(1R,2R,6S,7S,10S)-10-Hydroxy-7-iodo-3,9-dioxa-tricyclo[5.2.1.0^2,6]decane-4,8-dione | 157729-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,2R,6S,7S,10S)-10-Hydroxy-7-iodo-3,9-dioxa-tricyclo[5.2.1.0^2,6]decane-4,8-dione
• CAS: 157729-80-1
• 化学式: C₈H₇IO₅
• 分子量: 310.045
• InChiKey: DJBVKXPKDJPEIG-JSSSEQFXSA-N

物化性质

• 沸点：
  352.7±42.0 °C(predicted)
• 密度：
  2.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.61
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,6S,7S,10S)-10-Hydroxy-7-iodo-3,9-dioxa-tricyclo[5.2.1.0^2,6]decane-4,8-dione 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以67%的产率得到(1R,2R,6R,7R,10R)-10-Hydroxy-3,9-dioxa-tricyclo[5.2.1.0^2,6]decane-4,8-dione
  参考文献：
  名称：

  Formation of highly substituted cyclopentanes from radical and anionic Michael cyclisations of α-iodo-γ- and -δ-lactones

  摘要：

  alpha-Iodos-delta- and -gamma-hexonolactones with alpha,beta-unsaturated esters developed from C-6 undergo both tributyltin hydride-induced radical and base catalysed anionic Michael cyclisations to form bicyclic lactones with very highly substituted homochiral cyclopentanes. The delta-lactones give cyclopentane products in which adjacent carbon substituents on the cyclopentane ring are cis to each other, whereas gamma-lactones give cyclopentanes in which the carbon chains are trans.

  DOI：

  10.1016/s0040-4039(00)76978-4
• 作为产物：
  描述：

  (3aS,4S,7R,7aS)-7-iodo-2,2-dimethyl-6-oxo-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-carbaldehyde 在 吡啶 、 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 甲苯 为溶剂， 生成 (1R,2R,6S,7S,10S)-10-Hydroxy-7-iodo-3,9-dioxa-tricyclo[5.2.1.0^2,6]decane-4,8-dione
  参考文献：
  名称：

  Formation of highly substituted cyclopentanes from radical and anionic Michael cyclisations of α-iodo-γ- and -δ-lactones

  摘要：

  alpha-Iodos-delta- and -gamma-hexonolactones with alpha,beta-unsaturated esters developed from C-6 undergo both tributyltin hydride-induced radical and base catalysed anionic Michael cyclisations to form bicyclic lactones with very highly substituted homochiral cyclopentanes. The delta-lactones give cyclopentane products in which adjacent carbon substituents on the cyclopentane ring are cis to each other, whereas gamma-lactones give cyclopentanes in which the carbon chains are trans.

  DOI：

  10.1016/s0040-4039(00)76978-4