(S)-2-Bromomethyl-hexadec-1-en-3-ol | 878999-60-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (S)-2-Bromomethyl-hexadec-1-en-3-ol
• CAS: 878999-60-1
• 化学式: C₁₇H₃₃BrO
• 分子量: 333.352
• InChiKey: XCDNKNONCMZMEC-KRWDZBQOSA-N

物化性质

• 沸点：
  395.1±30.0 °C(Predicted)
• 密度：
  1.057±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.0
• 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：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Bromomethyl-hexadec-1-en-3-ol 在 (H₂IMes)Cl₂Ru(CH-o-OiPrC₆H₄) 咪唑 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 68.0h， 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：

  (S)-2-Methylene-hexadecane-1,3-diol 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以63%的产率得到(S)-2-Bromomethyl-hexadec-1-en-3-ol
  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