(E)-methyl cyclooct-1-enecarboxylate | 62995-25-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-methyl cyclooct-1-enecarboxylate
• 英文别名: 1-(methoxycarbonyl)cyclooctene；methyl cyclooctenecarboxylate；cyclooct-1c-enecarboxylic acid methyl ester；Cyclooct-1c-encarbonsaeure-methylester；methyl 1-cyclooctene-1-carboxylate；1-Cyclooctencarbonsaeure-methylester；1-Cyclooctene-1-carboxylic acid, methyl ester；methyl (1E)-cyclooctene-1-carboxylate
• CAS: 62995-25-9
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: BGHGZCBTTXFJLV-VQHVLOKHSA-N

物化性质

• 沸点：
  74-75 °C(Press: 1.5 Torr)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-methyl cyclooct-1-enecarboxylate 、 联硼酸频那醇酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 三苯胂 作用下， 以 正辛烷 为溶剂， 反应 16.17h， 以35%的产率得到(E)-methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclooct-1-enecarboxylate
  参考文献：
  名称：

  Iridium(i)-catalyzed vinylic C–H borylation of 1-cycloalkenecarboxylates with bis(pinacolato)diboron

  摘要：

  Ir(I)催化的带有双(频哪醇)二硼的1-环烯羧酸衍生物的C-H硼化反应，以优异的产率得到各种带有功能基团的烯基�硼酸盐。该反应还用于一步法硼化/铃木-宫浦交叉偶联程序。

  DOI：

  10.1039/c3cc44149k
• 作为产物：
  描述：

  环辛烷羰基氯化物 在 喹啉 、 磷化氢 、 溴 作用下， 反应 2.0h， 生成 (E)-methyl cyclooct-1-enecarboxylate
  参考文献：
  名称：

  Iridium(i)-catalyzed vinylic C–H borylation of 1-cycloalkenecarboxylates with bis(pinacolato)diboron

  摘要：

  Ir(I)催化的带有双(频哪醇)二硼的1-环烯羧酸衍生物的C-H硼化反应，以优异的产率得到各种带有功能基团的烯基�硼酸盐。该反应还用于一步法硼化/铃木-宫浦交叉偶联程序。

  DOI：

  10.1039/c3cc44149k

文献信息

• α,β-Epoxy Sulfoxides as Useful Intermediates in Organic Synthesis. X. An Improved Synthesis of α,β-Unsaturated Carbonyl Compounds from Carbonyl Compounds with Carbon Homologation through α,β-Epoxy Sulfoxides
  作者：Tsuyoshi Satoh、Masayuki Itoh、Teruhiko Ohara、Koji Yamakawa

  DOI：10.1246/bcsj.60.1839

  日期：1987.5

  derived from ketones and chloromethyl phenyl sulfoxide or 1-chloroalkyl phenyl sulfoxides with lithium perchlorate in the presence of tributylphosphine oxide in toluene at 110 °C for about 1–3 h gave α,β-unsaturated aldehydes or α,β-unsaturated ketones in high yields. In contrast to these results, the α,β-epoxy sulfoxides derived from aldehydes did not give the desired α,β-unsaturated ketones. In this

  在三丁基氧化膦的存在下，在甲苯中，在 110 °C 的条件下，用高氯酸锂处理衍生自酮和氯甲基苯亚砜或 1-氯烷基苯亚砜的 α,β-环氧亚砜约 1-3 小时，得到 α,β-不饱和醛或高产率的 α,β-不饱和酮。与这些结果相反，衍生自醛的 α,β-环氧亚砜没有得到所需的 α,β-不饱和酮。在这种情况下，用苯硫醇和间氯过苯甲酸依次处理 α,β-环氧亚砜，得到 α-苯基亚磺酰化酮，将其在 110°C 的甲苯中加热，以良好的总产率得到所需的烯酮。通过该方法获得的α,β-不饱和醛的氧化以高产率得到α,β-不饱和羧酸。
• A New Indirect Application of Aggregative Activation: Synthesis of Esters by Cobalt-Catalyzed Carbonylation of Aryl, Heterocyclic, and Vinyl Halides under Atmospheric Pressure
  作者：Joel Marchal、Jacques Bodiguel、Yves Fort、Paul Caubere

  DOI：10.1021/jo00131a005

  日期：1995.12

  Sun lamp illuminated alkoxycarbonylation of aryl, heteroaryl, and vinyl halides was performed under atmospheric pressure of CO in the presence of a cobalt catalyst in situ generated from Co(OAc)(2). Illumination through a Pyrex flask was sufficient to catalyze the reaction. This process avoids the use of Co-2(CO)(8) and excess CH3I, which were required in the earlier procedure. A S-RN(1) mechanism is proposed.
• Brønsted acidic ionic liquid as an efficient and recyclable promoter for hydroesterification of olefins catalyzed by a triphenylphosphine–palladium complex
  作者：Jing Yang、Hancheng Zhou、Xinning Lu、Youzhu Yuan

  DOI：10.1016/j.catcom.2010.05.025

  日期：2010.9

  Several Bronsted acidic ionic liquids (BAILs) with different acidic scales were synthesized and employed as acid promoters for the hydroesterification of olefins catalyzed by a triphenylphosphine-palladium complex. The results showed that catalysts with BAIL promoters resulted in moderate to high conversions to the ester product with excellent selectivity, depending on the acidity of BAIL used. The reaction conversion reached a plateau when the catalyst was promoted using BAIL with a Hammett acidity function less than or equal to -0.11. This catalyst system could be reused several times for the hydroesterification of 1-hexene without a considerable decrease in the catalytic performance. (C) 2010 Elsevier B.V. All rights reserved.
• Proximity Effects. XV. The Reaction of Phenylmagnesium Bromide with Methyl Cycloöctene-1-carboxylate
  作者：Arthur C. Cope、Morton Brown

  DOI：10.1021/ja01544a067

  日期：1958.6
• POLYMER AND SOLAR ENCAPSULANT USING SAME
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2781531B1

  公开（公告）日：2017-07-12