5-bromopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate | 196940-78-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-bromopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• CAS: 196940-78-0
• 化学式: C₁₃H₂₄BrNO₃
• 分子量: 322.242
• InChiKey: KOCPTQMPLYFABU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-bromopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (Z)-6-phenyl-hex-5-enyl ester
  参考文献：
  名称：

  Synthesis of Enantiomerically and Diastereomerically Pure Cyclopentanols by asymmetric Cyclocarbolithiation of 5-Alkenyl Carbamates

  摘要：

  DOI：

  10.1002/anie.199717641
• 作为产物：
  描述：

  5-hydroxypentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以97%的产率得到5-bromopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  (−)-Sparteine-Mediated Asymmetric Intramolecular Carbolithiation of Alkenes: Synthesis of Enantiopure Cyclopentanes with Three Consecutive Stereogenic Centers

  摘要：

  An asymmetric intramolecular carbolithiation reaction was developed by combining the (-)-sparteine-mediated enantiotopos-differentiating deprotonation and the anionic 5-exo-trig cyclization. Achiral 6-phenyl-hex-5-enyl carbamates were efficiently cyclized furnishing regio-, diastereo- (dr > 99:1),and enantioselectively (er >98:2) 1,2-trans-substituted cyclopentanes. The intermediate primary benzylic Lithium-carbanion pairs were - in spite of their configurative lability - diastereoselectively substituted by versatile electrophiles creating a third consecutive stereogenic center. Additionally, some 4-functionalized 6-phenylhex-5-enyl carbamates were also cyclized in high yield to provide enantiomericaliy pure cyclopentanes incorporating three adjacent stereogenic centers.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<1860::aid-hlca1860>3.0.co;2-8