tert-butyl (3aR,4R,7aR)-6-formyl-2,2-dimethyl-4-[(2-methylpropan-2-yl)oxycarbonyloxy]-3a,4,5,7a-tetrahydro-1,3-benzoxazole-3-carboxylate | 941303-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tert-butyl (3aR,4R,7aR)-6-formyl-2,2-dimethyl-4-[(2-methylpropan-2-yl)oxycarbonyloxy]-3a,4,5,7a-tetrahydro-1,3-benzoxazole-3-carboxylate
• CAS: 941303-67-9
• 化学式: C₂₀H₃₁NO₇
• 分子量: 397.469
• InChiKey: ORHKWZOZKXPIKD-RBSFLKMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (3aR,4R,7aR)-6-formyl-2,2-dimethyl-4-[(2-methylpropan-2-yl)oxycarbonyloxy]-3a,4,5,7a-tetrahydro-1,3-benzoxazole-3-carboxylate 在 sodium chlorite 、 potassium dihydrogenphosphate 、 2-甲基-2-丁烯 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 生成 (3R,4R,5R)-4-amino-3,5-dihydroxy-cyclohex-1-en-carboxylic acid
  参考文献：
  名称：

  Parallel synthesis of individual shikimic acid-like molecules using a mixture-operation strategy and ring-closing enyne metathesis

  摘要：

  Three new diastereomeric shikimic acid analogues (4-amino-3,5-dihydroxyl-cyclohex-1-en-carboxylic acids, 16) bearing a C-4 amino group were synthesized in parallel by a mixture-operation protocol. Ring-closing enyne metathesis (RCEYM) under ethylene atmosphere was successfully employed to construct the desired carbocycles in high efficiency. The absolute configurations of each final product were confirmed by the ID and 2D NMR techniques. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.118
• 作为产物：
  描述：

  tert-butyl (3aR,4R,7aR)-6-ethenyl-2,2-dimethyl-4-[(2-methylpropan-2-yl)oxycarbonyloxy]-3a,4,5,7a-tetrahydro-1,3-benzoxazole-3-carboxylate 在 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以60%的产率得到tert-butyl (3aR,4R,7aR)-6-formyl-2,2-dimethyl-4-[(2-methylpropan-2-yl)oxycarbonyloxy]-3a,4,5,7a-tetrahydro-1,3-benzoxazole-3-carboxylate
  参考文献：
  名称：

  Parallel synthesis of individual shikimic acid-like molecules using a mixture-operation strategy and ring-closing enyne metathesis

  摘要：

  Three new diastereomeric shikimic acid analogues (4-amino-3,5-dihydroxyl-cyclohex-1-en-carboxylic acids, 16) bearing a C-4 amino group were synthesized in parallel by a mixture-operation protocol. Ring-closing enyne metathesis (RCEYM) under ethylene atmosphere was successfully employed to construct the desired carbocycles in high efficiency. The absolute configurations of each final product were confirmed by the ID and 2D NMR techniques. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.118