(2S,3R,4E,6E)-2-aminooctadeca-4,6-diene-1,3-diol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,3R,4E,6E)-2-aminooctadeca-4,6-diene-1,3-diol
• 化学式: C₁₈H₃₅NO₂
• 分子量: 297.481
• InChiKey: BXFSVOSKIKQECX-UUPJVKADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (S)-tert-butyl 4-((R,2E,4E)-1-hydroxyhexadeca-2,4-dien-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 10.0h， 生成 (2S,3R,4E,6E)-2-aminooctadeca-4,6-diene-1,3-diol
  参考文献：
  名称：

  Synthesis of New Trans Double-Bond Sphingolipid Analogues:  Δ^4,6 and Δ⁶ Ceramides

  摘要：

  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.

  DOI：

  10.1021/jo0162639

文献信息

• USE OF UNSATURATED SPHINGOSINE COMPOUNDS AS CHEMOTHERAPEUTIC AGENTS FOR THE TREATMENT OF CANCER
  申请人：Saba Julie D.

  公开号：US20110098317A1

  公开（公告）日：2011-04-28

  The present invention is directed to unsaturated sphingosine compounds which are useful as therapeutic agents for the treatment of cancer and for the treatment of other diseases including diabetes and infection with intracellular bacteria. This invention is also directed to methods of using the compounds and pharmaceutical compositions comprising the compounds in treating these diseases.
• US8741967B2
  申请人：——

  公开号：US8741967B2

  公开（公告）日：2014-06-03
• US9133097B2
  申请人：——

  公开号：US9133097B2

  公开（公告）日：2015-09-15
• 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。
• 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.