(E)-癸-5-烯二酸 | 39516-91-1

• 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: (E)-癸-5-烯二酸
• 英文名称: 5-decenedioic acid
• 英文别名: Dec-5-en-disaeure；1,8-Octen-4-dicarbonsaeure；4-Octen-1,8-dicarboxylic acid；dec-5-enedioic acid
• CAS: 39516-91-1
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: WAGQZQAZCIOEDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2917190090

反应信息

• 作为产物：
  描述：

  5-己烯酸 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 1,1-二甲基-1-硅-2-噁环己烷 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以87%的产率得到(E)-癸-5-烯二酸
  参考文献：
  名称：

  Occlusion of Grubbs' Catalysts in Active Membranes of Polydimethylsiloxane:  Catalysis in Water and New Functional Group Selectivities

  摘要：

  The Grubbs' first and second generation catalysts were occluded into cross-linked slabs of polydimethylsiloxane with volumes from 1 mm3 to 1 cm3 by swelling the polymer with catalyst and methylene chloride. Methylene chloride was evaporated under vacuum to yield occluded catalysts where their solvent was polydimethylsiloxane. These occluded catalysts were reacted with alkenes dissolved in H2O or H2O/MeOH mixtures that diffused into the polydimethylsiloxane to react by ring-closing metathesis and cross metathesis. Control experiments revealed that the catalysts remained occluded and metathesis did not occur in the solvent. Occlusion of these catalysts allowed commercially available Grubbs' catalysts to be used with H2O as the solvent while isolating the H2O sensitive ruthenium methylidene from exposure to H2O. Functional group selective experiments were carried out where the polydimethylsiloxane was an "active" membrane to exclude salts. Polydimethylsiloxane is a hydrophobic polymer, so the deprotonated salt of diallylmalonic acid did not diffuse into it while a diallylether diffused into it and reacted by metathesis. Thus, by controlling the polarity of reagents their reactivity can be controlled owing to the properties of polydimethylsiloxane rather than those of the Grubbs' catalysts. Occlusion of catalysts in polydimethylsiloxane has been shown to add new selectivities to mature catalysts.

  DOI：

  10.1021/ja0642212

文献信息

• Microalgae lipids as a feedstock for the production of benzene
  作者：Dennis Pingen、Julia Zimmerer、Nele Klinkenberg、Stefan Mecking

  DOI：10.1039/c8gc00423d

  日期：——

  unsaturated fatty acid eicosapentaenoic acid (EPA), a component of microalgae oils, is presented. By a sequence of olefin metathesis and the catalytic dehydrogenation of the resulting 1,4-cyclohexadiene, two equivalents of benzene are effectively formed per EPA substrate molecule. As the only major by-products, 5-octenoic acid and 5-decenedioic acid are formed. Performing the dehydrogenation step under hydrogen

  提出了由五倍不饱和脂肪酸二十碳五烯酸（EPA）（微藻油的一种成分）分两步一锅合成苯的方法。通过一系列的烯烃复分解反应和所得1,4-环己二烯的催化脱氢反应，每个EPA底物分子可有效形成两当量的苯。作为唯一的主要副产物，形成了5-辛烯酸和5-癸二酸。在氢气压力下进行脱氢步骤导致形成它们的饱和类似物癸二酸和辛酸，这两种都是合乎需要的产物，同时不妨碍同时进行苯的脱氢步骤。
• Hawkins,E.G.E.; Large,R., Journal of the Chemical Society. Perkin transactions I, 1974, p. 2561 - 2565
  作者：Hawkins,E.G.E.、Large,R.

  DOI：——

  日期：——
• Occlusion of Grubbs' Catalysts in Active Membranes of Polydimethylsiloxane:  Catalysis in Water and New Functional Group Selectivities
  作者：Martin T. Mwangi、M. Brett Runge、Ned B. Bowden

  DOI：10.1021/ja0642212

  日期：2006.11.1

  The Grubbs' first and second generation catalysts were occluded into cross-linked slabs of polydimethylsiloxane with volumes from 1 mm3 to 1 cm3 by swelling the polymer with catalyst and methylene chloride. Methylene chloride was evaporated under vacuum to yield occluded catalysts where their solvent was polydimethylsiloxane. These occluded catalysts were reacted with alkenes dissolved in H2O or H2O/MeOH mixtures that diffused into the polydimethylsiloxane to react by ring-closing metathesis and cross metathesis. Control experiments revealed that the catalysts remained occluded and metathesis did not occur in the solvent. Occlusion of these catalysts allowed commercially available Grubbs' catalysts to be used with H2O as the solvent while isolating the H2O sensitive ruthenium methylidene from exposure to H2O. Functional group selective experiments were carried out where the polydimethylsiloxane was an "active" membrane to exclude salts. Polydimethylsiloxane is a hydrophobic polymer, so the deprotonated salt of diallylmalonic acid did not diffuse into it while a diallylether diffused into it and reacted by metathesis. Thus, by controlling the polarity of reagents their reactivity can be controlled owing to the properties of polydimethylsiloxane rather than those of the Grubbs' catalysts. Occlusion of catalysts in polydimethylsiloxane has been shown to add new selectivities to mature catalysts.