(E)-1,4-Diphenyl-3-penten-1-yne | 142025-12-5

• 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: (E)-1,4-Diphenyl-3-penten-1-yne
• 英文别名: (E)-1-methyl-1,4-diphenyl-1-buten-3-yne；(E)-pent-3-en-1-yne-1,4-diyldibenzene；(E)-1-methyl-1-phenyl-4-phenyl-but-1-en-3-yne；[(E)-4-phenylpent-3-en-1-ynyl]benzene
• CAS: 142025-12-5
• 化学式: C₁₇H₁₄
• 分子量: 218.298
• InChiKey: BCXFLUZVVUUJME-OQLLNIDSSA-N

物化性质

• 熔点：
  100-102 °C
• 沸点：
  339.9±25.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (E)-1,4-Diphenyl-3-penten-1-yne 在 Cu(bphen)(XantPhos)BF₄ 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以97%的产率得到(Z)-1-methyl-1,4-diphenylbut-1-en-3-yne
  参考文献：
  名称：

  用于能量转移过程的杂配铜基配合物：E → Z异构化和串联光催化序列

  摘要：

  涉及铜配合物的能量转移过程很少见。使用优化的杂配铜配合物 Cu( bphen )( XantPhos )BF 4，证明了烯烃的光敏E → Z异构化。所述XANTPHOS配体，得到具有改善的催化剂稳定性的增感剂，同时将BPhen配体延长了激发态寿命。一系列 25 个二取代和三取代烯烃经历了光异构化，包括大环和 1,3-烯炔。Cu( bphen )( XantPhos )BF 4 也可以在使用芳基磺酰氯的串联 ATRA/光异构化过程中使用，这是使用卤化物取代的烯烃进行光异构化的一个例子。

  DOI：

  10.1021/acscatal.1c01983
• 作为产物：
  描述：

  2-苯基丙醛 在 palladium(II) trifluoroacetate 、 sodium acetate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 (E)-1,4-Diphenyl-3-penten-1-yne
  参考文献：
  名称：

  使用牺牲导向基团从 β-硝基烯烃立体选择性合成 (E)-1,3-烯炔的 Pd 催化串联途径

  摘要：

  跳舞杂交：描述了仅从烯烃底物有效且立体选择性 ( E )-1,3-烯炔合成的第一个例子。硝基作为牺牲导向基团的诞生，通过促进零级到三级升级形成神奇的三键，使该方法原子和步骤高效且可持续。

  DOI：

  10.1002/chem.202301637

文献信息

• Synthesis of (E)-1,4-bis(organyl) but-1-en-3-ynes by lithlium-tellurium exchange reaction on (Z)-1-butyltelluro-1,4-bis(organyl) but-1-en-3-ynes.
  作者：Miguel J. Dabdoub、Vânia B. Dabdoub、João V. Comasseto

  DOI：10.1016/s0040-4039(00)74184-0

  日期：1992.4

  react with dibutyl ditelluride and sodium borohydride in ethanol under reflux to give (Z)-1-butyltelluro-1,4-bis(organyl) but-1-en-3-ynes, which by treatment with butyllithium followed by water give (E)-1,4-bis(organyl) but-1-en-3-ynes in high yields.

  1,4-双）有机基）-1,3-丁二炔与二丁基二碲化物和硼氢化钠在乙醇中在回流下反应生成（Z）-1-丁基碲-1,4-双（有机基）but-1-en-3 -ynes，先用丁基锂然后用水处理，以高收率得到（E）-1,4-双（有机基）but-1-en-3-ynes。
• Synthesis of aryl- and vinylacetylene derivatives by copper-catalyzed reaction of aryl and vinyl iodides with terminal alkynes
  作者：Kazumi Okuro、Makoto Furuune、Masahiro Enna、Masahiro Miura、Masakatsu Nomura

  DOI：10.1021/jo00069a040

  日期：1993.8

  The coupling reaction of aryl iodides with terminal alkynes by using a catalyst system of CuI-PPhs in the presence of K2CO3 as base gives the corresponding arylated alkynes in excellent yields. Addition of PPh3 is essential for the reaction to proceed catalytically. Vinyl iodides also react smoothly with the alkynes to give enyne compounds with retention of the configurations. While DMF and DMSO can be used as solvents, DMSO is found to be effective for the reaction with aliphatic terminal alkynes. A reaction mechanism involving initial formation of copper acetylide species coordinated by PPh3 followed by reaction of aryl and vinyl iodides is proposed.
• Highly regio- and stereoselective synthesis of 1,3-enynes from unactivated ethylenes via palladium-catalyzed cross-coupling
  作者：Yanmei Wen、Azhong Wang、Huanfeng Jiang、Shifa Zhu、Liangbin Huang

  DOI：10.1016/j.tetlet.2011.07.092

  日期：2011.11

  An efficient procedure for regio- and stereoselective synthesis of a series of conjugated enynes by a simple Pd-catalyzed cross-coupling reaction of unactivated ethylenes and ethynyl bromide has been developed. The reaction proceeds smoothly in DMF to give the corresponding products in good to excellent yields. The protocol can tolerate a broad range of functional groups on the substrates. (C) 2011 Elsevier Ltd. All rights reserved.
• Highly Regio- and Stereoselective Synthesis of Boron-Substituted Enynes via Copper-Catalyzed Borylation of Conjugated Diynes
  作者：DingXi Li、Yeong Eun Kim、Jaesook Yun

  DOI：10.1021/ol503720w

  日期：2015.2.20

  A mild copper-catalyzed regio- and stereoselective monoborylation of conjugated diynes with bis(pinacolato)diboron that affords enynylboronates is reported. The reaction is efficient for different types of conjugated diynes including unsymmetrical diynes and produces enynylboron compounds with high and complementary regioselectivity compared with classical hydrometalation reactions. In particular, the reactions of internal conjugated diynes with a silyl substitution produced highly functionalized enynes with high regio- and stereoselectivity, which can be used in further transformations.