1,5-diphenyl-1-pentene | 7433-54-7

• 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: 1,5-diphenyl-1-pentene
• 英文别名: 1.5-Diphenylpenten-(1)；1,5-diphenyl-pent-1-ene；1,5-Diphenyl-pent-1-en；5-phenylpent-1-enylbenzene
• CAS: 7433-54-7
• 化学式: C₁₇H₁₈
• 分子量: 222.33
• InChiKey: KENSKKQCGCEMPH-UHFFFAOYSA-N

物化性质

• 沸点：
  186 °C(Press: 11 Torr)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• 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

• 作为产物：
  描述：

  (2R,6S)-2,6-diphenylpiperidine 在 盐酸 、 lithium aluminium tetrahydride 、 乙醚 、 乙醇 、 水 、 mercury(II) oxide 、 sodium nitrite 作用下， 生成 1,5-diphenyl-1-pentene
  参考文献：
  名称：

  Overberger et al., Journal of the American Chemical Society, 1957, vol. 79, p. 6430,6435

  摘要：

  DOI：

文献信息

• Palladium(0)-Catalyzed Cross-Coupling of 1,1-Diboronates with Vinyl Bromides and 1,1-Dibromoalkenes
  作者：Huan Li、Zhikun Zhang、Xianghang Shangguan、Shan Huang、Jun Chen、Yan Zhang、Jianbo Wang

  DOI：10.1002/anie.201407000

  日期：2014.10.27

  Palladium‐catalyzed cross‐coupling reactions of 1,1‐diboronates with vinyl bromides and dibromoalkenes were found to afford 1,4‐dienes and allenes, respectively. These reactions utilize the high reactivities of both 1,1‐diboronates and allylboron intermediates generated in the initial coupling.

  发现1,1-二硼酸酯与乙烯基溴化物和二溴代烯烃的钯催化交叉偶联反应分别得到1,4-二烯和丙二烯。这些反应利用了在初始偶联过程中产生的1,1-二硼酸酯和烯丙基硼中间体的高反应活性。
• Copper-Free Asymmetric Allylic Alkylation with Grignard Reagents
  作者：Olivier Jackowski、Alexandre Alexakis

  DOI：10.1002/anie.201000577

  日期：2010.4.26

  Open wide and say AAA: The copper‐free asymmetric allylic alkylation reaction of Grignard reagents, catalyzed by N‐heterocyclic carbenes, is reported for allyl bromide derivatives. This reaction offers good enantioselectivity and good to excellent γ regioselectivity, particularly for the formation of quaternary chiral centers (see scheme; Mes=mesityl).

  张开嘴说AAA：据报道，N-杂环卡宾催化了格氏试剂的无铜不对称烯丙基烷基化反应，是烯丙基溴衍生物的反应。该反应提供了良好的对映选择性和良好的至优异的γ区域选择性，特别是对于形成四元手性中心（参见方案； Mes ＝甲磺酰基）。
• Recyclable and reusable PdCl₂(PPh₃)₂/PEG-400/H₂O system for the hydrophenylation of alkynes with sodium tetraphenylborate
  作者：Rong Liu、Tingli Zhang、Bin Huang、Mingzhong Cai

  DOI：10.1177/1747519820934379

  日期：2021.1

  A stable and efficient PdCl₂(PPh₃)₂/PEG-400/H₂O catalytic system for the hydrophenylation reaction of alkynes has been developed. In the presence of 3 mol% PdCl₂(PPh₃)₂ and 2 equiv. of HOAc, the hydrophenylation of both terminal and internal alkynes with sodium tetraphenylborate proceeded smoothly in a mixture of PEG-400 and water at room temperature or 50 °C to afford a variety of phenyl-substituted alkenes in moderate to high yields. The isolation of the products was easily performed by extraction with petroleum ether, and the PdCl₂(PPh₃)₂/PEG-400/H₂O system could be readily recycled and reused six times without apparent loss of catalytic activity.

  已开发出一种稳定高效的PdCl₂(PPh₃)₂/PEG-400/H₂O催化体系，用于炔烃的加氢苯基化反应。在存在3 mol% PdCl₂(PPh₃)₂和2当量的HOAc的情况下，终末和内部炔烃与四苯硼酸钠在PEG-400和水的混合物中在室温或50 °C下顺利进行了苯基化反应，产率中等到较高。 产品的分离可通过石油醚萃取轻松进行，PdCl₂(PPh₃)₂/PEG-400/H₂O体系可轻松回收和重复使用六次而无明显失活。
• The direct formation of functionalized alkyl(aryl)zinc halides by oxidative addition of highly reactive zinc with organic halides and their reactions with acid chlorides, .alpha.,.beta.-unsaturated ketones, and allylic, aryl, and vinyl halides
  作者：Lishan Zhu、Richard M. Wehmeyer、Reuben D. Rieke

  DOI：10.1021/jo00004a021

  日期：1991.2

  Highly reactive zinc, prepared by the lithium naphthalenide reduction of ZnCl2, readily undergoes oxidative addition to alkyl, aryl, and vinyl halides under mild conditions to generate the corresponding organozinc compounds in excellent yields. Significantly, the reaction will tolerate a spectrum of functional groups on the organic halides. Accordingly, this approach can now be used to prepare a wide variety of highly functionalized organozinc compounds. In the presence of Cu(I) salts, the organozinc compounds cross-couple with acid chlorides, conjugatively add to alpha,beta-unsaturated ketones, and regioselectively undergo S(N)2' substitution reactions with allylic halides. They also cross-couple with aryl or vinyl halides with Pd(0) catalysts.
• Borsche; Wollemann, Chemische Berichte, 1912, vol. 45, p. 3717
  作者：Borsche、Wollemann

  DOI：——

  日期：——