(2-(phenylethynyl)phenyl)methanamine | 38379-22-5

• 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-(phenylethynyl)phenyl)methanamine
• 英文别名: 2-(2-Phenylethynyl)benzenemethanamine；[2-(2-phenylethynyl)phenyl]methanamine
• CAS: 38379-22-5
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: PKTFIZHUBHFEGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 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：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-(phenylethynyl)phenyl)methanamine 在 4-二甲氨基吡啶 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 cesium acetate 、 copper diacetate 、 N,N'-二环己基碳二亚胺 作用下， 以 2-甲基-2-丁醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  铑（III）通过C–H活化催化分子内环化：罗塞他汀和羟帕马汀的简明合成

  摘要：

  报道了一种柔性且有效的铑（III）催化的带有链状炔烃的苯甲酰胺的分子内环化反应，用于合成吲哚嗪酮和喹啉酮。该反应显示出较宽的底物范围和优异的官能团耐受性，包括不同种类的杂环底物，例如呋喃，噻吩，吡咯，苯并呋喃，苯并噻吩，吲哚和异烟酰胺底物。该方法还提供了一种合成罗塞他汀和羟帕马汀的实用而有效的方法。

  DOI：

  10.1039/c7cc06860c
• 作为产物：
  描述：

  (E)-2-bromostilbene 在 吡啶 、 lithium aluminium tetrahydride 作用下， 生成 (2-(phenylethynyl)phenyl)methanamine
  参考文献：
  名称：

  Antiarrhythmic agents. 2-, 3-, and 4-Substituted benzylamines

  摘要：

  The synthesis of a series of 2-, 3-, and 4-substituted benzylamine derivatives is described. These compounds were studied for their effect on experimental cardiac arrhythmias. Many of the derivatives, but in particular 2-(p-methoxyphenylethynyl)benzylamine (3d), alpha,alpha-dimethyl-4y(phenylethynyl)benzylamine (7a), and alpha,alpha-dimethyl-4-phenethylbenzylamine (12g), showed good antiarrhythmic activity.

  DOI：

  10.1021/jm00236a006

文献信息

• Synthesis of Pyrrolo[1,2-<i>b</i>]isoquinolines via Gold(I)-Catalyzed Cyclization/Enyne Cycloisomerization/1,2-Migration Cascade
  作者：Liangliang Song、Guilong Tian、Luc Van Meervelt、Erik V. Van der Eycken

  DOI：10.1021/acs.orglett.0c02310

  日期：2020.8.21

  of the migrating group is comprehensively investigated. The study of the mechanism indicates that the pathway involving a gold carbenoid species is the main pathway and that the 1,2-migration of alkyl and aryl groups to the gold carbenoid occurs in an intramolecular fashion. This cascade reaction is also employed as the key step for the synthesis of a decumbenine B analogue.

  开发了金（I）催化的N-炔基2-乙酰胺的级联转化，用于快速有效地合成吲哚并立定支架。通过顺序的亲核环化/烯炔环异构化/ 1,2-迁移过程，各种吡咯并[1,2- b]异喹啉在温和条件下以区域特异性和会聚的方式获得。在此过程中可以耐受各种烷基和芳基迁移基团。全面研究了迁移组的电子效应。对机理的研究表明，涉及金类胡萝卜素的途径是主要途径，并且烷基和芳基的1，2-迁移以分子内方式发生。该级联反应也被用作合成癸二烯B类似物的关键步骤。
• Copper-catalyzed trifluoromethylazidation and rearrangement of aniline-linked 1,7-enynes: access to CF₃-substituted azaspirocyclic dihydroquinolin-2-ones and furoindolines
  作者：Liu-Zhu Yu、Yin Wei、Min Shi

  DOI：10.1039/c7cc04748g

  日期：——

  A set of reactions involving copper-catalyzed trifluoromethylazidation and then rearrangement of aniline-linked 1,7-enynes with the relatively poorly reactive Togni reagent I and TMSN3 was developed, and provided facile access to structurally diverse and useful CF3-substituted azaspirocyclic dihydroquinolin-2-ones bearing two adjacent quaternary carbon centers. We were also able to obtain these products

  开发了一套反应，涉及铜催化的三氟甲基叠氮化，然后用相对较差的反应性Togni试剂I和TMSN 3进行苯胺连接的1,7-烯炔的重排，并提供了易于获得的结构多样且有用的CF 3取代的氮杂螺环二氢喹啉的途径。带有两个相邻的季碳中心的-2-ones。我们也能够大规模获得这些产品。此外，将获得的产物在被NaBH 4还原后，进一步转化为一系列具有三个连续的季碳中心的具有合成价值的呋喃二氢吲哚。另外，由于醇解和LiAlH 4的作用，提供了多功能化的氮丙啶-还原相应的二氢喹啉-2-酮2ba证明了该新开发方案的合成价值。
• Thermal Cyclization of Nonconjugated Aryl-Yne-Carbodiimide Furnishing a Dibenzonaphthyridine Derivative
  作者：Hidenori Kimura、Kohei Torikai、Ikuo Ueda

  DOI：10.1248/cpb.57.393

  日期：——

  The reagent-free C2–C7 thermal cyclization of a nonconjugated aryl–yne–carbodiimide yielded a dibenzo[b,g][1,8]naphthyridine derivative, whose congeners are known to possess fascinating pharmacological properties. This is the first heteroaromatic compound prepared by the thermal cycloaromatization of “nonconjugated” aryl–ynes.

  通过非共轭芳基炔-碳二亚胺的无试剂 C2-C7 热环化反应，制备出了一种二苯并[b,g][1,8]萘啶衍生物，其同系物具有令人着迷的药理特性。这是首个通过 "非共轭 "芳炔的热环化反应制备的杂芳香族化合物。
• Cyclization reactions of 2-alkynylbenzyl alcohol and 2-alkynylbenzylamine derivatives promoted by tetrabutylammonium fluoride
  作者：Kou Hiroya、Rumi Jouka、Mitsuyoshi Kameda、Akito Yasuhara、Takao Sakamoto

  DOI：10.1016/s0040-4020(01)00991-7

  日期：2001.11

  The regioselectivity of the cyclization reaction of 2-ethynylbenzyl alcohol and 2-ethynylbenzylamine derivatives promoted by TBAF was investigated. Six-membered ring derivatives were obtained from the compounds, which have a butyl group on the triple bond. Whereas five-membered ring products were afforded from the substrates having hydrogen or aromatic substituents. on the acetylene moiety. It was also concluded that both the tetrabutylammonium cation and fluoride anion were essential for the cyclization. Thus, the actual mechanism and catalytic cycle were also suggested. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Highly Selective Construction of Medium-Sized Lactams by Palladium-Catalyzed Intramolecular Hydroaminocarbonylation of Aminoalkynes
  作者：Yue Hu、Hanmin Huang

  DOI：10.1021/acs.orglett.7b02284

  日期：2017.10.6

  A novel palladium-catalyzed intramolecular hydro-aminocarbonylation of aminoalkynes has been developed. This direct and operationally simple protocol provides a rapid and reliable approach to a diverse array of valuable seven- and eight-membered lactams with high chemoselectivity and regioselectivity. The high selectivity might be attributed to rational tuning the electronic nature of the amine moiety and the palladium catalyst, which enabled this transformation to proceed in the absence of acidic or any other additives under fairly mild reaction conditions. This method paves the way for the synthesis of medium-sized lactams.