[(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (1S,6R)-1-cyano-3,4-dimethyl-6-phenylcyclohex-3-ene-1-carboxylate | 144901-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (1S,6R)-1-cyano-3,4-dimethyl-6-phenylcyclohex-3-ene-1-carboxylate
• CAS: 144901-86-0
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: AMYQFRKVQITRIA-KGVIQGDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  D-(-)-泛酰内酯 在 4-二甲氨基吡啶 、 四氯化钛 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 45.0h， 生成 [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (1S,6R)-1-cyano-3,4-dimethyl-6-phenylcyclohex-3-ene-1-carboxylate
  参考文献：
  名称：

  Reaction of 2,3-dimethyl-1,3-butadiene with chiral (E)-2-cyanocinnamates.

  摘要：

  The reactions of 2,3-dimethyl-1,3-butadiene with (E)-2-cyanocinnamates of (S)-ethyl lactate (1a) and (R)-pantolactone (1b), catalysed by TiCl4, afford enantiomerically pure cycloadducts which are easily converted into the enantiomers (1R, 6S) and (1S, 6R) of the methyl 1-cyano-3,4-dimethyl-6-phenyl-3-cyclohexen-1-carboxylate. The reactions with TiCl4 can be explained by the dienophile-TiCl4 chelate model proposed by Helmchen. The non-catalysed reaction of (1b) with the same diene takes place at 100-degrees-C, with a moderately high d.e. and reversal of selectivity.

  DOI：

  10.1016/s0957-4166(00)82189-8

文献信息

• Reaction of 2,3-dimethyl-1,3-butadiene with chiral (E)-2-cyanocinnamates.
  作者：A. Avenoza、C. Cativiela、J.A. Mayoral、J.M. Peregrina

  DOI：10.1016/s0957-4166(00)82189-8

  日期：1992.7

  The reactions of 2,3-dimethyl-1,3-butadiene with (E)-2-cyanocinnamates of (S)-ethyl lactate (1a) and (R)-pantolactone (1b), catalysed by TiCl4, afford enantiomerically pure cycloadducts which are easily converted into the enantiomers (1R, 6S) and (1S, 6R) of the methyl 1-cyano-3,4-dimethyl-6-phenyl-3-cyclohexen-1-carboxylate. The reactions with TiCl4 can be explained by the dienophile-TiCl4 chelate model proposed by Helmchen. The non-catalysed reaction of (1b) with the same diene takes place at 100-degrees-C, with a moderately high d.e. and reversal of selectivity.