3-bromomethyl-4-phenyl-1,2-butadiene | 2219-55-8

• 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: 3-bromomethyl-4-phenyl-1,2-butadiene
• 英文别名: 2-Benzyl-1-brom-buta-2,3-dien；3-Brommethyl-4-phenyl-buta-1,2-dien；1-Brom-2-benzyl-butadien-(2.3)；3-Benzyl-4-brom-buta-1,2-dien
• CAS: 2219-55-8
• 化学式: C₁₁H₁₁Br
• 分子量: 223.112
• InChiKey: VNNKLQZKJTYZJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  274.6±20.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  3
• 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：

  3-bromomethyl-4-phenyl-1,2-butadiene 在 四(三苯基膦)钯 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 cis-2-(2'-benzyl-3'-(4''-methoxyphenyl)but-2'-enyl)malononitrile
  参考文献：
  名称：

  在AcOH的存在下，钯催化向丙二烯中高度区域和立体选择性地添加有机硼酸。

  摘要：

  Pd（0）催化的有机硼酸向烯基的区域和立体选择性加成反应生成立体定义的三或四取代烯烃。此外，该方法显示出高的替代物装载能力和各种替代物的耐受性。提出了氢沉钯-铃木偶联机理，其可以解释区域选择性和立体选择性。

  DOI：

  10.1002/chem.200305301
• 作为产物：
  描述：

  2-benzylbuta-2,3-dien-1-ol 在 吡啶 、 三溴化磷 作用下， 以75%的产率得到3-bromomethyl-4-phenyl-1,2-butadiene
  参考文献：
  名称：

  Studies on Pd(II)-Catalyzed Coupling−Cyclization of α- or β-Amino Allenes with Allylic Halides

  摘要：

  The palladium-catalyzed coupling-cyclization of alpha- or beta-amino allenes with allylic halides leading to 3-allylic 2,5-dihydropyrroles and 1,2,3,6-tetrahydropyridines, respectively, was studied. The starting materials are easily available. The skeletons of both two classes of products were established by the X-ray diffraction studies of 7i and 9b. Through the study of the reaction of 2b with 3-chloro-1-butene, 1-chloro-2-butene, and pi-allyl palladium species and the stereochemical outcome of the coupling cyclization of (S)-2m and (R)-2n, it is believed that the current transformation most likely proceeded via a Pd(II)-catalyzed pathway, although a Pd(0) pathway cannot be completely excluded.

  DOI：

  10.1021/jo0342469

文献信息

• Lumbroso-Bader,N. et al., Bulletin de la Societe Chimique de France, 1967, p. 189 - 195
  作者：Lumbroso-Bader,N. et al.

  DOI：——

  日期：——
• Michel,E.; Troyanowsky,C., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1964, vol. 258, p. 3048 - 3050
  作者：Michel,E.、Troyanowsky,C.

  DOI：——

  日期：——
• Studies on Pd(II)-Catalyzed Coupling−Cyclization of α- or β-Amino Allenes with Allylic Halides
  作者：Shengming Ma、Fei Yu、Wenzhong Gao

  DOI：10.1021/jo0342469

  日期：2003.7.1

  The palladium-catalyzed coupling-cyclization of alpha- or beta-amino allenes with allylic halides leading to 3-allylic 2,5-dihydropyrroles and 1,2,3,6-tetrahydropyridines, respectively, was studied. The starting materials are easily available. The skeletons of both two classes of products were established by the X-ray diffraction studies of 7i and 9b. Through the study of the reaction of 2b with 3-chloro-1-butene, 1-chloro-2-butene, and pi-allyl palladium species and the stereochemical outcome of the coupling cyclization of (S)-2m and (R)-2n, it is believed that the current transformation most likely proceeded via a Pd(II)-catalyzed pathway, although a Pd(0) pathway cannot be completely excluded.
• Palladium-Catalyzed Highly Regio- and Stereoselective Addition of Organoboronic Acids to Allenes in the Presence of AcOH
  作者：Shengming Ma、Ning Jiao、Longwu Ye

  DOI：10.1002/chem.200305301

  日期：2003.12.15

  The Pd(0)-catalyzed regio- and stereoselective addition of organoboronic acids to allenes leads to stereodefined tri- or tetrasubstituted alkenes. Furthermore, this method shows high substitutent-loading capability and tolerance of various substitutents. A hydropalladation-Suzuki coupling mechanism, which may account for the regio- and stereoselectivity, is proposed.

  Pd（0）催化的有机硼酸向烯基的区域和立体选择性加成反应生成立体定义的三或四取代烯烃。此外，该方法显示出高的替代物装载能力和各种替代物的耐受性。提出了氢沉钯-铃木偶联机理，其可以解释区域选择性和立体选择性。