N-((2S,3R,4E,6E)-1,3-dihydroxyoctadeca-4,6-dien-2-yl)octanamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: N-((2S,3R,4E,6E)-1,3-dihydroxyoctadeca-4,6-dien-2-yl)octanamide
• 英文别名: (2S,3R)-(4E,6E)-2-octanoylamidooctadecadiene-1,3-diol；(2S,3R)-(4E,6E)-2-octanoylaminooctadecadiene-1,3-diol；N-[(2S,3R,4E,6E)-1,3-dihydroxyoctadeca-4,6-dien-2-yl]octanamide
• 化学式: C₂₆H₄₉NO₃
• 分子量: 423.68
• InChiKey: HICYTBSZMLQZEO-QQPJVBCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  30
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  辛酸 、 (2S,3R,4E,6E)-2-aminooctadeca-4,6-diene-1,3-diol 在 1-羟基苯并三唑 、 1,2-二氯乙烷 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 以81%的产率得到N-((2S,3R,4E,6E)-1,3-dihydroxyoctadeca-4,6-dien-2-yl)octanamide
  参考文献：
  名称：

  从二氢神经酰胺去饱和酶-1向[δ6]不饱和底物的构型偏爱到新抑制剂的发现

  摘要：

  DES1的朝向[资本德尔塔]的构型优选6不饱和的二氢类似物推出一种有效的DES1抑制剂。

  DOI：

  10.1039/c6cc08268h

文献信息

• Synthesis of New Trans Double-Bond Sphingolipid Analogues:  Δ^4,6 and Δ⁶ Ceramides
  作者：Jiong Chun、Guoqing Li、Hoe-Sup Byun、Robert Bittman

  DOI：10.1021/jo0162639

  日期：2002.4.1

  Unsaturation was introduced at Delta(4.6) and Delta(6) of the sphingoid chain of naturally occurring ceramide 1 via a beta-keto sulfoxide (12) and sulfone (18) derived from N-Boe-L-serine methyl ester acetonide (9), affording two novel ceramide analogues, (2S,3R)-2-octanoylamidooetadeca-(4E,6E)-diene-1,3-diol (2) and (2S,3R)-2-octanoylamidooetadec-(6E)-ene-1,3-diol (3). After C-alkylation of 12 with (E)1-bromo-2-tetradecene (8), a trans double bond was installed by elimination of PhS(O)H, providing conjugated dienone oxazolidine 13. Reaction of 18 with 8, followed by desulfonation (AI(Hg)), afforded keto-oxazolidine 20, which bears a (E)-Delta(6) double bond. The syntheses of analogues 2 and 3 from ketones 13 and 20, respectively, were completed by the following sequence of reactions: diastereoselective reduction (NaBH4/CeCl3 or DIBAL-H), hydrolysis of the oxazolidine ring, liberation of the amino group, and installation of the N-amide group.
• From the configurational preference of dihydroceramide desaturase-1 towards Δ⁶-unsaturated substrates to the discovery of a new inhibitor
  作者：Ana Pou、José-Luís Abad、Yadira F. Ordóñez、Maria Garrido、Josefina Casas、Gemma Fabriàs、Antonio Delgado

  DOI：10.1039/c6cc08268h

  日期：——

  The configurational preference of Des1 towards a [capital Delta]6-unsaturated dihydroceramide analog unveils a potent Des1 inhibitor.

  DES1的朝向[资本德尔塔]的构型优选6不饱和的二氢类似物推出一种有效的DES1抑制剂。