vinyl ricinoleate | 49676-79-1

• 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: vinyl ricinoleate
• 英文别名: ethenyl (Z,12R)-12-hydroxyoctadec-9-enoate
• CAS: 49676-79-1
• 化学式: C₂₀H₃₆O₃
• 分子量: 324.504
• InChiKey: UNFJSVVAJDSOJY-KWRJMZDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  vinyl ricinoleate 在 吡啶 、 AK lipase 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Stereodivergent synthesis of both (2S)- and (2R)-1-monoricinolein derivatives by lipase-catalyzed hydrolysis or transesterification directed to new ferroelectric liquid crystals

  摘要：

  The preparation of both (2S)- and (2R)-1-monoricinolein derivatives has been developed to synthesize ferroelectric liquid crystals. Lipase-catalyzed hydrolysis of 2-protected-1,3-diricinoleins provided (2S)-1-monoricinolein derivatives with high diastereoselectivities, while transesterification of 2-protected glycerols with vinyl recinoleate gave (2R)-1-monoricinolein counterparts in good yields with high diastereoselectivities. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.009
• 作为产物：
  描述：

  乙酸乙烯酯 、 蓖麻油酸 在 palladium diacetate 、 氢氧化钾 作用下， 反应 24.0h， 以58%的产率得到vinyl ricinoleate
  参考文献：
  名称：

  Enzymatic esterification of glycerol III. Lipase‐catalyzed synthesis of regioisomerically pure 1,3‐sn‐diacylglycerols and 1 (3)‐rac‐monoacylglycerols derived from unsaturated fatty acids

  摘要：

  摘要 利用具有高区域选择性和广泛底物耐受性的脂肪酶作为催化剂，在不可逆酰基转移条件下对甘油进行高效酯化。油酸、亚油酸、芥酸、蓖麻酸、羟基硬脂酸和科里奥利酸等多种不饱和脂肪酸以乙烯基酯的形式被用于此目的。在对生物催化剂的区域选择性（RE）和底物耐受性进行系统筛选的基础上，选择了合适的生物催化剂。实验发现，这些生物催化剂在特异性、选择性和非特异性方面存在明显差异，并以 RE 数值表示。在这些实验的基础上，以制备规模（150 毫摩尔）合成了多种分子，产率高（约 85%），区域异构纯度高（95% RE）。

  DOI：

  10.1007/bf02523518

文献信息

• MULTI-COMPONENT ETHYLENE COPOLYMERS, PROCESS FOR THEIR PREPARATION, AND VULCANIZATE THEREOF
  申请人：SHOWA DENKO KABUSHIKI KAISHA

  公开号：EP0181408B1

  公开（公告）日：1990-10-24
• US5093429A
  申请人：——

  公开号：US5093429A

  公开（公告）日：1992-03-03
• US5252675A
  申请人：——

  公开号：US5252675A

  公开（公告）日：1993-10-12
• Enzymatic esterification of glycerol III. Lipase‐catalyzed synthesis of regioisomerically pure 1,3‐<i>sn</i>‐diacylglycerols and 1 (3)‐<i>rac</i>‐monoacylglycerols derived from unsaturated fatty acids
  作者：Claudia Waldinger、Manfred Schneider

  DOI：10.1007/bf02523518

  日期：1996.11

  Lipases that display high regioselectivities and broad substrate tolerance were used as catalysts for the efficient esterification of glycerol under the conditions of irreversible acyl transfer. A variety of unsaturated fatty acids, such as oleic, linoleic, erucic, ricinolic, hydroxystearic and coriolic acid, were used for this purpose in the form of their vinyl esters. Suitable biocatalysts were chosen on the basis of systematic screening experiments regarding their regioselectivities (RE) and substrate tolerances. Distinct differences were found and expressed in numerical RE values as a measure for differences of these biocatalysts as being specific, selective, and nonspecific. Based on these experiments, a variety of molecules were synthesized on a preparative scale (>150 mmol) in good yield (ca.85%) and with high regioisomerical purities (>95% RE).

  摘要 利用具有高区域选择性和广泛底物耐受性的脂肪酶作为催化剂，在不可逆酰基转移条件下对甘油进行高效酯化。油酸、亚油酸、芥酸、蓖麻酸、羟基硬脂酸和科里奥利酸等多种不饱和脂肪酸以乙烯基酯的形式被用于此目的。在对生物催化剂的区域选择性（RE）和底物耐受性进行系统筛选的基础上，选择了合适的生物催化剂。实验发现，这些生物催化剂在特异性、选择性和非特异性方面存在明显差异，并以 RE 数值表示。在这些实验的基础上，以制备规模（150 毫摩尔）合成了多种分子，产率高（约 85%），区域异构纯度高（95% RE）。
• Stereodivergent synthesis of both (2S)- and (2R)-1-monoricinolein derivatives by lipase-catalyzed hydrolysis or transesterification directed to new ferroelectric liquid crystals
  作者：Iwao Hachiya、Yoshihumi Sugiura、Hiromasa Araki、Osamu Inaoka、Makoto Shimizu、Masatsugu Akita、Takashi Hamaguchi

  DOI：10.1016/j.tetasy.2007.04.009

  日期：2007.5

  The preparation of both (2S)- and (2R)-1-monoricinolein derivatives has been developed to synthesize ferroelectric liquid crystals. Lipase-catalyzed hydrolysis of 2-protected-1,3-diricinoleins provided (2S)-1-monoricinolein derivatives with high diastereoselectivities, while transesterification of 2-protected glycerols with vinyl recinoleate gave (2R)-1-monoricinolein counterparts in good yields with high diastereoselectivities. (c) 2007 Elsevier Ltd. All rights reserved.