(Z)-1,3,4,6-tetraphenyl-3-hexene-1,5-diyne | 58593-93-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (Z)-1,3,4,6-tetraphenyl-3-hexene-1,5-diyne
• 英文别名: (Z)-1,3,4,6-tetraphenyl-3-hexen-1,5-diyne；1,3,4,6-tetraphenylhex-3Z-en-1,5-diyne；1,3,4,6-Tetraphenyl-3-hexen-1,5-diyn；[(Z)-1,4,6-triphenylhex-3-en-1,5-diyn-3-yl]benzene
• CAS: 58593-93-4
• 化学式: C₃₀H₂₀
• 分子量: 380.489
• InChiKey: ZYBGGNWWIBXKDJ-FLWNBWAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (Z)-1,3,4,6-tetraphenyl-3-hexene-1,5-diyne 以 正己烷 、 丙酮 为溶剂， 以60%的产率得到(E)-1,3,4,6-tetraphenyl-3-hexene-1,5-diyne
  参考文献：
  名称：

  Alkynylzirconation of Alkynes and Application to One-Pot Bisalkynylation of Alkynes

  摘要：

  Stereocontrolled alkynylzirconation of unactivated alkynes was achieved by the reaction of an alkyne with Cp2ZrEt2 and alkynyl halide in this order. After hydrolysis of the alkynylzirconation product, trisubstituted enyne derivatives were obtained in good yields. Functionalized enynes were also prepared by the reaction of the alkynylzirconation products with a variety of electrophiles. Subsequent addition of the second alkynyl halide to the alkynylzirconation products provided an in situ protocol for bisalkynylation of alkynes into (Z)-enediynes in good yields.

  DOI：

  10.1021/jo026037e
• 作为产物：
  描述：

  1,3-diphenyl-1-propyne 在 正丁基锂 作用下， 以 正己烷 、 苯 为溶剂， 反应 3.5h， 生成 (Z)-1,3,4,6-tetraphenyl-3-hexene-1,5-diyne
  参考文献：
  名称：

  在1和3位被硒烯基取代的丙二烯的合成与反应性。

  摘要：

  1,3-双（甲基硒代）-和1,3-双（苄基硒代）-1,3-二苯基丙二烯是通过由1,3-二苯基丙炔和正丁基锂制备的Ph（2）C（3）二价阴离子反应合成的在TMEDA存在下，与二甲基二硒化物或苄基硒氰酸酯，二价阴离子与二甲基二硒化物和苄基硒氰酸酯的混合物反应，生成1-苄基硒基-3-甲基硒代烯以及对称的烯。通过使二价阴离子与相应的烷烃二硒氰酸酯反应，也获得了二硒环烯基和四硒环双烯基。1,3-双（烷基硒基）烯丙基的热反应主要通过自由基途径提供烯二炔，而九元环烯丙基则通过分子内重排提供分子内环化产物。加热环状双亚丙基烯得到衍生自分子内环化产物的化合物以及少量的烯二炔。辐照丙二烯导致亚硒基重排，生成炔烃，炔烃也发生光化学反应生成烯二炔。

  DOI：

  10.1021/jo001483s

文献信息

• Enediynes from Aza-Enediynes:  <i>C</i>,<i>N</i>-Dialkynyl Imines Undergo Both Aza-Bergman Rearrangement and Conversion to Enediynes and Fumaronitriles
  作者：Liping Feng、Aibin Zhang、Sean M. Kerwin

  DOI：10.1021/ol0600638

  日期：2006.5.1

  [reaction; see text] Aza-enediynes (C,N-dialkynyl imines) undergo thermal aza-Bergman rearrangement to beta-alkynyl acrylonitriles through 2,5-didehydropyridine (2,5-ddp) intermediates. Certain aza-enediynes also undergo an alternative process affording enediynes and fumaronitriles. Studies employing a specifically (l3)C-labeled aza-enediyne show that the conversion to enediyne is second order in aza-enediyne

  [反应; 见文本]氮杂二烯（C，N-二炔基亚胺）通过2，5-二氢吡啶（2，5-ddp）中间体进行热氮杂-Bergman重排，生成β-炔基丙烯腈。某些氮杂二烯炔也经历另一种过程，得到烯二炔和富马腈。使用特定的（13）C标记的氮杂二烯炔进行的研究表明，转化为烯二炔在氮杂二烯炔中是二阶的，通过“头对尾”偶联进行，并提供了（Z）-二烯炔。
• Synthesis and Thermal Reaction of 1,3-Bis(alkylseleno)allenes
  作者：Toshio Shimizu、Daisuke Miyasaka、Nobumasa Kamigata

  DOI：10.1021/ol0001158

  日期：2000.6.1

  Reactions of Ph(2)C(3) dianion, prepared from 1,3-diphenylpropyne and n-butyllithium, with dimethyl diselenide and benzylselenocyanate yielded 1,3-bis(methylseleno)-1,3-diphenylpropadiene and 1,3-bis(benzylseleno)-1,3-diphenylpropadiene, respectively, and the reaction with a mixture of dimethyl diselenide and benzylselenocyanate gave 1-benzylseleno-3-methylseleno-1,3-diphenylpropadiene together with

  由1,3-二苯丙炔和正丁基锂制备的Ph（2）C（3）二价阴离子与二甲基二硒化物和苄基硒氰酸酯的反应生成1,3-双（甲基硒基）-1,3-二苯基丙二烯和1,3-双分别与（苄基硒基）-1，3-二苯基丙二烯和与二硒基二甲基硒化物和苄基硒基氰酸酯的混合物反应，得到1-苄基硒基-3-甲基硒基-1，3-二苯基丙二烯以及对称产物。1,3-双（烷基硒基）烯丙烯的热反应可得到（E）-和（Z）-1,3,4,6-四苯基-3-己烯-1,5-二炔以及衍生自环戊二烯的化合物通过自由基途径的二烯或二烯化物。
• Reaction of 1,3-Bis(alkylseleno)allenes with Diphenyl Diazomethane
  作者：Toshio Shimizu、Daisuke Miyasaka、Nobumasa Kamigata

  DOI：10.1021/jo010287y

  日期：2001.10.1
• Convenient synthesis of aryl substituted 3-hexene-1,5-diynes
  作者：Kakuzo Isagawa、Kazuhiko Mizuno、Tetsuro Majima

  DOI：10.1016/s0040-4039(99)01745-1

  日期：1999.12

  Dimerization of alkynyl carbenes generated from the reaction of 1,1-dibromo-2,3-diarylcyclopropanes (aryl=phenyl, 4-methylphenyl, 4-chlorophenyl) with a strong base under phase-transfer conditions occurs to give E- and Z-1,3,4,6-tetraaryl-3-hexene-1,5-diynes with 1:1 ratio in high yields at ambient temperature. On the other hand, the similar reaction of 1,1-dibromo-2,3-di-(4-methoxy)phenylcyclopropane gave 4,4'-dimethoxychalcone. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Alkynylzirconation of Alkynes and Application to One-Pot Bisalkynylation of Alkynes
  作者：Yuanhong Liu、Zhenqi Zhong、Kiyohiko Nakajima、Tamotsu Takahashi

  DOI：10.1021/jo026037e

  日期：2002.10.1

  Stereocontrolled alkynylzirconation of unactivated alkynes was achieved by the reaction of an alkyne with Cp2ZrEt2 and alkynyl halide in this order. After hydrolysis of the alkynylzirconation product, trisubstituted enyne derivatives were obtained in good yields. Functionalized enynes were also prepared by the reaction of the alkynylzirconation products with a variety of electrophiles. Subsequent addition of the second alkynyl halide to the alkynylzirconation products provided an in situ protocol for bisalkynylation of alkynes into (Z)-enediynes in good yields.