(S)-2-Methylene-hexadecane-1,3-diol | 878999-37-2

• 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: (S)-2-Methylene-hexadecane-1,3-diol
• 英文别名: (3S)-2-methylidenehexadecane-1,3-diol
• CAS: 878999-37-2
• 化学式: C₁₇H₃₄O₂
• 分子量: 270.456
• InChiKey: AUUQAPQAAUEDDB-KRWDZBQOSA-N

物化性质

• 熔点：
  53-55 °C
• 沸点：
  397.5±22.0 °C(Predicted)
• 密度：
  0.903±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Methylene-hexadecane-1,3-diol 在 (H₂IMes)Cl₂Ru(CH-o-OiPrC₆H₄) 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 (S)-4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-tetradecyl]-2-methyl-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis of 1-Deoxysphingosine Derivatives with Conformationally Restricted Pyrrolidinediol Head Groups

  摘要：

  A family of cyclic 1-deoxysphingolipid derivatives of structure 4 has been designed and synthesized, which may serve as tumorigenesis suppressors for various cancers. Compound 4 is a second-generation analogue developed from sphingosine (1), in which a hydroxyl substituent is moved from C1 to C5 and a methylene is added for conformational rigidity between the C2-nitrogen substituent and C4. The synthetic chemistry for pyrrolidine ring closure at C3-C4 features ring-closing metathesis followed by hydroboration-oxidation.

  DOI：

  10.1021/ol052839v
• 作为产物：
  描述：

  ((2S,3S)-2-Methyl-3-tridecyl-oxiranyl)-methanol 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.0h， 以88%的产率得到(S)-2-Methylene-hexadecane-1,3-diol
  参考文献：
  名称：

  Synthesis of 1-Deoxysphingosine Derivatives with Conformationally Restricted Pyrrolidinediol Head Groups

  摘要：

  A family of cyclic 1-deoxysphingolipid derivatives of structure 4 has been designed and synthesized, which may serve as tumorigenesis suppressors for various cancers. Compound 4 is a second-generation analogue developed from sphingosine (1), in which a hydroxyl substituent is moved from C1 to C5 and a methylene is added for conformational rigidity between the C2-nitrogen substituent and C4. The synthetic chemistry for pyrrolidine ring closure at C3-C4 features ring-closing metathesis followed by hydroboration-oxidation.

  DOI：

  10.1021/ol052839v