Octadeca-3,6,9,12,15-pentaen-1-ol

• 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: Octadeca-3,6,9,12,15-pentaen-1-ol
• 英文别名: octadeca-3,6,9,12,15-pentaen-1-ol
• 化学式: C₁₈H₂₈O
• 分子量: 260.4
• InChiKey: SRXRRKRCCNIEGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

文献信息

• [EN] PROCESS FOR THE PREPARATION OF A POLYUNSATURATED KETONE COMPOUND<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN COMPOSÉ CÉTONE POLYINSATURÉ
  申请人：AVEXXIN AS

  公开号：WO2016116634A1

  公开（公告）日：2016-07-28

  A process for the preparation of a polyunsaturated thiol comprising: (1) reacting a polyunsaturated alcohol in the presence of a compound of formula R2-SO2Hal wherein R2 is a C1-20 hydrocarbyl group, such an C1-10 alkyl group, to form a polyunsaturated sulphonyl ester; (2) converting the polyunsaturated sulphonyl ester to a polyunsaturated thioester by reacting with an anion of formula -SC(=O)R4 wherein R4 is a C1-20 hydrocarbyl group; (3) converting the polyunsaturated thioester to form a polyunsaturated thiol optionally in the presence of an antioxidant, e.g. using a metal carbonate. (4) reacting said polyunsaturated thiol with a compound (LG)R3COX wherein X is an electron withdrawing group and R3 is an alkylene group carrying a leaving group (LG), such as LG-CH2- forming (I) where X is an electron withdrawing group and LG is a leaving group; optionally in the presence of an antioxidant, so as to form a polyunsaturated ketone compound.

  制备多不饱和硫醇的方法包括：（1）在式R2-SO2Hal的化合物存在下，将多不饱和醇与R2为C1-20烃基的化合物（如C1-10烷基）反应，形成多不饱和磺酰酯；（2）通过与式为-SC(=O)R4的阴离子反应，将多不饱和磺酰酯转化为多不饱和硫酯；（3）在抗氧化剂的存在下，将多不饱和硫酯转化为多不饱和硫醇，例如使用金属碳酸盐；（4）将所述多不饱和硫醇与化合物(LG)R3COX反应，其中X是一个电子吸引基团，R3是携带一个离去基团（LG）的烷基链，如LG-CH2-，形成(I)，其中X是一个电子吸引基团，LG是一个离去基团；在抗氧化剂的存在下，形成多不饱和酮化合物。
• Process for the Synthesis of Long-Chain Fatty Acids
  申请人：Fauq Abdul H.

  公开号：US20110105781A1

  公开（公告）日：2011-05-05

  This invention relates to processes for preparing long-chain fatty acids of Formula I: and salts thereof, as well as intermediates for the processes, wherein L 1 and L 2 are described herein.

  本发明涉及制备式I的长链脂肪酸及其盐的方法，以及用于该方法的中间体，其中L1和L2如本文所述。
• POLYUNSATURATED FATTY ACIDS FOR THE TREATMENT OF DISEASES RELATED TO CARDIOVASCULAR, METABOLIC AND INFLAMMATORY DISEASE AREAS
  申请人：Hovland Ragnar

  公开号：US20120122940A1

  公开（公告）日：2012-05-17

  The present disclosure relates to lipid compounds of the general formula (I): R1-O—C(R2)(R3)-X  (I) wherein R 1 is a C 10 -C 22 alkyl group, a C 10 -C 22 alkenyl group having 1-6 double bonds, or a C 10 -C 22 alkynyl group having 1-6 triple bonds; R 2 and R 3 are the same or different and may be chosen from different substituents; and X is a carboxylic acid or a derivative thereof, such as a carboxylic ester, a carboxylic anhydride, a phospholipid, triglyceride, or a carboxamide; or a pharmaceutically acceptable salt, solvate, solvate of such salt or a prodrug thereof. The present disclosure also relates to pharmaceutical compositions and lipid compositions comprising at least one compound according to the present disclosure, and to such compounds for use as medicaments or for use in therapy, in particular for the treatment of diseases related to the cardiovascular, metabolic, and inflammatory disease area.

  本公开涉及一般式（I）的脂质化合物：R1-O-C（R2）（R3）-X（I），其中R1是C10-C22烷基，具有1-6个双键的C10-C22烯基，或具有1-6个三键的C10-C22炔基；R2和R3相同或不同，可以选择不同的取代基；X是羧酸或其衍生物，例如羧酸酯，羧酸酐，磷脂，甘油三酯或羧酰胺；或药学上可接受的盐，溶剂，该盐的溶剂或其前药。本公开还涉及包含至少一种根据本公开的化合物的制药组合物和脂质组合物，并涉及这些化合物的用途作为药物或用于治疗，特别是用于治疗与心血管，代谢和炎症相关的疾病领域。
• PROCESS FOR THE PREPARATION OF A POLYUNSATURATED KETONE COMPOUND
  申请人：AVEXXIN AS

  公开号：US20160159737A1

  公开（公告）日：2016-06-09

  The invention relates to the manufacture of certain polyunsaturated compounds employing a particular application of the Mitsonobu reaction in the presence of at least one anti-oxidant. We have found a method of making a pharmaceutically-acceptable polyunsaturated ester or thioester compound directly, which can ultimately be converted to the advantageous ketone compounds, in which unwanted oxidation and cis/trans isomerization are substantially reduced or eliminated using particular Mitsonobu chemistry.

  本发明涉及利用Mitsonobu反应的特定应用来制造某些多不饱和化合物，其中至少存在一种抗氧化剂。我们发现了一种直接制造药用多不饱和酯或硫酯化合物的方法，最终可以转化为有利的酮化合物，其中使用特定的Mitsonobu化学方法，可以大大减少或消除不必要的氧化和顺反异构化。
• Process for the preparation of a polyunsaturated ketone compound
  申请人：Avexxin AS

  公开号：US10093618B2

  公开（公告）日：2018-10-09

  The invention relates to the manufacture of certain polyunsaturated compounds employing a particular application of the Mitsonobu reaction in the presence of at least one anti-oxidant. We have found a method of making a pharmaceutically-acceptable polyunsaturated ester or thioester compound directly, which can ultimately be converted to the advantageous ketone compounds, in which unwanted oxidation and cis/trans isomerization are substantially reduced or eliminated using particular Mitsonobu chemistry.

  本发明涉及在至少一种抗氧化剂存在的情况下，采用特定的 Mitsonobu 反应制造某些多不饱和化合物。我们发现了一种直接制造药学上可接受的多不饱和酯或硫酯化合物的方法，这种化合物最终可转化为有利的酮化合物，在这种方法中，利用特殊的 Mitsonobu 化学反应可大大减少或消除不需要的氧化和顺式/反式异构化。