but-3-yne-1,1-diyldibenzene | 4286-87-7

• 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: but-3-yne-1,1-diyldibenzene
• 英文别名: 4,4-Diphenyl-1-butyne；1-phenylbut-3-ynylbenzene
• CAS: 4286-87-7
• 化学式: C₁₆H₁₄
• 分子量: 206.287
• InChiKey: QCZWQVNQVSWELF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  but-3-yne-1,1-diyldibenzene 在 potassium superoxide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.5h， 以87%的产率得到1,1-二苯基-1,3-丁二烯
  参考文献：
  名称：

  Superoxide mediated isomerization of 4-aryl-but-1-ynes to 1-aryl-1,3-butadienes

  摘要：

  A new role of superoxide ion in the isomerization of homobenzylic acetylenes leading to 1-aryl-1,3-butadienes is reported. The unconventional reagent 1(02 is found to be superior in performing this kind of isomerization over other the commonly used bases. For substrates containing arene moiety and triple bond connected through more than two methylene groups, and for propargylcyclohexanol the reagent selectively effected migration of the triple bond. Reactivity of 1(02 towards the substrates having disubstitution at benzylic position varied depending on the nature of the substitution, alkyl-substitution lead to isomerization to give mixture of allene (an intermediate in the isomerization of acetylene to 1,3-butadiene) and triple bond migration product; whereas phenyl-substituted compound gave 1,3-diene. The utility of the methodology was demonstrated through a Diels-Alder reaction of one of the dienes obtained by the isomerization with suitable dienophiles. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.075
• 作为产物：
  描述：

  (2-溴乙烷-1,1-二基)二苯 在 1,1-二溴乙烷 、 potassium carbonate 、 magnesium 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 3.0h， 生成 but-3-yne-1,1-diyldibenzene
  参考文献：
  名称：

  具有反式烯烃间隔基作为强效GABA吸收抑制剂的新型N-取代的苯甲酸衍生物的合成和生物学评估

  摘要：

  我们的研究提出的合成和结构-活性关系密切相关DDPM-1457 [（新颖的N-取代哌啶甲酸衍生物（SAR）小号） -图2a ]中，（a化学稳定的模拟小号）-SNAP-5114（1）为了寻找新的有效的mGAT4选择性抑制剂。亚胺离子化学是制备所需的，新的N-取代的庚酸衍生物的关键步骤，该新的N-取代的庚酸衍生物含有通过反烯烃间隔基连接到该庚酸部分的各种不同的杂环。根据目标化合物对GABA转运蛋白mGAT1-mGAT4的效价和亚型选择性，对目标化合物进行了表征。

  DOI：

  10.1016/j.bmc.2018.11.002

文献信息

• Synthesis of Allene Substituted Nipecotic Acids by Allenylation of Terminal Alkynes
  作者：Maren Schaarschmidt、Klaus T. Wanner

  DOI：10.1021/acs.joc.7b00630

  日期：2017.8.18

  several secondary amines serving as hydride donors in propargylic amines undergoing a [1,5]-hydride transfer reaction to yield the respective terminal and 1,3-disubstituted allenes were studied. For this study, a two-step procedure was employed. At first, the synthesis of propargylic amines via the CuI-catalyzed aldehyde-alkyne-amine reactions (A3 coupling) was accomplished. The obtained propargylic amines

  研究了进行[1,5]-氢化物转移反应生成相应的末端和1,3-二取代的烯丙基的炔丙基胺中用作氢化物供体的几种仲胺的相对反应性。对于本研究，采用了两步程序。首先，通过Cu I催化的醛-炔-胺反应（A 3偶联）完成了炔丙基胺的合成。随后将获得的炔丙基胺在CdI 2或ZnI 2催化下转化为所需的烯丙基。结果，在所使用的各种仲胺中，在空间体积，电子性质和构象性质方面不同，烯丙基（叔）发现叔丁基胺是合成末端亚丙基的最佳氢化物供体。为了合成1，3-二取代的烯，在炔丙基位置含有烯丙基（叔丁基）胺或1,2,3,6-四氢吡啶单元的丙炔衍生物表现最佳。最后，通过改进的方法，使用ZnI 2作为催化剂来制备1-取代的CdI 2或CdI 2来合成1,3-二取代的烯，以高收率合成了含有N-烯基取代基的庚二酸衍生物。
• Kuznetsov,S.G.; Libman,N.M., Journal of Organic Chemistry USSR (English Translation), 1965, vol. 1, p. 1418 - 1424
  作者：Kuznetsov,S.G.、Libman,N.M.

  DOI：——

  日期：——
• Superoxide mediated isomerization of 4-aryl-but-1-ynes to 1-aryl-1,3-butadienes
  作者：Faiz Ahmed Khan、Basavaraj M. Budanur

  DOI：10.1016/j.tet.2015.07.075

  日期：2015.10

  A new role of superoxide ion in the isomerization of homobenzylic acetylenes leading to 1-aryl-1,3-butadienes is reported. The unconventional reagent 1(02 is found to be superior in performing this kind of isomerization over other the commonly used bases. For substrates containing arene moiety and triple bond connected through more than two methylene groups, and for propargylcyclohexanol the reagent selectively effected migration of the triple bond. Reactivity of 1(02 towards the substrates having disubstitution at benzylic position varied depending on the nature of the substitution, alkyl-substitution lead to isomerization to give mixture of allene (an intermediate in the isomerization of acetylene to 1,3-butadiene) and triple bond migration product; whereas phenyl-substituted compound gave 1,3-diene. The utility of the methodology was demonstrated through a Diels-Alder reaction of one of the dienes obtained by the isomerization with suitable dienophiles. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of novel N-substituted nipecotic acid derivatives with a trans-alkene spacer as potent GABA uptake inhibitors
  作者：Krisztián Tóth、Georg Höfner、Klaus T. Wanner

  DOI：10.1016/j.bmc.2018.11.002

  日期：2018.12

  study presents the synthesis and structure-activity relationship (SAR) of novel N-substituted nipecotic acid derivatives closely related to DDPM-1457 [(S)-2a], a chemically stable analog of (S)-SNAP-5114 (1), in the pursuit of finding new and potent mGAT4 selective inhibitors. Iminium ion chemistry served as key step for the preparation of the desired, new N-substituted nipecotic acid derivatives containing

  我们的研究提出的合成和结构-活性关系密切相关DDPM-1457 [（新颖的N-取代哌啶甲酸衍生物（SAR）小号） -图2a ]中，（a化学稳定的模拟小号）-SNAP-5114（1）为了寻找新的有效的mGAT4选择性抑制剂。亚胺离子化学是制备所需的，新的N-取代的庚酸衍生物的关键步骤，该新的N-取代的庚酸衍生物含有通过反烯烃间隔基连接到该庚酸部分的各种不同的杂环。根据目标化合物对GABA转运蛋白mGAT1-mGAT4的效价和亚型选择性，对目标化合物进行了表征。