(R)-Iodo-((1R,2S,6S,7R,10R)-1-iodo-4,4-dimethyl-9-oxo-3,5,8-trioxa-tricyclo[5.2.1.0^2,6]dec-10-yl)-acetic acid methyl ester | 157729-76-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-Iodo-((1R,2S,6S,7R,10R)-1-iodo-4,4-dimethyl-9-oxo-3,5,8-trioxa-tricyclo[5.2.1.0^2,6]dec-10-yl)-acetic acid methyl ester
• CAS: 157729-76-5
• 化学式: C₁₂H₁₄I₂O₆
• 分子量: 508.049
• InChiKey: LHVZNAORRQOZQG-XLQPDCHXSA-N

物化性质

• 沸点：
  511.9±50.0 °C(predicted)
• 密度：
  2.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-Iodo-((1R,2S,6S,7R,10R)-1-iodo-4,4-dimethyl-9-oxo-3,5,8-trioxa-tricyclo[5.2.1.0^2,6]dec-10-yl)-acetic acid methyl ester 在 lithium iodide 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到((1R,2S,6S,7R,10S)-1-Iodo-4,4-dimethyl-9-oxo-3,5,8-trioxa-tricyclo[5.2.1.0^2,6]dec-10-yl)-acetic acid methyl ester
  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,7S,7aS)-7-iodo-2,2-dimethyl-6-oxo-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-carbaldehyde 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (R)-Iodo-((1R,2S,6S,7R,10R)-1-iodo-4,4-dimethyl-9-oxo-3,5,8-trioxa-tricyclo[5.2.1.0^2,6]dec-10-yl)-acetic acid methyl ester
  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