isopropyl 13-hydroxy-10-oxooctadec-11-enoate | 197149-68-1

• 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: isopropyl 13-hydroxy-10-oxooctadec-11-enoate
• 英文别名: propan-2-yl (E)-13-hydroxy-10-oxooctadec-11-enoate
• CAS: 197149-68-1
• 化学式: C₂₁H₃₈O₄
• 分子量: 354.53
• InChiKey: FEGMCWDTGRCARH-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isopropyl 13-hydroxy-10-oxooctadec-11-enoate 在 Lipase PS 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以82%的产率得到(+/-)-13-hydroxy-10-oxo-trans-11-octadecenoic acid
  参考文献：
  名称：

  Convenient Formation of 4-Hydroxyalk-2-en-1-one Functionality via A Knoevenagel-type Carbon Chain Elongation Reaction of Aldehyde with 1-Arylsulfinylalkan-2-one

  摘要：

  A highly functionalized four-carbon unit, 4-hydroxyalk-2-en-1-one functionality [(RCH)-C-2(OH)CH=CHCOR1], was conveniently prepared by a reaction of an aldehyde ((RCH2CHO)-C-2) with a 1-(arylsulfinyl)alkan-2-one [ArS(O)CH2COR1] in the presence of diethylamine (Knoevenagel condition). Other functional groups, such as carbonyl and hydroxy groups, in both of the alkyl chains (R-1, R-2) did not prevent this reaction. This reaction was used to conveniently prepare (+/-)-(11E)-13-hydroxy-10-oxooctadec-11-enoic acid (14), having cytotoxic activity, and its analogues from undec-10-enoic acid in good yield.

  DOI：

  10.1021/jo001323g
• 作为产物：
  描述：

  isopropyl 10,11-epoxyundecanoate 在 草酰氯 、 potassium carbonate 、 溶剂黄146 、 二甲基亚砜 、 二乙胺 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 6.0h， 生成 isopropyl 13-hydroxy-10-oxooctadec-11-enoate
  参考文献：
  名称：

  Convenient synthesis of cytotoxic (11E)-13-hydroxy-10-oxooctadec-11-enoic acid from undec-10-enoic acid

  摘要：

  (11E)-13-羟基-10-氧代十八-11-烯酸 1 通过 11-苯基亚磺酰基-10-氧代十一烷酸异丙酯 2a（本身很容易衍生自十一-10-烯酸）与庚醛的 Knoevenagel 型反应方便地合成形成γ-羟基烯酮官能团以及碳链伸长。

  DOI：

  10.1039/a706245a

文献信息

• Convenient synthesis of cytotoxic (11E)-13-hydroxy-10-oxooctadec-11-enoic acid from undec-10-enoic acid
  作者：Junzo Nokami、Masahiro Osafune、Kazuhiro Shiraishi、Shin-ichi Sumida、Nobuyuki Imai

  DOI：10.1039/a706245a

  日期：——

  (11E)-13-Hydroxy-10-oxooctadec-11-enoic acid 1 is conveniently synthesized via a Knoevenagel-type reaction of isopropyl 11-phenylsulfinyl-10-oxoundecanoate 2a (itself easily derived from undec-10-enoic acid) with heptanal to form the γ-hydroxyenone functionality together with carbon chain elongation.

  (11E)-13-羟基-10-氧代十八-11-烯酸 1 通过 11-苯基亚磺酰基-10-氧代十一烷酸异丙酯 2a（本身很容易衍生自十一-10-烯酸）与庚醛的 Knoevenagel 型反应方便地合成形成γ-羟基烯酮官能团以及碳链伸长。
• Convenient Formation of 4-Hydroxyalk-2-en-1-one Functionality via A Knoevenagel-type Carbon Chain Elongation Reaction of Aldehyde with 1-Arylsulfinylalkan-2-one
  作者：Junzo Nokami、Kazuhide Kataoka、Kazuhiro Shiraishi、Masahiro Osafune、Iqbal Hussain、Shin-ichi Sumida

  DOI：10.1021/jo001323g

  日期：2001.2.1

  A highly functionalized four-carbon unit, 4-hydroxyalk-2-en-1-one functionality [(RCH)-C-2(OH)CH=CHCOR1], was conveniently prepared by a reaction of an aldehyde ((RCH2CHO)-C-2) with a 1-(arylsulfinyl)alkan-2-one [ArS(O)CH2COR1] in the presence of diethylamine (Knoevenagel condition). Other functional groups, such as carbonyl and hydroxy groups, in both of the alkyl chains (R-1, R-2) did not prevent this reaction. This reaction was used to conveniently prepare (+/-)-(11E)-13-hydroxy-10-oxooctadec-11-enoic acid (14), having cytotoxic activity, and its analogues from undec-10-enoic acid in good yield.