Octadeca-6,9,12-triene

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: Octadeca-6,9,12-triene
• 化学式: C₁₈H₃₂
• 分子量: 248.452
• InChiKey: DTIVBBCEMQZIEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  甲醇 、 (Z,Z)-9,12-十八烷二烯酸二聚物 在 [1,3-bis(2,4,5-Me₃Ph)-2-imidazolidinylidene]Ru=CHPh(PCy₃)Cl₂ 、 硫酸 作用下， 反应 48.5h， 生成 Octadeca-6,9,12-triene 、 (9E,12E,15E)-Tetracosa-9,12,15-trienedioic acid dimethyl ester 、 5-dodecene 、 二甲基十八碳-9-烯二酸酯
  参考文献：
  名称：

  不饱和脂肪酸的复分解：长链不饱和α，ω-二羧酸的合成

  摘要：

  AbstractThe self‐metathesis of readily available monounsaturated FA has the potential of being an important pathway for the synthesis of symmetrical long‐chain unsaturated‐α,ω‐dicarboxylic acids (C18−C26). Previous studies on the self‐metathesis of monounsaturated FA esters using ruthenium catalysts in solution, however, suffered from low conversions as a result of the thermodynamic control of the reaction. We have found that the second‐generation Grubbs catalyst can effectively catalyze the solvent‐free self‐metathesis of monounsaturated FA of varying purity (from 90 to 99%) to afford two important products—monounsaturated dicarboxylic acids and hydrocarbons—in very high molar conversions (>80%). This solvent‐free self‐metathesis reaction also works for monounsaturated FA containing additional functional groups. Reactions were conducted at catalyst loadings as low as 0.005 mol%, and turnover numbers as high as 10,800 could be obtained. This discovery represents an attractive approach to the large‐scale production of useful monounsaturated‐α,ω‐dicarboxylic acids and long‐chain unsaturated hydrocarbons by means of this solvent‐free ruthenium‐catalyzed self‐metathesis of readily available monounsaturated FA.

  DOI：

  10.1007/s11746-006-1249-0

文献信息

• Method of producing dicarboxylic acids
  申请人：The United States of America as represented by the Secretary of Agriculture

  公开号：US07534917B1

  公开（公告）日：2009-05-19

  A method of producing dicarboxylic acids (e.g., α,ω dicarboxylic acids) by reacting a compound having a terminal COOH (e.g., unsaturated fatty acid such as oleic acid) and containing at least one carbon-carbon double bond with a second generation Grubbs catalyst in the absence of solvent to produce dicarboxylic acids. The method is conducted in an inert atmosphere (e.g., argon, nitrogen). The process also works well with mixed unsaturated fatty acids obtained from soybean, rapeseed, tall, and linseed oils.

  一种生产二羧酸（例如，α,ω-二羧酸）的方法，通过将具有末端COOH的化合物（例如，不饱和脂肪酸如油酸）与至少含有一个碳-碳双键的第二代Grubbs催化剂在无溶剂的情况下反应，以产生二羧酸。该方法在惰性气氛（例如，氩气、氮气）中进行。此过程也适用于从大豆、油菜籽、海藻和亚麻籽油中获得的混合不饱和脂肪酸。