ethyl (4Z,7Z,10Z,13Z,16Z,19Z)-2-hydroxydocosa-4,7,10,13,16,19-hexaenoate | 147544-49-8

• 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: ethyl (4Z,7Z,10Z,13Z,16Z,19Z)-2-hydroxydocosa-4,7,10,13,16,19-hexaenoate
• CAS: 147544-49-8
• 化学式: C₂₄H₃₆O₃
• 分子量: 372.548
• InChiKey: BYQITZFBASLMJC-YNUSHXQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  27
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  ethyl (4Z,7Z,10Z,13Z,16Z,19Z)-2-hydroxydocosa-4,7,10,13,16,19-hexaenoate 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 66.0h， 生成 ethyl (4Z,7Z,10Z,13Z,16Z,19Z)-2-aminodocosa-4,7,10,13,16,19-hexaenoate
  参考文献：
  名称：

  脯氨酸衍生物，其包含衍生自天然和合成脂肪酸的疏水性长链

  摘要：

  α-疏水长链-α-氨基酯是通过一系列脂肪酸酯的α-羟基化制备的[衍生自油酸（OA），亚油酸（LA），花生四烯酸（ARA）和二十二碳六烯酸（DHA）然后进行Mitsunobu反应和邻苯二甲酰亚胺的肼解反应。将这些氨基酯与醛和亲电烯烃混合，可得到非常好的化学收率，并在α位掺入疏水性长链的脯氨酸酯衍生物具有非对映选择性。这种多组分的1,3-偶极环加成反应（1,3-DC）在室温下进行。OA的同源物的疏水性链的合成是通过其氧化执行以醛/外消旋ñ -叔丁基亚亚胺/内夫反应。最终的1,3-DC与苯甲醛和N-甲基马来酰亚胺提供高产率的脯氨酸脯氨酸衍生物。

  DOI：

  10.1016/j.tet.2019.01.051
• 作为产物：
  描述：

  二十二碳六烯酸 在 硫酸 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 32.0h， 生成 ethyl (4Z,7Z,10Z,13Z,16Z,19Z)-2-hydroxydocosa-4,7,10,13,16,19-hexaenoate
  参考文献：
  名称：

  脯氨酸衍生物，其包含衍生自天然和合成脂肪酸的疏水性长链

  摘要：

  α-疏水长链-α-氨基酯是通过一系列脂肪酸酯的α-羟基化制备的[衍生自油酸（OA），亚油酸（LA），花生四烯酸（ARA）和二十二碳六烯酸（DHA）然后进行Mitsunobu反应和邻苯二甲酰亚胺的肼解反应。将这些氨基酯与醛和亲电烯烃混合，可得到非常好的化学收率，并在α位掺入疏水性长链的脯氨酸酯衍生物具有非对映选择性。这种多组分的1,3-偶极环加成反应（1,3-DC）在室温下进行。OA的同源物的疏水性链的合成是通过其氧化执行以醛/外消旋ñ -叔丁基亚亚胺/内夫反应。最终的1,3-DC与苯甲醛和N-甲基马来酰亚胺提供高产率的脯氨酸脯氨酸衍生物。

  DOI：

  10.1016/j.tet.2019.01.051

文献信息

• NEW DHA DERIVATIVES AND THEIR USE AS MEDICAMENTS
  申请人：Pronova BioPharma Norge AS

  公开号：EP1888727B1

  公开（公告）日：2015-04-15
• Novel compounds
  申请人：Bryhn Morten

  公开号：US20070088170A1

  公开（公告）日：2007-04-19

  Compounds of formula (I); wherein R 1 and R 2 are the same or different and may be selected from the group consisting of a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; and X represents a carboxylic acid group, a carboxylate group, or a carboxamide group; or any pharmaceutically acceptable salt, solvate, complex or pro-drug thereof, with the provisos that the compound of formula (I) is not (all-Z)-4,7,10,13,16,19-docosahexaenoic acid (DHA), alpha-methyl DHA, alpha-methyl DHA methyl ester, alpha-methyl DHA ethyl ester or alpha-hydroxy DHA ethyl ester, are disclosed. A fatty acid composition and a pharmaceutical composition comprising such compounds are also disclosed. The use of such compounds as medicaments, in particular for the treatment of diabetes type 2, is also disclosed.
• Novel Compounds
  申请人：Bryhn Morten

  公开号：US20080300306A1

  公开（公告）日：2008-12-04

  Compounds of formula (I); wherein R 1 and R 2 are the same or different and may be selected from the group consisting of a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; and X represents a carboxylic acid group, a carboxylate group, or a carboxamide group; or any pharmaceutically acceptable salt, solvate, complex or pro-drug thereof, with the provisos that the compound of formula (I) is not (all-Z)-4,7,10,13,16,19-docosahexaenoic acid (DHA), alpha-methyl-DHA, alpha-methyl DHA methyl ester, alpha-methyl-DHA ethyl ester or alpha-hydroxy DHA ethyl ester, are disclosed. A fatty acid composition and a pharmaceutical composition comprising such compounds are also disclosed. The use of such compounds as medicaments, in particular for the treatment of diabetes type 2, is also disclosed.
• NOVEL COMPOUNDS
  申请人：Bryhn Morten

  公开号：US20120065260A1

  公开（公告）日：2012-03-15

  Compounds of formula (I); wherein R 1 and R 2 are the same or different and may be selected from the group consisting of a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; and X represents a carboxylic acid group, a carboxylate group, or a carboxamide group; or any pharmaceutically acceptable salt, solvate, complex or pro-drug thereof, with the provisos that the compound of formula (I) is not (all-Z)-4,7,10,13,16,19-docosahexaenoic acid (DHA), alpha-methyl DHA, alpha-methyl DHA methyl ester, alpha-methyl DHA ethyl ester or alpha-hydroxy DHA ethyl ester, are disclosed. A fatty acid composition and a pharmaceutical composition comprising such compounds are also disclosed. The use of such compounds as medicaments, in particular for the treatment of diabetes type 2, is also disclosed.
• US7550613B2
  申请人：——

  公开号：US7550613B2

  公开（公告）日：2009-06-23