(1R,2S,3R)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>-2-spiro<4'<2'-phenyl-5'(4'H)-oxazolone>>-1-trimethylsilyloxy-5-cyclohexene | 174506-59-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2S,3R)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>-2-spiro<4'<2'-phenyl-5'(4'H)-oxazolone>>-1-trimethylsilyloxy-5-cyclohexene
• 英文别名: (5R,6R,10R)-10-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenyl-6-trimethylsilyloxy-3-oxa-1-azaspiro[4.5]deca-1,7-dien-4-one
• CAS: 174506-59-3
• 化学式: C₂₂H₂₉NO₅Si
• 分子量: 415.561
• InChiKey: GKINRXQTGOOHCU-KCXPTXFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>-2-spiro<4'<2'-phenyl-5'(4'H)-oxazolone>>-1-trimethylsilyloxy-5-cyclohexene 在 柠檬酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以90%的产率得到(1R,2S,3R)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>-2-spiro<4'<2'-phenyl-5'(4'H)-oxazolone>>-5-cyclohexen-1-ol
  参考文献：
  名称：

  High-pressure and thermally induced asymmetric diels-alder cycloadditions of heterosubstituted dienes to homochiral α,β-didehydro amino acid derivatives

  摘要：

  An amino pentenoate and an unsaturated oxazolone have shown to be suitable homochiral dienophiles to be reacted with electron-rich heterosubstituted dienes. High-pressure and thermal activation have been studied for these cycloadditions. The adducts obtained are polyfunctional building blocks useful for the synthesis of enantiopure cyclohexane amino acids and related products.

  DOI：

  10.1016/0957-4166(95)00429-7
• 作为产物：
  描述：

  1-(trimethylsiloxy)-1,3-butadiene 、 Z-2-phenyl-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen>-5(4H)-oxazolone 以 二氯甲烷 为溶剂， 反应 6.0h， 以91%的产率得到(1R,2S,3R)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>-2-spiro<4'<2'-phenyl-5'(4'H)-oxazolone>>-1-trimethylsilyloxy-5-cyclohexene
  参考文献：
  名称：

  High-pressure and thermally induced asymmetric diels-alder cycloadditions of heterosubstituted dienes to homochiral α,β-didehydro amino acid derivatives

  摘要：

  An amino pentenoate and an unsaturated oxazolone have shown to be suitable homochiral dienophiles to be reacted with electron-rich heterosubstituted dienes. High-pressure and thermal activation have been studied for these cycloadditions. The adducts obtained are polyfunctional building blocks useful for the synthesis of enantiopure cyclohexane amino acids and related products.

  DOI：

  10.1016/0957-4166(95)00429-7

文献信息

• High-pressure and thermally induced asymmetric diels-alder cycloadditions of heterosubstituted dienes to homochiral α,β-didehydro amino acid derivatives
  作者：Rosa M. Ortuño、Javier Ibarzo、Jean d'Angelo、Françoise Dumas、Angel Alvarez-Larena、Joan F. Piniella

  DOI：10.1016/0957-4166(95)00429-7

  日期：1996.1

  An amino pentenoate and an unsaturated oxazolone have shown to be suitable homochiral dienophiles to be reacted with electron-rich heterosubstituted dienes. High-pressure and thermal activation have been studied for these cycloadditions. The adducts obtained are polyfunctional building blocks useful for the synthesis of enantiopure cyclohexane amino acids and related products.