(3aR,7S,7aR)-7-ethyl-7-hydroxy-2,2-dimethyl-3a,4,6,7a-tetrahydro-1,3-benzodioxol-5-one | 1187824-43-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,7S,7aR)-7-ethyl-7-hydroxy-2,2-dimethyl-3a,4,6,7a-tetrahydro-1,3-benzodioxol-5-one
• CAS: 1187824-43-6
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: MBRXRZUQWCBZGL-KKZNHRDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,7S,7aR)-7-ethyl-7-hydroxy-2,2-dimethyl-3a,4,6,7a-tetrahydro-1,3-benzodioxol-5-one 在 sodium hydroxide 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 以93%的产率得到(4R,5S)-5-ethyl-4,5-dihydroxycyclohex-2-en-1-one
  参考文献：
  名称：

  Synthesis of the Fully Glycosylated Cyclohexenone Core of Lomaiviticin A

  摘要：

  We describe two four-step sequences for conversion of the inexpensive reagent ethyl sorbate to either O-allyl-N,N-dimethyl-D-pyrrolosamine or O-allyl-L-oleandrose, protected forms of the 2,6-dideoxy sugar residues found in the complex bacterial metabolite lomaiviticin A. We also report a gram-scale synthesis of the highly-oxygenated cyclohexenone ring of this metabolite, and show this may be coupled with the aforementioned donors to form the bis(glycoside) 6. The longest linear sequence to 6 is nine steps.

  DOI：

  10.1021/ol901710b
• 作为产物：
  描述：

  (3aR,4S,6S,7aR)-4-ethyl-6-(hydroxymethyl)-2,2-dimethyl-3a,5,7,7a-tetrahydro-1,3-benzodioxole-4,6-diol 在 sodium periodate 作用下， 反应 0.75h， 以89%的产率得到(3aR,7S,7aR)-7-ethyl-7-hydroxy-2,2-dimethyl-3a,4,6,7a-tetrahydro-1,3-benzodioxol-5-one
  参考文献：
  名称：

  Synthesis of the Fully Glycosylated Cyclohexenone Core of Lomaiviticin A

  摘要：

  We describe two four-step sequences for conversion of the inexpensive reagent ethyl sorbate to either O-allyl-N,N-dimethyl-D-pyrrolosamine or O-allyl-L-oleandrose, protected forms of the 2,6-dideoxy sugar residues found in the complex bacterial metabolite lomaiviticin A. We also report a gram-scale synthesis of the highly-oxygenated cyclohexenone ring of this metabolite, and show this may be coupled with the aforementioned donors to form the bis(glycoside) 6. The longest linear sequence to 6 is nine steps.

  DOI：

  10.1021/ol901710b