1,5-二苯基-1,4-戊二烯 | 26057-47-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,5-二苯基-1,4-戊二烯
• 英文名称: (1E,4Z)-1,5-diphenyl-1,4-pentadiene
• 英文别名: (1Z,4E)-1,5-diphenylpenta-1,4-diene；(Z,E)-1,5-Diphenyl-penta-1,4-dien；[(1Z,4E)-5-phenylpenta-1,4-dienyl]benzene
• CAS: 26057-47-6；26057-48-7；52267-15-9；26057-49-8
• 化学式: C₁₇H₁₆
• 分子量: 220.314
• InChiKey: UORWAUAKEOUUND-DJJIWSAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902909090

反应信息

• 作为产物：
  描述：

  (Z)-β-bromostyrene 在 copper(l) iodide 作用下， 以 乙醚 为溶剂， 生成 1,5-二苯基-1,4-戊二烯
  参考文献：
  名称：

  Alkylation of allylic derivatives. 17. Cross-coupling reactions of diallylic pivalates with butyl- and phenylcopper reagents

  摘要：

  Cross coupling (Z)-1-phenyl-1,4-pentadien-3-yl pivalate (cis-1-OPiv) with LiCuBu2, LiCu(CN)Bu, LiCuPh2, and LiCu(CN)Ph gives only the fully conjugated gamma-coupling product. With LiCuBu2, substantial loss of double-bond configuration occurs to give primarily the all-trans coupling product. With other cuprates, no detectable loss of double-bond configuration was observed. Cross coupling (Z)-3-(2-phenylethenyl)2-cyclohexen-1-yl pivalate (cis-18-OPiv) with LiCuBu2, LiCuPh2, and LiCu(CN) ph gives only alpha-coupling product; with LiCu(CN)Bu, a mixture of alpha, gamma, and epsilon coupling product was obtained. Cross coupling with LiCuBu2, results in loss of double-bond configuration in the alpha-alkylation product. With the other cuprates, no loss of double-bond configuration was detected in the alpha and gamma coupling product. These results have profound mechanistic implications, which are discussed. The relationship between structure and reactivity was also investigated. A variety of diallylic pivalates (1-5 OPiv) were prepared and cross coupled with LiCuBu2, LiCu(CN)Bu, LiCuPh2, and LiCu(CN)Ph. Generally, coupling occurs at the least-substituted allylic system; mechanistic implications are discussed.

  DOI：

  10.1021/jo00007a055

文献信息

• Palladium-catalyzed cross-coupling reactions of organogold(i) phosphanes with allylic electrophiles
  作者：Miguel Peña-López、Miguel Ayán-Varela、Luis A. Sarandeses、José Pérez Sestelo

  DOI：10.1039/c2ob06788a

  日期：——

  as cinnamyl and geranyl halides (bromide, chloride and acetates) under palladium catalysis in THF at 80 °C to afford the α-substitution product with moderate to high yields. When the reaction is performed with a chiral enantiopure secondary acetate, the α-substituted cross-coupling product is obtained with complete inversion of the stereochemistry.

  芳基和链烯基金（I）膦在钯催化下于80°C在THF中于80°C下与烯丙基亲电试剂如肉桂基和香叶基卤化物（溴化物，氯化物和乙酸盐）发生区域选择性反应，以中等至高收率获得α取代产物。当用手性对映体纯的仲乙酸酯进行反应时，在立体化学完全转化的情况下获得了α-取代的交叉偶联产物。
• Aminium Salts Induced Desulphurization of Allyl and Diallyl Thiiranes. Synthesis of Dienes and Trienes
  作者：Vincenzo Caló、Luigi Lopez、Angelo Nacci、Giuseppe Mele

  DOI：10.1016/0040-4020(95)00502-y

  日期：1995.8

  conversion of methylene chloride in solutions of several allyl and diallyl episulphides 1–6 into the corresponding unsaturated derivatives 7–12. The desulphurization process, which occurs through a plausible chain electron-transfer mechanism, rapid and may proceed in a fashion that preserves the stereochemistry of the starting episulphide.

  催化量的铵盐AB会诱导二氯甲烷在几种烯丙基和二烯丙基环氧乙烷1–6的溶液中转化为相应的不饱和衍生物7–12。脱硫过程是通过合理的链电子转移机制而迅速进行的，并且可能以保留起始硫化物的立体化学的方式进行。
• Brenner,S.; Klein,J., Israel Journal of Chemistry, 1969, vol. 7, p. 735 - 740
  作者：Brenner,S.、Klein,J.

  DOI：——

  日期：——
• Stereoselective synthesis of 1,4-dienes by chelation-controlled reduction of benzothiazole β-oxosulfides
  作者：Vincenzo Caló、Angelo Nacci

  DOI：10.1016/s0040-4039(98)00622-4

  日期：1998.5

  Allylated beta-oxosulfides of benzothiazole can replace beta-oxophosphane oxides to provide a stereospecific alkene synthesis. These sulfides, by reduction with sodium borohydride afford predominantly syn beta-hydroxy sulfides. DIBAL reduction in the presence of magnesium bromide improves the syn stereomer formation. Base treatment of these beta-hydroxy sulfides affords (Z)-allyl thiiranes which are converted into (E, Z)-dienes. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Alkylation of allylic derivatives. 17. Cross-coupling reactions of diallylic pivalates with butyl- and phenylcopper reagents
  作者：Ted L. Underiner、Harlan L. Goering

  DOI：10.1021/jo00007a055

  日期：1991.3

  Cross coupling (Z)-1-phenyl-1,4-pentadien-3-yl pivalate (cis-1-OPiv) with LiCuBu2, LiCu(CN)Bu, LiCuPh2, and LiCu(CN)Ph gives only the fully conjugated gamma-coupling product. With LiCuBu2, substantial loss of double-bond configuration occurs to give primarily the all-trans coupling product. With other cuprates, no detectable loss of double-bond configuration was observed. Cross coupling (Z)-3-(2-phenylethenyl)2-cyclohexen-1-yl pivalate (cis-18-OPiv) with LiCuBu2, LiCuPh2, and LiCu(CN) ph gives only alpha-coupling product; with LiCu(CN)Bu, a mixture of alpha, gamma, and epsilon coupling product was obtained. Cross coupling with LiCuBu2, results in loss of double-bond configuration in the alpha-alkylation product. With the other cuprates, no loss of double-bond configuration was detected in the alpha and gamma coupling product. These results have profound mechanistic implications, which are discussed. The relationship between structure and reactivity was also investigated. A variety of diallylic pivalates (1-5 OPiv) were prepared and cross coupled with LiCuBu2, LiCu(CN)Bu, LiCuPh2, and LiCu(CN)Ph. Generally, coupling occurs at the least-substituted allylic system; mechanistic implications are discussed.