1-甲基-4-[3-(4-甲基苯基)丁-1-烯基]苯 | 61909-63-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1-甲基-4-[3-(4-甲基苯基)丁-1-烯基]苯
• 英文名称: 1,1'-(But-1-ene-1,3-diyl)bis(4-methylbenzene)
• 英文别名: 1-methyl-4-[3-(4-methylphenyl)but-1-enyl]benzene
• CAS: 61909-63-5
• 化学式: C₁₈H₂₀
• 分子量: 236.357
• InChiKey: DRIJGEJOLOPSGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  1-甲基-4-[3-(4-甲基苯基)丁-1-烯基]苯 在 potassium disulfide 、 二甲基亚砜 作用下， 反应 24.0h， 以82%的产率得到2,4-二(4-甲基苯基)噻吩
  参考文献：
  名称：

  过渡金属的无硫硫化/烯烃环化：通过多个C–H键的裂解实现对噻吩的经济利用

  摘要：

  提出了一种新颖的，原子经济的，无过渡金属的策略，用于用硫化钾从取代的丁-1-烯合成噻吩。该反应可通过裂解多个C–H键实现双C–S键形成，并提供了一种有效的方法来接近各种官能化的噻吩。此外，该策略也可用于由1,4-二芳基-1,3-二烯合成噻吩。从机理上讲，DMSO起到氧化剂的作用，并涉及由K 2 S原位产生的S 3 •。

  DOI：

  10.1021/acs.orglett.8b03078
• 作为产物：
  描述：

  Alpha-甲基苯乙烯 在 air 、 palladium diacetate 、 溶剂黄146 作用下， 20.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 以67%的产率得到1-甲基-4-[3-(4-甲基苯基)丁-1-烯基]苯
  参考文献：
  名称：

  A New Type of Carbonylation of Styrenes Catalyzed by Pd(OAc)₂Combined with Molybdovanadophosphate

  摘要：

  一种新型的苯乙烯羰基化反应在1:1的CO（0.5 atm）和O2（0.5 atm）混合气氛中进行，借助Pd(OAc)2与H5PMo10V2O40·nH2O的结合，可以以78%的产率得到4-甲基-2-苯基萘-1(4H)-酮。还对多种替代的苯乙烯进行了羰基化反应，得到相应的替代芳基萘-1(4H)-酮，且产率适中。研究发现，该反应分为两个阶段：首先是苯乙烯的头尾二聚化，随后是生成的二聚体的羰基化。在没有CO的情况下，即使在室温下，苯乙烯也能在空气（1 atm）中高效二聚，形成头尾二聚体，并且产率良好。

  DOI：

  10.1246/bcsj.80.1194

文献信息

• One-pot synthesis of 1,3-diaryl but-1-enes from 1-arylethanols over Snβ zeolite
  作者：Naresh Mameda、Krishna Sai Gajula、Swamy Peraka、Srujana Kodumuri、Durgaiah Chevella、Rammurthy Banothu、Vasu Amrutham、Narender Nama

  DOI：10.1016/j.catcom.2016.11.026

  日期：2017.2

  for the one-pot synthesis of 1,3-diaryl but-1-enes from 1-arylethanols via dehydration of 1-arylethanols followed by head-to-tail dimerization of vinylarenes over heterogeneous catalyst (Snβ zeolite). The scope of the reaction was explored for various 1-arylethanols and afforded the corresponding dimers in good to excellent yields with high regio- and stereoselectivity. Moreover, Snβ zeolite could be

  已成功开发了一种环境友好的催化方案，用于通过1-芳基乙醇的脱水反应，然后在非均相催化剂上将乙烯基芳烃从头到尾进行二聚，由1-芳基乙醇一锅法合成1,3-二芳基丁-1-烯。 Snβ沸石）。探索了各种1-芳基乙醇的反应范围，并以高至优异的产率以及高的区域和立体选择性提供了相应的二聚体。而且，Snβ沸石可以容易地回收和再利用而不会显着损失其催化活性。
• Allylic Carbon–Carbon Double Bond Directed Pd-Catalyzed Oxidative <i>ortho</i>-Olefination of Arenes
  作者：Parthasarathy Gandeepan、Chien-Hong Cheng

  DOI：10.1021/ja300168m

  日期：2012.4.4

  Pd-catalyzed selective ortho-olefination of arenes assisted by an allylic C-C double bond at room temperature using O-2 as a terminal oxidant is described. A possible mechanism involving the initial coordination of allylic C=C bond to Pd followed by selective o-C-H bond metalation is proposed.
• Chemoselective hydroamination of vinyl arenes catalyzed by an NHC-amidate-alkoxide Pd(II) complex and p-TsOH
  作者：Richard Giles、Justin O’Neill、Joo Ho Lee、Michael K. Chiu、Kyung Woon Jung

  DOI：10.1016/j.tetlet.2013.05.101

  日期：2013.7

  The hydroamination of various substituted vinyl arenes with benzenesulfonamide was explored using an NHC-amidate-alkoxide palladium catalyst in conjunction with p-TsOH. Utilizing halide-substituted and electron-rich vinyl arenes, this methodology selectively furnished the cross-coupled hydroamination products in moderate to excellent yields in a Markovnikov fashion while greatly reducing undesired acid-catalyzed homocoupling of the vinyl arenes. Electron-rich vinyl arenes typically required milder conditions than electron-poor ones. While most effective for para-substituted substrates, the catalyst system also furnished the desired products from ortho- and meta-substituted vinyl arenes with high chemoselectivities. (C) 2013 Elsevier Ltd. All rights reserved.
• R-Allyl Nickel(II) Complexes with Chelating N-Heterocyclic Carbenes: Synthesis, Structural Characterization, and Catalytic Activity
  作者：Lourdes Benı́tez Junquera、M. Carmen Puerta、Pedro Valerga

  DOI：10.1021/om200937d

  日期：2012.3.26

  The N-heterocyclic carbene (NHC) nickel complexes [(L)Ni(NHC)][BAr4F] (Ar-F = 3,5-bis(trifluoromethyl)-phenyl; L = allyl (1), methylallyl (2); NHC = 1-(2-picolyl)-3-methylimidazol-2-ylidene (a), 1-(2-picolyl)-3-isopropylimidazol-2-ylidene (b), 1-(2-picolyl)-3-n-butylimidazol-2-ylidene (c), 1-(2-picolyl)-3-phenylimidazol-2-ylidene (d), 1-(2-picolyl)-3-methylbenzoimidazol-2-ylidene (e), 1-(2-picolyl)-4,5-dichloro-3-methylimidazol-2-ylidene (0) have been obtained in high yields and characterized by NMR spectroscopy. Furthermore, Id was unambiguously characterized by single-crystal X-ray crystallography. Complexes 1a-f/2a-f have shown catalytic activity toward dimerization and hydrosilylation of styrenes. In particular, 1a proved to be the most efficient catalyst in the dimerization of styrene derivatives in the absence of cocatalyst. Also, complexes 1a,d showed high selectivity and moderate to good yields in hydrosilylation reactions.
• A New Type of Carbonylation of Styrenes Catalyzed by Pd(OAc)₂Combined with Molybdovanadophosphate
  作者：Shingo Yamada、Yasushi Obora、Satoshi Sakaguchi、Yasutaka Ishii

  DOI：10.1246/bcsj.80.1194

  日期：2007.6.15

  A new type of carbonylation of styrenes was achieved under a 1:1 mixture of CO (0.5 atm) and O2 (0.5 atm) in the presence of Pd(OAc)2 combined with H5PMo10V2O40·nH2O to give 4-methyl-2-phenylnaphthalen-1(4H)-one in 78% yield. Various substituted styrenes were also carbonylated to the corresponding substituted arylnaphthalen-1(4H)-ones in moderate yields. The reaction was found to proceed in two stages involving the head-to-tail dimerization of styrenes, followed by carbonylation of the resulting dimers. Styrenes were efficiently dimerized under air (1 atm) in the absence of CO even at room temperature to produce head-to-tail dimers in good yields.

  一种新型的苯乙烯羰基化反应在1:1的CO（0.5 atm）和O2（0.5 atm）混合气氛中进行，借助Pd(OAc)2与H5PMo10V2O40·nH2O的结合，可以以78%的产率得到4-甲基-2-苯基萘-1(4H)-酮。还对多种替代的苯乙烯进行了羰基化反应，得到相应的替代芳基萘-1(4H)-酮，且产率适中。研究发现，该反应分为两个阶段：首先是苯乙烯的头尾二聚化，随后是生成的二聚体的羰基化。在没有CO的情况下，即使在室温下，苯乙烯也能在空气（1 atm）中高效二聚，形成头尾二聚体，并且产率良好。