(3aS,7aR)-ethyl 7-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate | 1202183-71-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,7aR)-ethyl 7-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate
• CAS: 1202183-71-8
• 化学式: C₁₂H₁₈O₅
• 分子量: 242.272
• InChiKey: YDMLLAZCHMXIOO-CBMCFHRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3aS,7aR)-ethyl 7-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate 、 4-硝基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到(3aS,7aR)-ethyl 2,2-dimethyl-7-(4-nitrobenzoyloxy)-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate
  参考文献：
  名称：

  A concise route to (−)-shikimic acid and (−)-5-epi-shikimic acid, and their enantiomers via Barbier reaction and ring-closing metathesis

  摘要：

  A simple route for the synthesis of naturally occurring (-)-shikimic acid, (-)-5-epi-shikimic acid, and their enantiomers from D-ribose-derived enantiomeric aldehydes 8a and 8b by employing Barbier reaction and ring-closing metathesis as key steps has been developed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.111
• 作为产物：
  描述：

  ethyl 4-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-4-hydroxy-2-ethylenebutanoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以72%的产率得到(3aS,7aR)-ethyl 7-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate
  参考文献：
  名称：

  A concise route to (−)-shikimic acid and (−)-5-epi-shikimic acid, and their enantiomers via Barbier reaction and ring-closing metathesis

  摘要：

  A simple route for the synthesis of naturally occurring (-)-shikimic acid, (-)-5-epi-shikimic acid, and their enantiomers from D-ribose-derived enantiomeric aldehydes 8a and 8b by employing Barbier reaction and ring-closing metathesis as key steps has been developed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.111