二甲基十六碳-8-烯二酸酯 | 57568-17-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 二甲基十六碳-8-烯二酸酯
• 英文名称: dimethyl hexadec-8-enedioate
• 英文别名: Dimethyl hexadec-8-enedioate
• CAS: 57568-17-9
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: QYWUBHYFAJOUTO-UHFFFAOYSA-N

物化性质

• 沸点：
  389.1±35.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二甲基十六碳-8-烯二酸酯 在 乙烯 、 [2-(1-methylethoxy-κO)phenylmethyl-κC](nitrato-κO,κO′){rel-(2R,5R,7S)-tricyclo[3.3.1.1^3,7]decane-2,1-diyl[3-(2,4,6-trimethylphenyl)-1-imidazolidinyl-2-ylidene]}ruthenium 作用下， 以 四氢呋喃 为溶剂， 35.0 ℃ 、506.66 kPa 条件下， 反应 6.0h， 以90%的产率得到
  参考文献：
  名称：

  Z-Selective Ethenolysis with a Ruthenium Metathesis Catalyst: Experiment and Theory

  摘要：

  The Z-selective ethenolysis activity of chelated ruthenium metathesis catalysts was investigated with experiment and theory. A five-membered chelated catalyst that was successfully employed in Z-selective cross metathesis reactions has now been found to be highly active for Z-selective ethenolysis at low ethylene pressures, while tolerating a wide variety of functional groups. This phenomenon also affects its activity in cross metathesis reactions and prohibits crossover reactions of internal olefins via trisubstituted ruthenacyclobutane intermediates. In contrast, a related catalyst containing a six-membered chelated architecture is not active for ethenolysis and seems to react through different pathways more reminiscent of previous generations of ruthenium catalysts. Computational investigations of the effects of substitution on relevant transition states and ruthenacyclobutane intermediates revealed that the differences of activities are attributed to the steric repulsions of the anionic ligand with the chelating groups.

  DOI：

  10.1021/ja4010267
• 作为产物：
  描述：

  8-decenoic acid methyl ester 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 生成 2-丁烯 、 二甲基十六碳-8-烯二酸酯
  参考文献：
  名称：

  [EN] METHODS OF MAKING FUNCTIONALIZED INTERNAL OLEFINS AND USES THEREOF
  [FR] PROCÉDÉS DE FABRICATION D'OLÉFINES INTERNES FONCTIONNALISÉES ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2014085393A9

文献信息

• [EN] METHODS OF MAKING FUNCTIONALIZED INTERNAL OLEFINS AND USES THEREOF<br/>[FR] PROCÉDÉS DE FABRICATION D'OLÉFINES INTERNES FONCTIONNALISÉES ET LEURS UTILISATIONS
  申请人：ELEVANCE RENEWABLE SCIENCES

  公开号：WO2014085393A9

  公开（公告）日：2014-11-06
• <i>Z</i>-Selective Ethenolysis with a Ruthenium Metathesis Catalyst: Experiment and Theory
  作者：Hiroshi Miyazaki、Myles B. Herbert、Peng Liu、Xiaofei Dong、Xiufang Xu、Benjamin K. Keitz、Thay Ung、Garik Mkrtumyan、K. N. Houk、Robert H. Grubbs

  DOI：10.1021/ja4010267

  日期：2013.4.17

  The Z-selective ethenolysis activity of chelated ruthenium metathesis catalysts was investigated with experiment and theory. A five-membered chelated catalyst that was successfully employed in Z-selective cross metathesis reactions has now been found to be highly active for Z-selective ethenolysis at low ethylene pressures, while tolerating a wide variety of functional groups. This phenomenon also affects its activity in cross metathesis reactions and prohibits crossover reactions of internal olefins via trisubstituted ruthenacyclobutane intermediates. In contrast, a related catalyst containing a six-membered chelated architecture is not active for ethenolysis and seems to react through different pathways more reminiscent of previous generations of ruthenium catalysts. Computational investigations of the effects of substitution on relevant transition states and ruthenacyclobutane intermediates revealed that the differences of activities are attributed to the steric repulsions of the anionic ligand with the chelating groups.