(E)-1-bromo-2-tetradecene | 410082-66-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: (E)-1-bromo-2-tetradecene
• 英文别名: (E)-1-bromotetradec-2-ene
• CAS: 410082-66-5
• 化学式: C₁₄H₂₇Br
• 分子量: 275.272
• InChiKey: ARDXTMWOGOWDKF-OUKQBFOZSA-N

物化性质

• 沸点：
  309.8±11.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  15
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-1-bromo-2-tetradecene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 N-tert-butoxycarbonyl (4S)-4-[1'-oxo-2'-phenylsulfonyl-(4'E)-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine
  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
• 作为产物：
  描述：

  十二醛 在 N-溴代丁二酰亚胺(NBS) 、 二异丁基氢化铝 、 三乙胺 、 三苯基膦 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 (E)-1-bromo-2-tetradecene
  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

• Construction of Chemical Libraries of Volatile Compounds by Combinatorial Synthesis of Homologous Mixtures: Alk‐4‐en‐1‐ols, Alk‐4‐enals and Methyl Alk‐4‐enoates
  作者：Coline Perrin、Nicolas Baldovini

  DOI：10.1002/cbdv.202200817

  日期：2023.2

  for their identification in GC/MS analyses. We demonstrate here that compound libraries can be prepared by combinatorial syntheses using long linear synthetic sequences, i. e., eight step in the case of 4-enals. The resulting mixtures of homologues are still perfectly exploitable to deliver the requested information such as clean mass spectra and good gas chromatographic retention indices.

  包含 66 个线性化合物的化合物库，六个分子家族的 11 个代表：( E )- 和 ( Z )-alk-4-en-1-ols、alk-4-enals 和甲基 alk-4-enoates 的异构体, 是通过组合合成制备的, 以允许创建直接可用于在 GC/MS 分析中识别它们的质谱数据库。我们在这里证明化合物库可以通过使用长线性合成序列的组合合成来制备，即。即，在 4-enals 的情况下为八步。由此产生的同系物混合物仍然可以完美地用于提供所需的信息，例如干净的质谱和良好的气相色谱保留指数。
• 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.