3,4-bis(methylene)-2,5-diphenyl-1,5-hexadiene

• 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: 3,4-bis(methylene)-2,5-diphenyl-1,5-hexadiene
• 英文别名: (3,4-Dimethylidene-5-phenylhexa-1,5-dien-2-yl)benzene
• 化学式: C₂₀H₁₈
• 分子量: 258.363
• InChiKey: HYHIEVAJUWXHBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-iodo-3-phenyl-1,3-butadiene 在 四(三苯基膦)钯 、 甲基锂 作用下， 以 苯 为溶剂， 以63%的产率得到3,4-bis(methylene)-2,5-diphenyl-1,5-hexadiene
  参考文献：
  名称：

  Preparation of 2-Iodo-1,3-butadienes from 1-Trimethylsilyl-2,3-butadienes and their Functionalizations

  摘要：

  Successive treatment of 1-trimethylsilyl-2,3-butadienes with iodine and tetra-n-butylammonium fluoride in the same flask affords 2-iodo-1,3-butadienes in good yields and their palladium-catalyzed carbonylation and alkynylation allows introduction of ester and alkynyl groups to the 2-position bearing an iodine atom leading to various 2,3-disubstituted 1,3-butadienes. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10413-0

文献信息

• Facile Synthesis of Dendralenes Based on the Cross-coupling Reaction of 2,3-Bis(pinacolato)boryl-1,3-butadiene
  作者：Masaki Shimizu、Kei Tanaka、Takuya Kurahashi、Katsuhiro Shimono、Tamejiro Hiyama

  DOI：10.1246/cl.2004.1066

  日期：2004.8

  Palladium-catalyzed cross-coupling reaction of 2,3-diboryl1,3-butadiene with an alkenyl halide or a dienyl halide allowed us to straightforwardly prepare various kinds of acyclic cross-conjugated polyenes that are referred to as dendralenes. The present method is applicable to the synthesis of not only symmetrical [4]- and [6]dendralenes but also unsymmetrical [3]-to [5]dendralenes.

  钯催化的 2,3-二硼基 1,3-丁二烯与链烯基卤化物或二烯基卤化物的交叉偶联反应使我们能够直接制备各种无环交叉共轭多烯，即树枝状烯。本方法不仅适用于对称[4]-和[6]树枝烯的合成，也适用于不对称[3]-至[5]树枝烯的合成。
• From propargylic biscarbonate to diaryl[n]dendralenes
  作者：Shotaro Hayashi、Masakatsu Kasuya、Junsuke Machida、Toshio Koizumi

  DOI：10.1016/j.tetlet.2017.05.016

  日期：2017.6

  An efficient cross-coupling reaction using a low cost carbon-supported palladium (Pd/C) catalyst for the synthesis of cross-conjugated compounds, diaryl[n]dendralenes, has been developed. The reaction of a propargylic biscarbonate with phenylboronic acid using Pd/C and phosphine ligand (S-Phos) gave 2,3-diphenyl[2]dendralene in high yield. We found that Pd/C was an effective catalyst for the synthesis of dialyl[n]dendralenes. The synthesis of various dendralenes was successfully achieved under the optimized conditions, giving dialyl [2] and [4] dendralenes in good yields. (C) 2017 Elsevier Ltd. All rights reserved.