(5-methylhexa-1,2-dienyl)benzene | 27694-91-3

• 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: (5-methylhexa-1,2-dienyl)benzene
• 英文别名: (5-Methyl-1,2-hexadienyl)benzene
• CAS: 27694-91-3
• 化学式: C₁₃H₁₆
• 分子量: 172.27
• InChiKey: KDGPRRICWFMXLR-UHFFFAOYSA-N

物化性质

• 沸点：
  84-85 °C(Press: 4 Torr)
• 密度：
  0.8931 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (5-methylhexa-1,2-dienyl)benzene 、 7-methylbicyclo[4.2.0]octa-1,3,5-trien-7-ol 在 [Rh(OH)(cod)]2 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以81.818%的产率得到
  参考文献：
  名称：

  Rh（I）催化的丙二烯插入苯并环丁烯醇的C–C键

  摘要：

  在本文中，我们报告了通过使用对称和不对称的丙二烯，Rh（I）催化两个碳插入到苯并环丁烯醇的C–C键中。该反应提供了以良好的收率和非对映选择性快速接近带有两个相邻立体异构中心的亚烷基四氢化萘。

  DOI：

  10.1021/acs.orglett.5b03518
• 作为产物：
  描述：

  苯乙炔 在 正丁基锂 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 11.33h， 生成 (5-methylhexa-1,2-dienyl)benzene
  参考文献：
  名称：

  SAMDI Mass Spectrometry-Enabled High-Throughput Optimization of a Traceless Petasis Reaction

  摘要：

  Development of the self-assembled monolayer/MALDI mass spectrometry (SAMDI) platform to enable a high-throughput optimization of a traceless Petasis reaction is described. More than 1800 unique reactions were conducted simultaneously on an array of self-assembled monolayers of alkanethiolates on gold to arrive at optimized conditions, which were then successfully transferred to the solution phase. The utility of this reaction was validated by the efficient synthesis of a variety of di- and trisubstituted allenes.

  DOI：

  10.1021/acscombsci.5b00131

文献信息

• Gold‐Catalyzed One‐Pot Synthesis of 1,3‐Disubstituted Allenes from Benzaldehydes and Terminal Alkynes
  作者：Danilo M. Lustosa、Simon Clemens、Matthias Rudolph、A. Stephen K. Hashmi

  DOI：10.1002/adsc.201900824

  日期：2019.11.5

  A new and facile one‐pot synthesis of 1,3‐disubstituted allenes, using cheap and readily available terminal alkynes, benzaldehyde derivatives and morpholine, was developed. A small library of 20 allenes demonstrates a broad applicability, with yields up to 86%. Isotopic‐labelling and cross‐over experiments strongly indicate that our reaction proceeds via a two‐step A3‐coupling followed by a 1,5‐hydrogen

  开发了一种新的且简便的单锅合成1,3-二取代的烯，使用廉价且容易获得的末端炔烃，苯甲醛衍生物和吗啉。一个由20个Allenes组成的小型文库证明了其广泛的适用性，收率高达86％。同位素标记和交叉实验强烈表明，我们的反应是通过两步A 3偶联然后进行1,5氢转移过程进行的。
• Preparation of allenes and acetylenes from ethynylalkanol acetates via organoboranes
  作者：M. Mark Midland

  DOI：10.1021/jo00435a034

  日期：1977.7
• SAMDI Mass Spectrometry-Enabled High-Throughput Optimization of a Traceless Petasis Reaction
  作者：Abdallah B. Diagne、Shuheng Li、Gregory A. Perkowski、Milan Mrksich、Regan J. Thomson

  DOI：10.1021/acscombsci.5b00131

  日期：2015.11.9

  Development of the self-assembled monolayer/MALDI mass spectrometry (SAMDI) platform to enable a high-throughput optimization of a traceless Petasis reaction is described. More than 1800 unique reactions were conducted simultaneously on an array of self-assembled monolayers of alkanethiolates on gold to arrive at optimized conditions, which were then successfully transferred to the solution phase. The utility of this reaction was validated by the efficient synthesis of a variety of di- and trisubstituted allenes.
• Rh(I)-Catalyzed Insertion of Allenes into C–C Bonds of Benzocyclobutenols
  作者：Chunliang Zhao、Li-Chuan Liu、Jing Wang、Chenran Jiang、Qing-Wei Zhang、Wei He

  DOI：10.1021/acs.orglett.5b03518

  日期：2016.1.15

  Herein we report a Rh(I)-catalyzed two carbon insertion into C–C bonds of benzocyclobutenols by employing symmetrical and unsymmetrical allenes. This reaction provides rapid access to alkylidene tetralins bearing two adjacent stereogenic centers in good yields and diasteroselectivities.

  在本文中，我们报告了通过使用对称和不对称的丙二烯，Rh（I）催化两个碳插入到苯并环丁烯醇的C–C键中。该反应提供了以良好的收率和非对映选择性快速接近带有两个相邻立体异构中心的亚烷基四氢化萘。