(1R)-1-(3-butenyl)-2-undecynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate | 397300-89-9

• 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: (1R)-1-(3-butenyl)-2-undecynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• 英文别名: [(5R)-pentadec-1-en-6-yn-5-yl] 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• CAS: 397300-89-9
• 化学式: C₂₃H₃₉NO₃
• 分子量: 377.568
• InChiKey: DGJVCYFXUSQLGT-HXUWFJFHSA-N

物化性质

• 沸点：
  455.5±45.0 °C(Predicted)
• 密度：
  0.955±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R)-1-(3-butenyl)-2-undecynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 在 甲烷磺酸 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 23.67h， 生成 (R)-(-)-5-(dec-1-ynyl)-tetrahydrofuran-2-one
  参考文献：
  名称：

  The Preparation of Nonracemic Secondary α-(Carbamoyloxy)alkylzinc and Copper Reagents. A Versatile Approach to Enantioenriched Alcohols

  摘要：

  GRAPHICSChiral alpha-(carbamoyloxy)alkyllithium reagents, prepared using Hoppe's sBuLi/(-)-sparteine methodology, were transmetalated with ZnCl2. Further transmetalation with CuCN with overall retention of configuration gave chiral species that reacted with various electrophiles to give enantiomerically pure alcohols after deprotection. A short, highly efficient synthesis of an industrially relevant pheromone, japonilure, illustrates the value of the methodology.

  DOI：

  10.1021/ol016986e
• 作为产物：
  描述：

  2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl chloride 在 仲丁基锂 、 sodium hydride 、 zinc(II) chloride 、 鹰爪豆碱 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 73.08h， 生成 (1R)-1-(3-butenyl)-2-undecynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  The Preparation of Nonracemic Secondary α-(Carbamoyloxy)alkylzinc and Copper Reagents. A Versatile Approach to Enantioenriched Alcohols

  摘要：

  GRAPHICSChiral alpha-(carbamoyloxy)alkyllithium reagents, prepared using Hoppe's sBuLi/(-)-sparteine methodology, were transmetalated with ZnCl2. Further transmetalation with CuCN with overall retention of configuration gave chiral species that reacted with various electrophiles to give enantiomerically pure alcohols after deprotection. A short, highly efficient synthesis of an industrially relevant pheromone, japonilure, illustrates the value of the methodology.

  DOI：

  10.1021/ol016986e

文献信息

• The Preparation of Nonracemic Secondary α-(Carbamoyloxy)alkylzinc and Copper Reagents. A Versatile Approach to Enantioenriched Alcohols
  作者：Julien P. N. Papillon、Richard J. K. Taylor

  DOI：10.1021/ol016986e

  日期：2002.1.1

  GRAPHICSChiral alpha-(carbamoyloxy)alkyllithium reagents, prepared using Hoppe's sBuLi/(-)-sparteine methodology, were transmetalated with ZnCl2. Further transmetalation with CuCN with overall retention of configuration gave chiral species that reacted with various electrophiles to give enantiomerically pure alcohols after deprotection. A short, highly efficient synthesis of an industrially relevant pheromone, japonilure, illustrates the value of the methodology.