(3aS,4S,5R,7aS)-5-chloro-6-iodo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-yl acetate | 1227264-34-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4S,5R,7aS)-5-chloro-6-iodo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-yl acetate
• 英文别名: [(3aS,4S,5R,7aS)-5-chloro-6-iodo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-yl] acetate
• CAS: 1227264-34-7
• 化学式: C₁₁H₁₄ClIO₄
• 分子量: 372.587
• InChiKey: ZHBVWTDDZXXNBR-AATLWQCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aS,4S,5R,7aS)-5-chloro-6-iodo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-yl acetate 在 sodium methylate 作用下， 以 乙醚 为溶剂， 反应 12.25h， 以76%的产率得到(3aS,5aS,6aS,6bS)-5-iodo-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[e][1,3]benzodioxole
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Carbasugars (+)-Pericosines A−C from Diverse Aromatic cis-Dihydrodiol Precursors

  摘要：

  cis-Dihydrocatechols, derived from biological cis-dihydroxylation of methyl benzoate, iodobenzene and benzonitrile, using the microorganism Pseudomonas putida UV4, were converted into pericosines A, C, and B, respectively. This approach constitutes the shortest syntheses, to date, of these important natural products with densely packed functionalities.

  DOI：

  10.1021/ol100525r
• 作为产物：
  描述：

  (3aR,4R,5S,7aS)-6-iodo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol 、 2-乙酰氧基异丁酰氯 以 乙腈 为溶剂， 以95%的产率得到(3aS,4S,5R,7aS)-5-chloro-6-iodo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-yl acetate
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Carbasugars (+)-Pericosines A−C from Diverse Aromatic cis-Dihydrodiol Precursors

  摘要：

  cis-Dihydrocatechols, derived from biological cis-dihydroxylation of methyl benzoate, iodobenzene and benzonitrile, using the microorganism Pseudomonas putida UV4, were converted into pericosines A, C, and B, respectively. This approach constitutes the shortest syntheses, to date, of these important natural products with densely packed functionalities.

  DOI：

  10.1021/ol100525r