cinnamil | 65644-29-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: cinnamil
• 英文别名: 1,6-diphenyl-hexa-1,5-diene-3,4-dione；1,6-Diphenylhexa-1,5-diene-3,4-dione
• CAS: 65644-29-3
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: XCFBXZJFMURWRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenyl-5H-[1,2,3]-oxathiazole 2,2-dioxide 、 cinnamil 在 三乙烯二胺 作用下， 以 neat (no solvent) 为溶剂， 反应 0.67h， 以79%的产率得到2-cinnamoyl-4,6-diphenylpyridine
  参考文献：
  名称：

  无金属和无溶剂方法通过环状氨基磺酸亚胺与β，γ-不饱和α-酮羰基的多米诺反应进行取代的吡啶甲酸酯

  摘要：

  在DABCO促进的MW辐射下，在纯净条件下，开发了5/6元环状氨基磺酸亚胺与各种β，γ-不饱和α-酮羰基化合物的高效，无溶剂，生态友好的多米诺反应，该反应是由DABCO促进的，作为固体有机碱用于快速构建新型的高密度官能化的吡啶甲酸类化合物。这种有趣的无金属溶剂策略可在芳基环上提供多种有用的功能，并能在较短的时间间隔（20-40分钟）内，将上述氮杂杂环化合物的收率很好地提高。通过我们独特的方法成功合成了具有生物学前途的咪唑并[1,2- a ]吡啶。

  DOI：

  10.1021/acs.joc.7b01792
• 作为产物：
  描述：

  苯甲醛 、 2,3-丁二酮 在 哌啶 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 cinnamil
  参考文献：
  名称：

  一种涉及 Huisgen 两性离子合成双吡唑啉和高度官能化吡唑啉的新方案

  摘要：

  本工作说明了通过三苯基膦介导的肉桂与偶氮二羧酸二烷基酯反应合成双吡唑啉的新方法。此外，通过用三苯基膦和偶氮酯处理 2-alkenyl-1,3-diones 完成了高度官能化的吡唑啉衍生物的合成。

  DOI：

  10.1016/j.tetlet.2022.154059

文献信息

• Bipiridine derivative and organic electroluminescence element containing the same
  申请人：Yamagata Promotional Organization for Industrial Technology

  公开号：EP2275409A1

  公开（公告）日：2011-01-19

  The present invention provides a new bipyridine derivative which is suitable for an electron transport material of an organic electronics element and which has bipyridyl central rings as a core, and further provides an organic electroluminescence element containing the derivative. The bipyridine derivative is expressed by the following general formula. (where A1, A2: represent an aromatic heterocyclic group (except for a carbazolyl group) and an aromatic hydrocarbon group and the aromatic heterocyclic group may be combined; a, b = 1 or 2; Ar1, Ar2: represent a divalent or trivalent aromatic hydrocarbon group which may be substituted by hydrogen atom, an alkyl group, a cycloalkyl group, or an alkoxy group; B1, B2: represent hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, an aromatic hydrocarbon group, or an aromatic heterocyclic group; and ring E1, ring E2: represent a pyridine ring, and may have hydrogen atom, an alkyl group, a cycloalkyl group, or an alkoxy group.), which is used as an electron transport material.

  本发明提供了一种新的联吡啶衍生物，适用于有机电子元件的电子传输材料，并且具有联吡啶中心环作为核心，并进一步提供了含有该衍生物的有机电致发光元件。联吡啶衍生物由以下一般公式表示（其中A1、A2：代表芳香杂环基团（除了吲哚基团）和芳香烃基团，芳香杂环基团可以结合；a，b = 1或2；Ar1，Ar2：代表可由氢原子、烷基、环烷基或烷氧基取代的二价或三价芳香烃基团；B1，B2：代表氢原子、烷基、环烷基、烷氧基、芳香烃基团或芳香杂环基团；环E1，环E2：代表吡啶环，并且可以具有氢原子、烷基、环烷基或烷氧基）。该衍生物用作电子传输材料。
• Simple and Convenient Approach to the Kr€ohnke Pyridine Type Synthesis of Functionalized Indol-3-yl Pyridine Derivatives Using 3-Cyanoacetyl Indole
  作者：Prakasam Thirumurugan、A. Nandakumar、D. Muralidharan、Paramasivan T. Perumal

  DOI：10.1021/cc9001394

  日期：2010.1.11

  Access to privileged heterocyclic scaffolds involving 4-aryl-6-(1H-indol-3-yl)-2,2-bipyridine-5-carbonitriles and 6-(2-furyl)-2-(1H-indol-3-yl)-4-arylpyridine-3-carbonitriles frameworks has been achieved via a single-step multicomponent reaction of structurally diverse aldehydes, 2-acetylpyridine (or) 2-acetylfuran and 3-cyanoacetyl indole in ammonium acetate under neat condition. Also a series of

  获得涉及4-芳基-6-（1 H-吲哚-3-基）-2,2-联吡啶-5-腈和6-（2-呋喃基）-2-（1 H-吲哚-3 ）的特权杂环支架通过在纯净条件下在乙酸铵中进行结构多样的醛，2-乙酰基吡啶（或）2-乙酰基呋喃和3-氰基乙酰基吲哚的单步多组分反应，已获得了-yl）-4-芳基吡啶-3-腈骨架。也是一系列的6,6'-二（1 H-吲哚-3-基）-4,4'-二芳基-2,2'-联吡啶-5,5'-二甲腈和7,7,7'，7 '-四甲基-4,4'-双（芳基）-4,6,7,8,4'，6'，7'，8'-八氢-1 H，1 H- [2,2']联喹啉基- 5,5'-二酮衍生物是使用肉桂醇，3-氰基乙酰基吲哚（或）二甲基酮和乙酸铵合成的。
• Synthesis of 2,5-diphenyl-3,4-di(phenylethenyl)cyclopentadienone, -pyrrole and -thiophene
  作者：Syeda Shaista Gillani Syeda Shaista Gillani、Munawar Ali Munawar Munawar Ali Munawar、Hafiz Adnan Ahmad Hafiz Adnan Ahmad、Rabia Babar Rabia Babar、Khalid Mohammed Khan Khalid Mohammed Khan、Jamil Anwar Chaudhary Jamil Anwar Chaudhary

  DOI：10.52568/001028/jcsp/44.03.2022

  日期：——

  2,5-Diphenyl-3,4-di(phenylethenyl)cyclopentadienone (2), -pyrrole (3), and -thiophene (4) have been synthesized by bi-steps strategy. Step one involves the synthesis of cinnamil (1) by the condensation of 2,3-butanedione with benzaldehyde in the presence of Pyrrolidine as a catalyst. Step two involves the synthesis of 2,5-diphenyl-3,4-di(phenylethenyl)cyclopentadienone (2), -pyrrole (3), and -thiophene (4) by the condensation of cinnamil (1) with dibenzyl ketone, dibenzylamine, and dibenzyl sulfide, respectively in the presence of sodium hydride (base) and methylene chloride (solvent) while stirring. 1HNMR, LC-MS, IR, UV-visible, and fluorescence spectroscopy were used to confirm these products (2-4). Our method facilitated the proficient installation of four various groups on the cyclopentadienone (2), pyrrole (3), and thiophene (4) rings in two steps with an extended conjugated framework.

  我们采用两步法合成了 2,5-二苯基-3,4-二(苯基乙烯基)环戊二烯酮 (2)、吡咯 (3) 和噻吩 (4)。第一步是在吡咯烷作为催化剂的情况下，通过 2,3-丁二酮与苯甲醛的缩合合成肉桂醛（1）。第二步是在氢化钠（碱）和二氯甲烷（溶剂）的存在下，通过肉桂苯（1）与二苄基酮、二苄胺和二苄基硫醚的缩合，在搅拌下分别合成 2,5-二苯基-3,4-二（苯基乙烯基）环戊二烯酮（2）、-吡咯（3）和-噻吩（4）。使用 1HNMR、LC-MS、IR、UV-Visible 和荧光光谱确认了这些产物 (2-4)。我们的方法有助于通过两个步骤在环戊二烯酮（2）、吡咯（3）和噻吩（4）环上熟练地安装四个不同的基团，并形成一个扩展的共轭框架。
• Efficient Cu(OTf) 2 -catalyzed and microwave-assisted rapid synthesis of 3,4-fused chromenopyridinones under neat conditions
  作者：Anubha Yadav、Soumen Biswas、Shaikh M. Mobin、Sampak Samanta

  DOI：10.1016/j.tetlet.2017.08.006

  日期：2017.9

  An efficient, solvent-free, environmentally benign, Cu(OTf)(2)-catalyzed and microwave-assisted fast synthesis of a fascinating class of a number of angularly fused chromenopyridinones having a carboxylate group at C-2 position on the pyridine ring via a one-pot [3+3] annulation reaction of several aminocoumarins/cyclic beta-enaminones with different kinds of gamma-aryI/styryI/heteroaryl-substituted-beta,gamma-unsaturated alpha-ketoesters as Michael acceptors under open atmosphere. This eco-friendly method delivers good to excellent yields of pyridine-fused-heterocycles within (15-40 min) without using any traditional oxidants and allows several important functionalities. Furthermore, by this method, stereos elective synthesis of trans-7,8-diaryl-8.9-dihydrochromeno[4,3-b]cyclopenta[e]pyridine-6,10-diones were obtained in an excellent diastereoselective manner (dr <= 99:1). (C) 2017 Elsevier Ltd. All rights reserved.
• A simple one-pot synthesis of functionalised 6-(indol-3-yl)-2,2′-bipyridine derivatives via multi-component reaction under neat condition
  作者：Prakasam Thirumurugan、Paramasivan T. Perumal

  DOI：10.1016/j.tetlet.2009.04.121

  日期：2009.7

  A series of 4-aryl-6-(1H-indol-3-yl)-2,2-bipyridine-5-carbonitrile derivatives were synthesized via a one-pot multi-component reaction of aromatic aldehydes, 3-(cyanoacetyl)indole and 2-acetyl pyridine in ammonium acetate by conventional heating and microwave irradiation under solvent-free condition. Also a series of 6,6'-di(1H-indol-3-yl)-4,4'-diaryl-2,2'-bipyridine-5,5'-dicarbonitrile derivatives were synthesized using cinnamils, 3-(cyanoacetyl)indole and ammonium acetate. The methodology affords high yields of product at short reaction time. (C) 2009 Elsevier Ltd. All rights reserved.