4-methyl-3-phenylpent-3-en-1-yne | 65050-80-8

• 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: 4-methyl-3-phenylpent-3-en-1-yne
• 英文别名: Pent-1-yn-3-ene, 4-methyl-3-phenyl-；4-methylpent-3-en-1-yn-3-ylbenzene
• CAS: 65050-80-8
• 化学式: C₁₂H₁₂
• 分子量: 156.227
• InChiKey: KMTOCKMZARAVFR-UHFFFAOYSA-N

物化性质

• 沸点：
  95 °C(Press: 18 Torr)
• 密度：
  0.936±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  4-methyl-3-phenylpent-3-en-1-yne 、 重氮乙酸甲酯 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 以25%的产率得到dimethyl (1R,2R,3S,4S,5S,6S)-1,2-bis(2-methyl-1-phenylprop-1-enyl)tricyclo[3.1.0.02,4]hexane-3,6-dicarboxylate
  参考文献：
  名称：

  Regioselective Rh2(OAc)4-promoted reactions of methyl diazoacetate with terminal triple bond enynes

  摘要：

  The selective Rh-2(OAc)(4)-promoted methoxycarbonylmethylenation of a triple bond in enynes, with a terminal triple bond. by methyl diazoacetate is established, and the main factors, affecting the regioselectivity of the process, are elucidated. The easy in situ [2 + 2]-dimerization of methyl 1-alkenylcyclopropene-3-carboxylates in dimethyl trans-1,2-dialkenyltricyclo[3.1.0.0(2,4)] hexane 3,6-dicarboxylates 2 is found, and their thermal rearrangement into dimethyl trans-1.2-dialkenylcyclohexa-1 ,4-diene-3,6-dicarboxylates 7 is also described.

  DOI：

  10.1039/p29940000709
• 作为产物：
  描述：

  4-methyl-3-phenylpent-1-yn-3-ol 在 magnesium sulfate 作用下， 250.0 ℃ 、2.0 kPa 条件下， 反应 1.5h， 以57%的产率得到4-methyl-3-phenylpent-3-en-1-yne
  参考文献：
  名称：

  Regioselective Rh2(OAc)4-promoted reactions of methyl diazoacetate with terminal triple bond enynes

  摘要：

  The selective Rh-2(OAc)(4)-promoted methoxycarbonylmethylenation of a triple bond in enynes, with a terminal triple bond. by methyl diazoacetate is established, and the main factors, affecting the regioselectivity of the process, are elucidated. The easy in situ [2 + 2]-dimerization of methyl 1-alkenylcyclopropene-3-carboxylates in dimethyl trans-1,2-dialkenyltricyclo[3.1.0.0(2,4)] hexane 3,6-dicarboxylates 2 is found, and their thermal rearrangement into dimethyl trans-1.2-dialkenylcyclohexa-1 ,4-diene-3,6-dicarboxylates 7 is also described.

  DOI：

  10.1039/p29940000709

文献信息

• Iron-Catalyzed Vinylzincation of Terminal Alkynes
  作者：Qiang Huang、Yu-Xuan Su、Wei Sun、Meng-Yang Hu、Wei-Na Wang、Shou-Fei Zhu

  DOI：10.1021/jacs.1c11072

  日期：2022.1.12

  Organozinc reagents are among the most commonly used organometallic reagents in modern synthetic chemistry, and multifunctionalized organozinc reagents can be synthesized from structurally simple, readily available ones by means of alkyne carbozincation. However, this method suffers from poor tolerance for terminal alkynes, and transformation of the newly introduced organic groups is difficult, which

  有机锌试剂是现代合成化学中最常用的有机金属试剂之一，多官能化的有机锌试剂可以通过炔烃碳酰化从结构简单、容易获得的有机锌试剂中合成。但该方法对末端炔烃的耐受性较差，且新引入的有机基团难以转化，限制了其应用。在此，我们报告了一种由新开发的带有 1,10-菲咯啉-亚胺配体的铁催化剂催化的末端炔烃的乙烯基锌化方法。该方法提供了从现成的乙烯基锌试剂和末端炔烃中有效获取具有多种结构和官能团的新型有机锌试剂的途径。该方法具有优异的官能团耐受性（可耐受的官能团包括氨基、酰胺、氰基、酯、羟基、磺酰基、缩醛、膦酰基、吡啶基），良好的底物范围（合适的末端炔烃包括具有各种官能团的芳基、烯基和烷基乙炔）组），以及高化学选择性、区域选择性和立体选择性。该方法可以显着提高包括维生素A在内的各种重要生物活性分子的合成效率。机理研究表明，本研究开发的新型铁-1,10-菲咯啉-亚胺催化剂具有极其拥挤的反应袋，促进了化合物的高
• Stereospecific formation of conjugated dienes from 3-alken-1-ynes and organocuprates. Application in the systhesis of myrcene.
  作者：Hans Westmijze、Henk Kleijn、John Meijer、Peter Vermeer

  DOI：10.1016/s0040-4039(01)92778-9

  日期：1977.1
• Kleijn,H. et al., Recueil des Travaux Chimiques des Pays-Bas, 1977, vol. 96, p. 251 - 254
  作者：Kleijn,H. et al.

  DOI：——

  日期：——
• KLEIJN H.; MEIJER J.; WESTMIJZE H.; VERMEER P., REC. TRAV. CHIM., 1977, 96, NO 10, 251-254
  作者：KLEIJN H.、 MEIJER J.、 WESTMIJZE H.、 VERMEER P.

  DOI：——

  日期：——
• Regioselective Rh2(OAc)4-promoted reactions of methyl diazoacetate with terminal triple bond enynes
  作者：Evgeny A. Shapiro、Alexey V. Kalinin、Bogdan I. Ugrak、Oleg M. Nefedov

  DOI：10.1039/p29940000709

  日期：——

  The selective Rh-2(OAc)(4)-promoted methoxycarbonylmethylenation of a triple bond in enynes, with a terminal triple bond. by methyl diazoacetate is established, and the main factors, affecting the regioselectivity of the process, are elucidated. The easy in situ [2 + 2]-dimerization of methyl 1-alkenylcyclopropene-3-carboxylates in dimethyl trans-1,2-dialkenyltricyclo[3.1.0.0(2,4)] hexane 3,6-dicarboxylates 2 is found, and their thermal rearrangement into dimethyl trans-1.2-dialkenylcyclohexa-1 ,4-diene-3,6-dicarboxylates 7 is also described.