trans 1-(2-naphthyl)-2-(3-pyridyl)ethylene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: trans 1-(2-naphthyl)-2-(3-pyridyl)ethylene
• 英文别名: 3-[(E)-2-naphthalen-2-ylethenyl]pyridine
• 化学式: C₁₇H₁₃N
• 分子量: 231.297
• InChiKey: LYKXVZAJSYRSOA-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans 1-(2-naphthyl)-2-(3-pyridyl)ethylene 以 正己烷 、 苯 为溶剂， 反应 3.0h， 生成 (Z)-3-(2-(naphthalen-2-yl)vinyl)pyridine 、 1-azabenzophenanthrene 、 naphtho[2,1-h]quinoline
  参考文献：
  名称：

  Masetti, Fausto; Bartocci, Giampiero; Mazzucato, Ugo, Gazzetta Chimica Italiana, 1982, vol. 112, # 7/8, p. 255 - 260

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(naphthalen-2-ylethynyl)pyridine 在 水 、 potassium ethyl xanthogenate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以88%的产率得到trans 1-(2-naphthyl)-2-(3-pyridyl)ethylene
  参考文献：
  名称：

  黄原酸酯介导的以水为氢供体的炔烃半加氢合成（E）-烯烃†

  摘要：

  炔烃的半氢化是在实验室制备和工业中获得烯烃的最广泛使用的方法之一。过渡金属催化剂已针对此转化进行了广泛研究，但对吡啶，-OH，-NH 2，-Bpin和卤化物等官能团的耐受性以及微量过渡金属催化剂的毒性仍极具挑战性。在这项研究中，我们报告了使用廉价的市售黄药作为介质，实现炔烃半加氢的通用且稳健的策略。机理研究支持非自由基过程，H 2 O充当氢供体。

  DOI：

  10.1039/c9cc00128j

文献信息

• Model Guided Development of a Simple Catalytic Method for the Synthesis of Unsymmetrical Stilbenes by Sequential Heck Reactions of Aryl Bromides with Ethylene
  作者：Helen Barlow、Jonas Y. Buser、Hendrik Glauninger、Carla V. Luciani、Joseph R. Martinelli、Niall Oram、Nichole Thompson‐Van Hook、Jeffery Richardson

  DOI：10.1002/adsc.201800167

  日期：2018.7.16

  moieties, but methods for their preparation typically possess numerous inefficiencies. Presented here is a methodology for the two‐step, one pot preparation of unsymmetrical stilbenes via sequential Heck reactions. The first Heck reaction with ethylene gas was analysed as a function of temperature and pressure for electronically differentiated naphthyl bromides and model‐aided reaction optimization was utilized

  丁苯酯是重要且有用的结构部分，但是其制备方法通常具有许多低效的地方。这里介绍的是一种通过连续的Heck反应分两步，一锅制备不对称丁苯甲醚的方法。对于电子分化的萘基溴化物，分析了乙烯气体的第一个Heck反应与温度和压力的关系，并利用模型辅助的反应优化来定义系统。此外，reactNMR用于确定乙烯在可用于Heck反应的普通有机溶剂中的溶解度。最终，开发了优化的顺序Heck反应工艺并将其应用于多种底物，从而可以有效制备不对称的对苯二甲酸酯，包括天然抗氧化剂，紫檀二烯。
• The Photochemical Cyclodehydrogenation Route to Polycyclic Azaarenes
  作者：Michael Hewlins、Rhys Salter

  DOI：10.1055/s-2007-983745

  日期：——

  paper reports an investigation of photochemical cyclodehydrogenation for the preparation of polycyclic azaarenes. Various naphthoquinolines and naphthoisoquinolines were obtained from 2-, 3-, and 4-[2-(1- and 2-naphthyl)vinyl]pyridine. 4-[2-(3-Phenanthryl)vinyl]pyridine gave pyreno[1,10- HIJ]isoquinoline. An efficient preparation of (2-arylvinyl)pyridines is described.

  本文报道了光化学环化脱氢制备多环氮杂芳烃的研究。从 2-、3- 和 4-[2-(1- 和 2-萘基)乙烯基]吡啶获得各种萘喹啉和萘异喹啉。4-[2-(3-菲基)乙烯基]吡啶得到芘[1,10-HIJ]异喹啉。描述了 (2-芳基乙烯基) 吡啶的有效制备方法。
• Palladium-Catalyzed Dehydrative Heck Olefination of Secondary Aryl Alcohols in Ionic Liquids: Towards a Waste-Free Strategy for Tandem Synthesis of Stilbenoids
  作者：Rakesh Kumar、Amit Shard、Richa Bharti、Yogesh Thopate、Arun Kumar Sinha

  DOI：10.1002/anie.201107261

  日期：2012.3.12

  All in one: A tandem strategy has been developed wherein secondary aryl alcohols are directly coupled with aryl halides to provide stilbenoids through a dehydrative Heck sequence in the ionic liquid [hmim]Br, and with water as a by‐product under microwave irradiation (see scheme). Classical methods do not permit this sequence to proceed in one pot, and some methods require multiple steps. hmim=1‐n

  总而言之：已开发了一种串联策略，其中仲芳基醇直接与芳基卤化物偶合，以通过离子液体[hmim] Br中的脱水Heck序列提供二苯乙烯类化合物，并在微波辐射下与水作为副产物（参见方案）。经典方法不允许此序列在一个锅中进行，并且某些方法需要多个步骤。hmim = 1 - n-己基-3-甲基咪唑鎓。
• Tryptophan 2,3-Dioxygenase (TDO) Inhibitors. 3-(2-(Pyridyl)ethenyl)indoles as Potential Anticancer Immunomodulators
  作者：Eduard Dolušić、Pierre Larrieu、Laurence Moineaux、Vincent Stroobant、Luc Pilotte、Didier Colau、Lionel Pochet、Benoît Van den Eynde、Bernard Masereel、Johan Wouters、Raphaël Frédérick

  DOI：10.1021/jm2006782

  日期：2011.8.11

  Tryptophan catabolism mediated by indoleamine 2,3-dioxygenase (IDO) is an important mechanism of peripheral immune tolerance contributing to tumoral immune resistance. IDO inhibition is thus an active area of research in drug development. Recently, our group has shown that tryptophan 2,3-dioxygenase (TDO), an unrelated hepatic enzyme also catalyzing the first step of tryptophan degradation, is also expressed in many tumors and that this expression prevents tumor rejection by locally depleting tryptophan. Herein, we report a structure- activity study on a series of 3-(2-(pyridyl)ethenyl)indoles. More than 70 novel derivatives were synthesized, and their TDO inhibitory potency was evaluated. The rationalization of the structure-activity relationships (SARs) revealed essential features to attain high TDO inhibition and notably a dense H-bond network mainly involving His(55) and Thr(254) residues. Our study led to the identification of a very promising compound (58) displaying good TDO inhibition (K-i = 5.5 mu M), high selectivity, and good oral bioavailability. Indeed, 58 was chosen for preclinical evaluation.
• Masetti, Fausto; Bartocci, Giampiero; Mazzucato, Ugo, Gazzetta Chimica Italiana, 1982, vol. 112, # 7/8, p. 255 - 260
  作者：Masetti, Fausto、Bartocci, Giampiero、Mazzucato, Ugo、Galiazzo, Guido

  DOI：——

  日期：——