolines. A broad range of aniline, aldehyde, and arylacetylene derivatives were well tolerated to access 2,4-diaryl quinolines in moderate to good yields. The control experiment studies suggested that the reaction proceeds through a nonradical pathway

  已开发出FeCl 3催化的 α-氨基腈脱氰反应，然后与末端炔烃进行 [4 + 2] 环化，以合成 2,4-二芳基喹啉。广泛的苯胺、醛和芳基乙炔衍生物具有良好的耐受性，能够以中等到良好的收率获得 2,4-二芳基喹啉。对照实验研究表明，反应通过非自由基途径进行，涉及从原位生成的亚铵物种的 Povarov 型 [4 + 2] 环化。该策略的合成应用 (i) 包括克级合成和 (ii) 在较短的反应时间（22 分钟）内对一些代表性化合物进行连续流动过程，以及 (iii) 作为概念证明与苯乙烯一起使用效果很好.
• Barnikow; Hagen; Hagen, Pharmazie, 1983, vol. 38, # 7, p. 449 - 452
  作者：Barnikow、Hagen、Hagen、Goeres、Richter、Fichtner

  DOI：——

  日期：——