6-bromo-N-((3aS,4R,7aR)-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxol-4-yl)benzo[d][1,3]dioxole-5-carboxamide | 1161437-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-bromo-N-((3aS,4R,7aR)-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxol-4-yl)benzo[d][1,3]dioxole-5-carboxamide
• CAS: 1161437-22-4
• 化学式: C₁₇H₁₈BrNO₅
• 分子量: 396.238
• InChiKey: UBUMVWFDUKEUGG-JMSVASOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.02
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-bromo-N-((3aS,4R,7aR)-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxol-4-yl)benzo[d][1,3]dioxole-5-carboxamide 在 三正丁胺 、 palladium diacetate 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 60.0h， 以48%的产率得到(3aS,3bR,10bS,12aR)-2,2-dimethyl-3b,4,10b,12a-tetrahydrobis[1,3]dioxolo[4,5-c:4',5'-j]phenanthridin-5(3aH)-one
  参考文献：
  名称：

  Desymmetrization of Hydrazinocyclohexadienes: A New Approach for the Synthesis of Polyhydroxylated Aminocyclohexanes

  摘要：

  Hydrazinocyclohexadienes, easily prepared by an ene-reaction between commercially available azodicarboxylate reagents and cyclohexadiene, are interesting substrates for desymmetrization reactions. Under Sharpless asymmetric dihydroxylation conditions, they can lead efficiently to several chiral building blocks as well as advanced precursors of biologically active compounds.

  DOI：

  10.1021/ol900779v
• 作为产物：
  描述：

  6-bromo-N-((1R,5R,6S)-5,6-dihydroxycyclohex-2-enyl)benzo[d][1,3]dioxole-5-carboxamide 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以98%的产率得到6-bromo-N-((3aS,4R,7aR)-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxol-4-yl)benzo[d][1,3]dioxole-5-carboxamide
  参考文献：
  名称：

  Desymmetrization of Hydrazinocyclohexadienes: A New Approach for the Synthesis of Polyhydroxylated Aminocyclohexanes

  摘要：

  Hydrazinocyclohexadienes, easily prepared by an ene-reaction between commercially available azodicarboxylate reagents and cyclohexadiene, are interesting substrates for desymmetrization reactions. Under Sharpless asymmetric dihydroxylation conditions, they can lead efficiently to several chiral building blocks as well as advanced precursors of biologically active compounds.

  DOI：

  10.1021/ol900779v