2-benzyl-1,4-pentadiene | 126300-47-8

• 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: 2-benzyl-1,4-pentadiene
• 英文别名: Benzene, (2-methylene-4-pentenyl)-；2-methylidenepent-4-enylbenzene
• CAS: 126300-47-8
• 化学式: C₁₂H₁₄
• 分子量: 158.243
• InChiKey: ZWQKTPBTNMBXTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  2-benzyl-1,4-pentadiene 在 二氯[2，2’-二(二苯基磷)-1，1’-联萘]钯(II) 9-borabicyclo[3.3.1]nonane dimer 、 potassium fluoride 、 2-氯-2-苯基苯乙酮 作用下， 以 四氢呋喃 、 水 为溶剂， 以42%的产率得到环戊基苯基甲烷
  参考文献：
  名称：

  两个Csp（3）-Csp（3）中心之间的钯催化均偶联反应。

  摘要：

  [反应：见正文]已经研究了两个Csp（3）-Csp（3）中心之间的新型钯催化的偶联反应。该协议是通过将α-卤代羰基化合物氧化添加到钯（0）物种中引发的，然后进行双金属转移。关键的二烷基钯中间体经过还原消除，以形成所需的偶联产物。

  DOI：

  10.1021/ol0258536
• 作为产物：
  描述：

  2-(2-benzyl-2-hydroxy-4-pentenylseleno)benzothiazole 在 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以82%的产率得到2-benzyl-1,4-pentadiene
  参考文献：
  名称：

  Shibata, Koichi; Shiono, Hirofumi; Mitsunobu, Oyo, Chemistry Letters, 1991, # 4, p. 661 - 664

  摘要：

  DOI：

文献信息

• Preparation of 1,4-Dienes from 2-(2-Hydroxyalkylseleno)benzothiazoles by the Reaction Involving Se → O Azaaromatic Ring Rearrangement
  作者：Koichi Shibata、Oyo Mitsunobu

  DOI：10.1246/bcsj.65.3163

  日期：1992.11

  The reactions of 2-(2-oxoalkylseleno)benzothiazoles with allylic Grignard reagents in the presence of BF3·OEt2 gave the corresponding 2-[(2-alkyl-2-hydroxy-4-pententyl or 2-alkyl-2-hydroxy-4-methyl-4-pentenyl)seleno]benzothiazoles which, on treatment with Ph3P and NaH, afforded 1,4-dienes in good to excellent yields.

  在BF3·OEt2存在的条件下，2-（2-氧代烷基硒）苯并噻唑与烯丙基格氏试剂反应，生成相应的2-[(2-烷基-2-羟基-4-戊烯基或2-烷基-2-羟基-4-甲基-4-戊烯基)硒]苯并噻唑，这些化合物在Ph3P和NaH处理后，能以良好至优异的产率得到1,4-二烯。
• Regioselective allylgallation of terminal alkynes
  作者：Phil Ho Lee、Yunkiu Heo、Dong Seomoon、Sundae Kim、Kooyeon Lee

  DOI：10.1039/b417975g

  日期：——

  The reactions of terminal alkynes with allylgallium reagents generated in situ from gallium and allyl bromides gave the corresponding 1,4-dienes in good yield via Markovnikov addition in THF at 70 °C.

  终端炔烃与现场生成的烯丙基镓试剂（由镓和烯丙基溴化物反应生成）在THF中于70°C进行Markovnikov加成反应，得到相应的1,4-二烯，产率良好。
• Allylic organobismetallic reagents - part 2
  作者：J.F. Normant、J.Ch. Quirion

  DOI：10.1016/s0040-4039(00)99294-3

  日期：1989.1
• Allylation of Unactivated and/or Functionalized Alkynes with Allylindiums
  作者：Naoya Fujiwara、Yoshinori Yamamoto

  DOI：10.1021/jo9701041

  日期：1997.4.1
• Allyl- and Benzylindium Reagents. Carboindation of Carbon−Carbon and Carbon−Nitrogen Triple Bonds
  作者：Naoya Fujiwara、Yoshinori Yamamoto

  DOI：10.1021/jo990160x

  日期：1999.5.1

  The reaction of unactivated simple terminal alkynes 1 with allylindiums in THF proceeded smoothly to give the corresponding allylation products 2 in good to high yields. This result is in marked contrast to that of the reaction carried out in DMF, where the allylation of unactivated alkynes was very sluggish. The allylic group of the reagent was attached to the internal carbon of the triple. bond, and indium was attached to the less substituted terminal carbon, except for the case of TMS substituted acetylenes 1j and 1k in which the allyl group went to the less substituted carbon of the triple band. The reaction of unactivated simple terminal and certain internal acetylenes with benzylindium in THF proceeded smoothly to afford the corresponding benzylation products 18 in good to high yields. The benzyl group was attached to the less substituted unhindered carbon of the triple bond, and indium was attached to the more sterically congested carbon. The reaction of activated nitriles 3 with allylindiums in THF at 70 degrees C gave the corresponding allylation-enamination products 4 in high to excellent yields. This reaction provides a useful method for the synthesis of highly functionalized enamines, which are not easily available via conventional methods. The mechanisms on the above three indation reactions are discussed.