2-iodo-1,1-diphenylpropene | 81360-97-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-iodo-1,1-diphenylpropene
• 英文别名: (2-iodo-1-phenylprop-1-enyl)benzene
• CAS: 81360-97-6
• 化学式: C₁₅H₁₃I
• 分子量: 320.173
• InChiKey: BFEWOKLXUIPMEE-UHFFFAOYSA-N

物化性质

• 沸点：
  348.8±31.0 °C(Predicted)
• 密度：
  1.485±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  2-iodo-1,1-diphenylpropene 以44%的产率得到
  参考文献：
  名称：

  KITAMURA, TSUGIO;KOBAYASHI, SHINJIRO;TANIGUCHI, HIROSHI, J. ORG. CHEM., 1982, 47, N 12, 2323-2328

  摘要：

  DOI：
• 作为产物：
  描述：

  1,1-diphenylprop-1-en-2-yl trifluoromethanesulfonate 在 三乙胺 、 magnesium iodide 作用下， 以 环己烷 为溶剂， 反应 10.0h， 以83%的产率得到2-iodo-1,1-diphenylpropene
  参考文献：
  名称：

  Palladium-Catalyzed Annulation of Internal Alkynes by Arene-Containing Vinylic Iodides and Triflates

  摘要：

  In the presence of a palladium catalyst, internal alkynes undergo carboannulation by cyclic and acyclic vinylic iodides and triflates bearing a neighboring aromatic ring to produce a variety of carbocycles. For example, a number of 9,10-disubstituted-1,2,3,4-tetrahydrophenanthrenes have been prepared in good yields through the palladium-catalyzed annulation of internal alkynes by 2-phenyl-1-cyclohexenyl triflate (1) or 1-iodo-2-phenylcyclohexene (2). This annulation process is fairly general and highly regioselective. The process appears to involve oxidative addition of the vinylic substrate to Pd(0) to produce a vinylic palladium intermediate, which adds the carbon moiety to the less hindered end and the palladium to the more hindered end of the alkyne, followed by intramolecular ring closure onto the neighboring aryl group. The scope and limitations of this methodology are discussed.

  DOI：

  10.1021/jo972154b

文献信息

• Highly Efficient Route to Fused Polycyclic Aromatics via Palladium-Catalyzed Aryne Annulation by Aryl Halides
  作者：Zhijian Liu、Richard C. Larock

  DOI：10.1021/jo0619534

  日期：2007.1.1

  Polycyclic aromatic and heteroaromatic hydrocarbons have been synthesized in high yield by two different processes involving the Pd-catalyzed annulation of arynes. The first process involves a Pd-catalyzed annulation of arynes by 2-halobiaryls and related vinylic halides. The second process utilizes a Pd-catalyzed double annulation of arynes by simple aryl halides. Both processes appear to involve

  多环芳族和杂芳族烃已通过涉及钯催化的芳烃环化的两种不同方法以高收率合成。第一个过程涉及2-卤代联芳基和相关的乙烯基卤化物的钯催化芳烃的环化反应。第二种方法是通过简单的芳基卤化物利用Pd催化的芳烃双环。两种方法似乎都涉及两个反应性很强的底物，芳烃和有机钯物质的催化，逐步偶联，以产生优异的交叉偶联产物收率。
• Synthesis of Multisubstituted Triphenylenes and Phenanthrenes by Cascade Reaction of <i>o</i>-Iodobiphenyls or (<i>Z</i>)-β-Halostyrenes with <i>o</i>-Bromobenzyl Alcohols through Two Sequential C–C Bond Formations Catalyzed by a Palladium Complex
  作者：Masayuki Iwasaki、Yasuhiro Araki、Shohei Iino、Yasushi Nishihara

  DOI：10.1021/acs.joc.5b01693

  日期：2015.9.18

  bearing both nucleophilic and electrophilic substituents, for the facile synthesis of polycyclic aromatic hydrocarbons. A palladium/electron-deficient phosphine catalyst efficiently coupled o-iodobiphenyls or (Z)-β-halostyrenes with o-bromobenzyl alcohols to afford triphenylenes and phenanthrenes, respectively. The present cascade reaction proceeded through deacetonative cross-coupling and sequential intramolecular

  邻溴苄醇已被开发为一种新型的带有亲核和亲电取代基的环化试剂，可轻松合成多环芳烃。钯/电子不足的膦催化剂有效地将邻碘联苯或（Z）-β-卤代苯乙烯与邻溴苄醇偶联，分别制得三亚苯基和菲。目前的级联反应是通过去乙酰化交叉偶联和顺序分子内环化进行的。大量实验数据表明，反应机理涉及1,4-钯迁移的平衡。
• Phenanthrene Synthesis by Palladium-Catalyzed Benzannulation with <i>o</i>-Bromobenzyl Alcohols through Multiple Carbon–Carbon Bond Formations
  作者：Masayuki Iwasaki、Yasuhiro Araki、Yasushi Nishihara

  DOI：10.1021/acs.joc.7b00848

  日期：2017.6.16

  benzannulation with o-bromobenzyl alcohols enabled the facile construction of phenanthrene skeletons via the sequential multiple carbon–carbon bond formations. A variety of multisubstituted phenanthrenes were synthesized by the reaction of (Z)-β-halostyrenes with o-bromobenzyl alcohols as well as by the three-component coupling of alkynes, aryl bromides, and o-bromobenzyl alcohols. The electron-deficient phosphine

  邻溴苄醇与钯催化的苯环合可以通过连续的多个碳-碳键形成而轻松地构建菲骨架。多种多取代菲的通过的（反应合成Ž）-β-卤代苯乙烯与ö -bromobenzyl醇以及由炔烃组成的三组分偶联，芳基溴化物和ö-溴苄醇。缺电子的膦配体在控制所用的两种不同有机卤化物的顺序氧化加成中起着重要作用，从而实现了以良好的收率选择性形成所需的菲。该合成方案也适用于高度稠合的多环芳族烃如四苯的合成。
• Photolysis of vinyl halides. Preferential formation of vinyl cations by copper(II) salts
  作者：Tsugio. Kitamura、Shinijiro. Kobayashi、Hiroshi. Taniguchi

  DOI：10.1021/ja00270a023

  日期：1986.5

  Photolysis of vinyl halides in the presence of copper(II) salts resulted in a significant suppression of product formation derived from vinyl radicals. Photolysis of 1,1-diaryl-2-bromopropenes in the presence of copper(II) salts yielded no 1,1-diaryl-2-propenes. Photolysis of other vinyl halides, i.e., 1,1-diaryl-2-iodopropenes, 1,1-diaryl-2-bromoethylenes, and 1-bromo-2-(p-methoxyphenyl)ethylene,

  在铜 (II) 盐存在下卤乙烯的光解导致乙烯基产物形成的显着抑制。在铜 (II) 盐的存在下，1,1-二芳基-2-溴丙烯的光解没有产生 1,1-二芳基-2-丙烯。其他乙烯基卤化物，即 1,1-二芳基-2-碘丙烯、1,1-二芳基-2-溴乙烯和 1-溴-2-(对甲氧基苯基)乙烯的光解也导致衍生自乙烯基自由基的还原烯烃的产率。发现三氟甲磺酸铜 (II) 对乙烯基自由基的氧化比乙酸铜 (II) 更有效。这些反应可以通过乙烯基铜中间体的介入和乙烯基阳离子的形成来解释。
• Photochemistry of vinyl halides. Vinyl cation from photolysis of 1,1-diaryl-2-halopropenes
  作者：Tsugio Kitamura、Shinjiro Kobayashi、Hiroshi Taniguchi

  DOI：10.1021/jo00133a018

  日期：1982.6