1-(buta-1,2-dien-1-yl)-4-methylbenzene | 26653-38-3

• 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: 1-(buta-1,2-dien-1-yl)-4-methylbenzene
• 英文别名: 1-(1,2-Butadienyl)-4-methylbenzene
• CAS: 26653-38-3
• 化学式: C₁₁H₁₂
• 分子量: 144.216
• InChiKey: PJSRLOZKBUNWCX-UHFFFAOYSA-N

物化性质

• 沸点：
  237.4±10.0 °C(Predicted)
• 密度：
  0.891±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  三甲基硅烷 、 1-(buta-1,2-dien-1-yl)-4-methylbenzene 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以60%的产率得到(E)-2-(trimethylsilyl)-1-(4-methylphenyl)-2-butene
  参考文献：
  名称：

  Lewis Acid Catalyzed Highly Regio- and Stereocontrolled Trans-Hydrosilylation of Alkynes and Allenes

  摘要：

  Lewis acids such as AlCl3 or EtAlCl2 dramatically catalyzed the hydrosilylation of alkynes 1 with trialkylsilanes to produce the corresponding cis-vinylsilanes 2 in a regio- and trans-stereoselective manner. For example, the hydrosilylation of 1-dodecyne la with triethylsilane in the presence of 0.2 equiv of AlCl3 gave cis-1-(triethylsilyl)-1-dodecene in 93% yield. Other alkyl- and phenyl-substituted terminal and internal acetylenes also underwent trans-hydrosilylation very smoothly. In the case of alkoxy- or silyloxy-substituted acetylenes, the use of 1.2 equiv of AlCl3 or EtAlCl2 was essential to obtain the corresponding trans-hydrosilylation products in high yields. Moreover, AlCl3 catalyzed the hydrosilylation of aromatic allenes 11, producing the alkenylsilanes 12 with high regio- and stereoselectivities in moderate to high chemical yields. Not only the simple monosubstituted, but also the disubstituted and trisubstituted allenes, underwent the hydrosilylation reaction smoothly, serving as a useful tool for the synthesis of differently substituted vinylsilanes which are not easily available through the previously known methodologies. The mechanisms for these catalytic reactions of alkynes and allenes are proposed.

  DOI：

  10.1021/jo9824293
• 作为产物：
  描述：

  4-(p-tolyl)but-3-yn-2-ol 在 2-硝基苯磺酰肼 作用下， 以60%的产率得到1-(buta-1,2-dien-1-yl)-4-methylbenzene
  参考文献：
  名称：

  金（I）催化的阿伦烯的立体会聚、分子间对映选择性加氢胺化

  摘要：

  金和银：[{( S )- 1 }(AuCl) 2 ] 和 AgBF 4的 1:2 混合物催化手性、外消旋 1,3-二取代丙二烯与 N-未取代氨基甲酸酯的对映选择性加氢胺化反应形成N-烯丙基氨基甲酸酯产率高，区域选择性和非对映选择性高，ee高达 92% （参见方案，Cbz=苄氧羰基）。

  DOI：

  10.1002/anie.201201584

文献信息

• Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes
  作者：Dimitri A. Khrakovsky、Chuanzhou Tao、Miles W. Johnson、Richard T. Thornbury、Sophia L. Shevick、F. Dean Toste

  DOI：10.1002/anie.201601550

  日期：2016.5.10

  The gold‐catalyzed enantioselective hydroazidation and hydroamination reactions of allenes are presented herein. ADC gold(I) catalysts derived from BINAM were critical for achieving high levels of enantioselectivity in both transformations. The sense of enantioinduction is reversed for the two different nucleophiles, allowing access to both enantiomers of the corresponding allylic amines using the

  本文介绍了金催化的丙二烯的对映选择性氢化叠氮化和氢胺化反应。源自 BINAM 的 ADC 金 (I) 催化剂对于在两种转化中实现高水平的对映选择性至关重要。对于两种不同的亲核试剂，对映诱导的意义是相反的，允许使用相同的催化剂对映体获得相应烯丙胺的两种对映体。
• Ruthenium-catalyzed coupling of unactivated olefins with unactivated alkynes
  作者：Masahiro Murakami、Minoru Ubukata、Yoshihiko Ito

  DOI：10.1016/s0040-4039(98)01580-9

  日期：1998.10

  A new ruthenium-catalyzed coupling reaction of an olefin with an alkyne is presented. The CH bond of the olefin formally undergoes trans addition to the CC triple bond to produce conjugated dienes.

  提出了一种新的钌催化的烯烃与炔烃的偶联反应。烯烃的CH键正式进行反除了CC三键，以产生共轭二烯。
• Carbenoid reactions by means of diethylcadmium and gem-diiodoalkane
  作者：J. Furukawa、N. Kawabata、T. Fujita

  DOI：10.1016/0040-4020(70)85024-4

  日期：——

  corresponding reaction with diethylzinc. Phenylsubstituted cyclopropane was obtained from the reaction of olefin with diethylcadmium and benzal iodide. The reaction was found to favour the syn isomer but less than the corresponding reaction with diethylzinc. Phenylpropadienes were obtained from phenylacetylenes, diethylcadmium and gem-diiodoalkane. On the other hand, in the corresponding reaction with diethylzinc

  由二乙基镉和宝石-二碘代烷制备镉类化合物，并对其反应进行了研究。烯烃与二乙基镉和亚甲基碘的反应通过立体有择的顺式加成以良好的收率得到环丙烷。烯烃，二乙基镉和亚乙基碘化物提供了Me取代的环丙烷，与相应的与二乙基锌反应的情况相反，其中的主要是抗异构体。由烯烃与二乙基镉和碘化苯的反应获得苯基取代的环丙烷。发现该反应有利于顺式异构体，但小于与二乙基锌的相应反应。苯丙二烯得自苯乙炔，二乙基镉和宝石-二碘代烷。另一方面，在与二乙基锌的相应反应中，炔属化合物的金属化作用比丙二烯的形成更为重要。
• Gold(I)-Catalyzed Stereoconvergent, Intermolecular Enantioselective Hydroamination of Allenes
  作者：Kristina L. Butler、Michele Tragni、Ross A. Widenhoefer

  DOI：10.1002/anie.201201584

  日期：2012.5.21

  Gold and silver: A 1:2 mixture of [(S)‐1}(AuCl)2] and AgBF4 catalyzes the enantioselective hydroamination of chiral, racemic 1,3‐disubstituted allenes with N‐unsubstituted carbamates to form N‐allylic carbamates in good yield, with high regio‐ and diastereoselectivity, and up to 92 % ee (see scheme, Cbz=benzyloxycarbonyl).

  金和银：[( S )- 1 }(AuCl) 2 ] 和 AgBF 4的 1:2 混合物催化手性、外消旋 1,3-二取代丙二烯与 N-未取代氨基甲酸酯的对映选择性加氢胺化反应形成N-烯丙基氨基甲酸酯产率高，区域选择性和非对映选择性高，ee高达 92% （参见方案，Cbz=苄氧羰基）。
• Palladium-catalyzed synthesis of allenes.
  作者：Tuyêt Jeffery-Luong、Gérard Linstrumelle

  DOI：10.1016/s0040-4039(00)71120-8

  日期：1980.1

  Substituted allenes are selectively obtained in good yields from the reaction of Grignard reagents with propargylic or allenic halides in the presence of catalytic amounts of palladium chloride, triphenylphosphine and diisobutyl aluminum hydride, in tetrahydrofuran at room temperature.

  在室温下，在四氢呋喃中，在催化量的氯化钯，三苯膦和氢化二异丁基铝存在下，从格氏试剂与炔丙基或烯丙基卤的反应选择性地以高收率选择性地获得取代的烯。