(E)-1,3-diphenyl-1-octene

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (E)-1,3-diphenyl-1-octene
• 英文别名: [(E)-1-phenyloct-1-en-3-yl]benzene
• 化学式: C₂₀H₂₄
• 分子量: 264.411
• InChiKey: NIZOUMVDQVRQDG-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  反-2-辛烯醛 在 吡啶 、 (1,1'-双(二苯基膦)二茂铁)二氯化镍 、 甲基锂 作用下， 以 乙醚 、 二氯甲烷 、 环己烷 为溶剂， 反应 12.42h， 生成 (E)-1,3-diphenyl-1-octene
  参考文献：
  名称：

  Nickel-Catalyzed Coupling Reaction of 1,3-Disubstituted Secondary Allylic Carbonates and Lithium Aryl- and Alkenylborates

  摘要：

  This account describes coupling reaction of 1,3-disubstituted secondary allylic carbonates with lithium aryl- and alkenylborates in the presence of a nickel. catalyst. Berates examined are 4, 5, and 6, and reactivity and selectivity were investigated using the allylic carbonates la and Ib. Coupling of la,b with berates 4 was effected with the nickel catalyst, NiCl2(PPh(3))(2) or NiCl2(dppf), in THF at 45-65 degrees C to provide products 3 in good yields with almost 100% regio- and stereoselectivities. Trivalent organoboranes prepared from acetylenes by hydroboration with catecholborane also underwent coupling reaction with la,b after transformation to berates 5 with MeLi. Though coupling using 4 and 5 required elevated temperature (45-65 degrees C), cyclic berates 6 prepared in situ from boronates 8 and MeLi were found to couple with la,b at room temperature or below. Regio- and stereoselectivities were almost 100% as were observed in the cases of 4 and 5. In these reactions, palladium complexes such as Pd(PPh(3))(4), Pd-2(dba)(3) . CHCl3 + 2 PPh(3) showed no catalytic activity. Stereochemical aspect of the present reaction was studied using cyclohexenyl carbonate 24 with 2-furylborate 4e and phenylborate 6a, and was found to proceed with overall anti fashion. With additional experiments, the mechanism of the present reaction was discussed in terms of transient pi-allylnickel intermediates.

  DOI：

  10.1021/jo960458c

文献信息

• Nickel-catalysed substitution reactions of allylic carbonates with aryl- and alkenyl-borates
  作者：Yuichi Kobayashi、Eitatsu Ikeda

  DOI：10.1039/c39940001789

  日期：——

  Substitution reactions of 1,3-disubstituted allylic carbonates 3 with aryl- and alkenyl-borates 4 are catalysed by [NiCl2(dppf)][dppf = 1,1′-bis(diphenylphosphino)ferrocene], and in the case of the cyclic carbonate 7, the reaction proceeds with complete inversion.

  1,3-二取代的烯丙基碳酸酯 3 与芳基和烯基硼酸盐 4 的取代反应在 [NiCl2(dppf)] 的催化下进行，其中 dppf = 1,1′-双(二苯基膦)铁烯， 在环状碳酸酯 7 的情况下，该反应完全反转进行。
• Development of zinc borates designed for functionalized hard nucleophiles in the coupling reaction with allylic alcohol derivatives
  作者：Yuichi Kobayashi、Kengo Watatani、Yuko Tokoro

  DOI：10.1016/s0040-4039(98)01638-4

  日期：1998.10

  Zinc borates 3 (RT = aryl, alkenyl), prepared from the boronate esters 1 and MeZnCl, were developed for the title reaction. Thus, reaction of the allylic acetates 6a-c with the aryl borates 3a-f and the alkenyl borates 3g,h in the presence of NiCl2(PPh3)2 (10 mol%) and DMI (10 equiv) at 40–50 °C afforded the coupling products 8a-o in good yields (Tables 1 and 2). Since MeZnCl is almost inert toward

  由硼酸酯1和MeZnCl制备的硼酸锌3（R T＝芳基，烯基）被开发用于标题反应。因此，在40–50的NiCl 2（PPh 3）2（10 mol％）和DMI（10当量）存在下，烯丙基乙酸酯6a-c与芳基硼酸酯3a-f和烯基硼酸酯3g，h反应℃以良好的收率得到偶联产物8a-o（表1和2）。由于MeZnCl对羰基几乎是惰性的，因此该方法适用于官能化硼酸盐3。
• Zinc Borates: Functionalized Hard Nucleophiles for Coupling Reactions with Secondary Allylic Acetates
  作者：Yuichi Kobayashi、Yuko Tokoro、Kengo Watatani

  DOI：10.1002/1099-0690(200012)2000:23<3825::aid-ejoc3825>3.3.co;2-7

  日期：2000.12
• Kobayashi Yuichi, Ikeda Eitatsu, J. Chem. Soc. Chem. Commun, (1994) N 15, S 1789- 1790
  作者：Kobayashi Yuichi, Ikeda Eitatsu

  DOI：——

  日期：——
• Nickel-Catalyzed Coupling Reaction of 1,3-Disubstituted Secondary Allylic Carbonates and Lithium Aryl- and Alkenylborates
  作者：Yuichi Kobayashi、Ryo Mizojiri、Eitatsu Ikeda

  DOI：10.1021/jo960458c

  日期：1996.1.1

  This account describes coupling reaction of 1,3-disubstituted secondary allylic carbonates with lithium aryl- and alkenylborates in the presence of a nickel. catalyst. Berates examined are 4, 5, and 6, and reactivity and selectivity were investigated using the allylic carbonates la and Ib. Coupling of la,b with berates 4 was effected with the nickel catalyst, NiCl2(PPh(3))(2) or NiCl2(dppf), in THF at 45-65 degrees C to provide products 3 in good yields with almost 100% regio- and stereoselectivities. Trivalent organoboranes prepared from acetylenes by hydroboration with catecholborane also underwent coupling reaction with la,b after transformation to berates 5 with MeLi. Though coupling using 4 and 5 required elevated temperature (45-65 degrees C), cyclic berates 6 prepared in situ from boronates 8 and MeLi were found to couple with la,b at room temperature or below. Regio- and stereoselectivities were almost 100% as were observed in the cases of 4 and 5. In these reactions, palladium complexes such as Pd(PPh(3))(4), Pd-2(dba)(3) . CHCl3 + 2 PPh(3) showed no catalytic activity. Stereochemical aspect of the present reaction was studied using cyclohexenyl carbonate 24 with 2-furylborate 4e and phenylborate 6a, and was found to proceed with overall anti fashion. With additional experiments, the mechanism of the present reaction was discussed in terms of transient pi-allylnickel intermediates.