(2E)-1-phenyloct-2-en-1-ol | 181229-27-6

• 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: (2E)-1-phenyloct-2-en-1-ol
• 英文别名: (E)-1-phenyl-2-octen-1-ol；(E)-1-phenyloct-2-en-1-ol
• CAS: 181229-27-6
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: MNMUVJMOYJVSRF-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E)-1-phenyloct-2-en-1-ol 在 吡啶 、 (1,1'-双(二苯基膦)二茂铁)二氯化镍 、 甲基锂 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (E)-1-phenyl-3-((E)-2-phenylethenyl)-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
• 作为产物：
  描述：

  (E)-1-phenyl-2-octen-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (2E)-1-phenyloct-2-en-1-ol
  参考文献：
  名称：

  通过sa（II）介导的烯丙基苯甲酸酯的消除/异构化选择性形成非共轭烯烃

  摘要：

  可以通过二碘化ates的作用将芳族烯丙基苯甲酸酯选择性地转化为相应的苯甲酸酯消除的烯烃。取决于底物和消除条件，可以实现对非共轭烯烃产物的高选择性。

  DOI：

  10.1016/j.tetlet.2013.08.136

文献信息

• Stereoselective synthesis of either (E)- or (Z)-silyl enol ether from the same acyclic α,β-unsaturated ketone using cationic rhodium complex-catalyzed 1,4-hydrosilylation
  作者：Gen Onodera、Ryosuke Hachisuka、Tomomi Noguchi、Hiroki Miura、Toru Hashimoto、Ryo Takeuchi

  DOI：10.1016/j.tetlet.2013.10.085

  日期：2014.1

  The stereoselective synthesis of either (E)- or (Z)-silyl enol ether from the same acyclic α,β-unsaturated ketone is reported. Highly (Z)-selective conditions were the use of [Rh(cod)2]BF4/DPPE at room temperature with no solvent, whereas (E)-selective conditions were the use of [Rh(cod)2]BF4/P(1-Nap)3 (1-Nap = 1-naphthyl) under refluxing dichloromethane.

  据报道从相同的无环α，β-不饱和酮立体合成（E）-或（Z）-甲硅烷基烯醇醚。高度（Z）选择性条件是在室温下无溶剂下使用[Rh（cod）2 ] BF 4 / DPPE，而（E）选择性条件是使用[Rh（cod）2 ] BF 4 /在回流的二氯甲烷下，P（1-Nap）3（1-Nap ＝ 1-萘基）。
• Tandem Benzylic Oxidation/Dihydroxylation of<i>α</i>-Vinyl- and<i>α</i>-Alkenylbenzyl Alcohols
  作者：Rodney A. Fernandes、Pullaiah Kattanguru

  DOI：10.1002/hlca.201400143

  日期：2015.1

  A de novo tandem benzylic oxidative dihydroxylation of α‐vinyl‐ and α‐alkenylbenzyl alcohols has been developed to give α,β‐dihydroxypropiophenones (=2,3‐dihydroxy‐1‐phenylpropan‐1‐ones) and α,β‐dihydroxyalkyl phenones. This method was shown to be substrate‐selective and specific for the oxidation of benzylic alcohols.

  甲从头的串联苄氧化二羟基α -vinyl-和α -alkenylbenzyl醇已被开发，得到α，β -dihydroxypropiophenones（= 2,3-二羟基-1-苯基丙-1-酮）和α，β -dihydroxyalkyl苯酮。该方法显示出对底物有选择性，并且对苯甲醇的氧化具有特异性。
• Selective formation of non-conjugated olefins by samarium(II)-mediated elimination/isomerization of allylic benzoates
  作者：Sara L. Schaefer、Connor L. Roberts、Erasmus O. Volz、Monika R. Grasso、Gregory W. O’Neil

  DOI：10.1016/j.tetlet.2013.08.136

  日期：2013.11

  Aromatic allylic benzoates can be selectively transformed to the corresponding benzoate eliminated olefin by the action of samarium diiodide. Depending on the substrate and the elimination conditions, high selectivity for the non-conjugated alkene product can be achieved.

  可以通过二碘化ates的作用将芳族烯丙基苯甲酸酯选择性地转化为相应的苯甲酸酯消除的烯烃。取决于底物和消除条件，可以实现对非共轭烯烃产物的高选择性。
• 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.