trans 4-(2-thien-2-yl-ethenyl)pyridine | 66417-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: trans 4-(2-thien-2-yl-ethenyl)pyridine
• 英文别名: 4-[(E)-2-thien-2-ylethenyl]pyridine；(E)-4-(2-(thiophen-2-yl)vinyl)pyridine；trans-1-(4-pyridyl)-2-(2-thienyl)ethylene；pte；4-(2-thiophen-2-yl-vinyl)-pyridine；4-[2-(2-Thienyl)ethenyl]pyridine；4-[(E)-2-thiophen-2-ylethenyl]pyridine
• CAS: 66417-75-2
• 化学式: C₁₁H₉NS
• 分子量: 187.265
• InChiKey: JADQXNQBEASRFB-ONEGZZNKSA-N

物化性质

• 沸点：
  318.3±11.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans 4-(2-thien-2-yl-ethenyl)pyridine 在 四(三苯基膦)钯 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 6.33h， 生成 1-{5-[1-(4-N-methylpyridinium)ethen-2-yl]thien-2-yl}-2-[5-(dicyanomethanido)thien-2-yl]ethylene
  参考文献：
  名称：

  Facile, Regioselective Synthesis of Highly Solvatochromic Thiophene-Spaced N-Alkylpyridinium Dicyanomethanides for Second-Harmonic Generation

  摘要：

  The facile and clean synthesis of a navel class of highly solvatochromic chromophores 1 is reported. Compounds 1 are push-pull systems containing a negatively charged dicyanomethanide as a donor group and a positively charged N-alkylpyridinium as an acceptor group. The terminal polar functions are spaced by a thiophene-based moiety containing one or two heterocyclic rings and none, one, or two ethylene bridges. Chromophores 1 have been obtained through a general synthetic scheme involving, as the last step, the 100% regioselective alkylation of the precursor bidentate anions 2, where two competing nucleophilic sites, one neutral at the pyridic nitrogen and one anionic at the carbanionic carbon of the dicyanomethanide group, are present. The unprecedented highly regioselective attack of the alkylating agent onto the neutral pyridic nitrogen rather than the highly charged carbanionic carbon has been also confirmed in the case of the intermolecular competition. Multinuclear (C-13 and N-15) NMR spectroscopy has been used to investigate the structure and the extent of intramolecular charge transfer in 1, which are shown to exist in the ground state as highly charge-separated zwitterionic systems. Experimental results are discussed and compared with semiempirical (PM3) computations. The solvatochromic response of compounds 1, among the highest ever reported in the literature for similar systems, candidates this class of compounds as very attractive active components of nonlinear optical materials.

  DOI：

  10.1021/jo970059x
• 作为产物：
  描述：

  4-((benzenesulfonyl)methyl)pyridine 、 2-噻吩甲醇 在 sodium hydride 作用下， 以 mineral oil 为溶剂， 反应 19.0h， 以59%的产率得到trans 4-(2-thien-2-yl-ethenyl)pyridine
  参考文献：
  名称：

  (E)-Specific direct Julia-olefination of aryl alcohols without extra reducing agents promoted by bases

  摘要：

  芳基醇的(E)-特异性直接Julia烯烃化反应在碱的促进下进行：一种自氢化物转移氧化还原过程的策略。

  DOI：

  10.1039/c5cc01965f

文献信息

• Molecular size and flexibility as determinants of selectivity in the oxidation of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analogs by monoamine oxidase A and B
  作者：S. M. N. Efange、R. H. Michelson、A. K. Tan、M. J. Krueger、T. P. Singer

  DOI：10.1021/jm00061a020

  日期：1993.4

  In the present study, a number of isomeric 4-naphthyl-, 4-(naphthylalkyl)-, 4-thienyl-, and 4-(thienylalkyl)tetrahydropyridines, conformationally restrained and flexible analogs of MPTP, were synthesized and evaluated as potential selective substrates of MAO A and B. In terms of the parameter (turnover number)/Km, the bulky naphthyl analogs were invariably better substrates of MAO A than kynuramine

  在1-甲基-4-苯基-1,2,3,6-四氢吡啶（MPTP）的苯基和四氢吡啶基部分之间引入亚甲基桥导致单胺氧化酶B（MAO B）的选择性比单胺氧化酶A（毛A）。然而，该桥的延长导致选择性的完全丧失。在本研究中，合成了多种异构的4-TPP的构象受限和灵活的类似物4-萘基-，4-（萘基烷基）-，4-噻吩基-和4-（噻吩基烷基）四氢吡啶，并将其评估为潜在的选择性底物就参数（周转数）/ Km而言，笨重的萘基类似物总是比该酶的参考底物Kynuramine更好的MAO A底物。此外，所有萘类似物，无论构象迁移率如何，同样，发现所有噻吩基类似物都是MAO B的更有效底物。与萘相反，构象受约束的噻吩9a和10a被认为是MAO B的较差底物，相对于苄胺，参考底物。这些结果表明，这些化合物对MAO A或B的选择性取决于分子大小和柔韧性的复杂相互作用。在这种相互作用中，这两个因素之一可能占主导地位。这些结果表明，这些化合物对MAO
• ALPHA-SYNUCLEIN LIGANDS
  申请人：Washington University

  公开号：US20170189566A1

  公开（公告）日：2017-07-06

  The present invention generally relates to various compounds that are useful as α-synuclein ligands. The invention further relates to methods of using these compounds and their radiolabeled analogs for the detection of synucleinopathies, including Parkinson's disease (PD).

  本发明通常涉及作为α-突触核蛋白配体有用的各种化合物。该发明进一步涉及使用这些化合物及其放射标记类似物用于检测突触核蛋白病，包括帕金森病（PD）的方法。
• Heck reaction with heteroaryl halides in the presence of a palladium-tetraphosphine catalyst
  作者：Florian Berthiol、Marie Feuerstein、Henri Doucet、Maurice Santelli

  DOI：10.1016/s0040-4039(02)01109-7

  日期：2002.8

  cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C3H5)]2 system catalyses efficiently the Heck reaction of heteroaryl halides with n-butyl acrylate, styrene, vinylpyridine and vinyl ether derivatives. High turnover numbers can be obtained for the reactions with halo pyridines, quinolines, furans or thiophenes.

  顺式，顺式，顺式-1,2,3,4-四（二苯基膦甲基）环戊烷/ [PdCl（C3H5）] 2系统有效地催化杂芳基卤化物与丙烯酸正丁酯，苯乙烯，乙烯基吡啶和乙烯基醚衍生物的Heck反应。与卤代吡啶，喹啉，呋喃或噻吩的反应可获得较高的转化率。
• Facile Synthesis of Thienoquinolines and Thienoisoquinolines via Photocyclization
  作者：A. L. Marzinzik、P. Rademacher

  DOI：10.1055/s-1995-4062

  日期：1995.9

  A synthetic route starting from diethyl thenylphosphonates offers a facile and efficient method for the preparation of new isomeric thienoquinolines and thienoisoquinolines. Their structure and heteronuclear connectivity information was unambiguously established by analysis of NMR data using CH COSY and HMBC techniques.

  以二乙基膦酸盐为起点的合成路线为制备新的异构噻吩喹啉和噻吩异喹啉提供了一种简便高效的方法。通过使用 CH COSY 和 HMBC 技术分析核磁共振数据，明确地确定了它们的结构和异核连接信息。
• Single-Crystal-to-Single-Crystal [2 + 2] Photodimerization Involving B←N Coordination with Generation of a Thiophene Host
  作者：Gonzalo Campillo-Alvarado、Changan Li、Zhiting Feng、Kristin M. Hutchins、Dale C. Swenson、Herbert Höpfl、Hugo Morales-Rojas、Leonard R. MacGillivray

  DOI：10.1021/acs.organomet.0c00258

  日期：2020.6.22

  monotopic B←N adducts composed of a phenylboronic acid catechol ester and an alkene with a terminal thiophene group. The photoreaction generates a ditopic B-adduct involving a head-to-tail cyclobutane regio- and stereoselectively. The photodimerization is accompanied by an increase in the tetrahedral character of the B atom. The resulting boron enables channel confinement of chloroform upon recrystallization

  我们报道了B←N配位，以支持固态的单晶至单晶反应。[2 + 2]光二聚反应是通过面对面的π-堆叠单峰B←N加合物实现的，该峰由苯基硼酸邻苯二酚酯和带有末端噻吩基团的烯烃组成。光反应产生对位和立体选择性的头到尾环丁烷的对位B加合物。光二聚化伴随着B原子的四面体特征的增加。所得到的硼在重结晶时能使氯仿通道受限。