tert-butyl 1,1-dimethyl (2R,3R)-3-<(1R,4R)-bornylideneamino>-2-<(E)-2-methoxyvinyl>-1,1,3-propanetricarboxylate | 133445-91-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tert-butyl 1,1-dimethyl (2R,3R)-3-<(1R,4R)-bornylideneamino>-2-<(E)-2-methoxyvinyl>-1,1,3-propanetricarboxylate
• 英文别名: 3-O-tert-butyl 1-O,1-O-dimethyl (2R,3R)-2-[(E)-2-methoxyethenyl]-3-[[(1R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanylidene]amino]propane-1,1,3-tricarboxylate
• CAS: 133445-91-7
• 化学式: C₂₅H₃₉NO₇
• 分子量: 465.587
• InChiKey: GZHXGYMAQMXJRA-PRXGKAEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  100.49
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 1,1-dimethyl (2R,3R)-3-<(1R,4R)-bornylideneamino>-2-<(E)-2-methoxyvinyl>-1,1,3-propanetricarboxylate 在 羟胺 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以77%的产率得到2-tert-butyl methyl (2R,3R,4R)-3-<(E)-2-methoxyvinyl>-5-oxopyrrolidine-2,4-dicarboxylate
  参考文献：
  名称：

  Highly diastereoselective Michael addition of lithiated camphor imines of glycine esters to .alpha.,.beta.-unsaturated esters. Synthesis of optically pure 5-oxo-2,4-pyrrolidinedicarboxylates of unnatural stereochemistry

  摘要：

  The lithium enolates of camphor imines of glycine esters underwent highly diastereoselective Michael additions to alpha,beta-unsaturated esters. The tightly chelated structure of the Z,E enolates and the selective approach of the alpha,beta-unsaturated esters to the re face of the enolates were responsible for the high diastereoselectivity observed. The use of alkylidenemalonate acceptors led to the diastereospecific formation of Michael adducts. Removal of the camphor auxiliary of the adducts and concomitant cyclization led to optically pure enantiomeric 5-oxo-2,4-pyrrolidinedicarboxylates of unnatural stereochemistry.

  DOI：

  10.1021/jo00008a052
• 作为产物：
  描述：

  dimethyl [(2E)-3-methoxyprop-2-en-1-ylidene] malonate 、 tert-butyl ((1R,4R)-bornylideneamino)acetate 在 正丁基锂 、 叔丁醇 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以60%的产率得到tert-butyl 1,1-dimethyl (2R,3R)-3-<(1R,4R)-bornylideneamino>-2-<(E)-2-methoxyvinyl>-1,1,3-propanetricarboxylate
  参考文献：
  名称：

  Highly diastereoselective Michael addition of lithiated camphor imines of glycine esters to .alpha.,.beta.-unsaturated esters. Synthesis of optically pure 5-oxo-2,4-pyrrolidinedicarboxylates of unnatural stereochemistry

  摘要：

  The lithium enolates of camphor imines of glycine esters underwent highly diastereoselective Michael additions to alpha,beta-unsaturated esters. The tightly chelated structure of the Z,E enolates and the selective approach of the alpha,beta-unsaturated esters to the re face of the enolates were responsible for the high diastereoselectivity observed. The use of alkylidenemalonate acceptors led to the diastereospecific formation of Michael adducts. Removal of the camphor auxiliary of the adducts and concomitant cyclization led to optically pure enantiomeric 5-oxo-2,4-pyrrolidinedicarboxylates of unnatural stereochemistry.

  DOI：

  10.1021/jo00008a052