ethyl (E)-4-(ethoxycarbonyloxy)-2-nonenoate | 157670-37-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-4-(ethoxycarbonyloxy)-2-nonenoate
• 英文别名: ethyl (E)-4-ethoxycarbonyloxynon-2-enoate
• CAS: 157670-37-6
• 化学式: C₁₄H₂₄O₅
• 分子量: 272.342
• InChiKey: IUZYZLHTUSNUNV-ZHACJKMWSA-N

物化性质

• 沸点：
  337.9±35.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (E)-4-(ethoxycarbonyloxy)-2-nonenoate 、 Lithium;furan-2-yl(trimethoxy)boranuide 以67%的产率得到
  参考文献：
  名称：

  Kobayashi Yuichi, Ikeda Eitatsu, J. Chem. Soc. Chem. Commun, (1994) N 15, S 1789- 1790

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-1-iodooct-1-en-3-ol 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl (E)-4-(ethoxycarbonyloxy)-2-nonenoate
  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。