(1S,2S,5R)-3-chloro-1,2-isopropylidenedioxycyclohex-3-en-5-yl acetate | 1042908-97-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,5R)-3-chloro-1,2-isopropylidenedioxycyclohex-3-en-5-yl acetate
• 英文别名: [(3aS,5R,7aS)-7-chloro-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-yl] acetate
• CAS: 1042908-97-3
• 化学式: C₁₁H₁₅ClO₄
• 分子量: 246.691
• InChiKey: XBXSTKQBPBSPLN-UJNFCWOMSA-N

物化性质

• 沸点：
  307.5±42.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 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：

  甲醇 、 (1S,2S,5R)-3-chloro-1,2-isopropylidenedioxycyclohex-3-en-5-yl acetate 在 碳酸氢钠 、 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到methyl (2S,3S,5R)-5-acetoxy-2,3-isopropylidenedioxy-6-oxohexanoate
  参考文献：
  名称：

  Stereoselective Synthesis of 3-Oxygenated-cis-dialkyl-2,5-substituted Tetrahydrofurans from Cyclohexadienediols

  摘要：

  The 3-oxygenated-cis-dialkyl-2,5-substituted tetrahydrofuran system, present in several natural products, was prepared with good selectivity by acidic cyclization of 5-alkene-1,2,4-triol derivatives. The starting alkenol was obtained in few steps from a chiral cis-diol resulting from microbial oxidation of bromobenzene. The study of the cyclization allowed the rationalization of all experimental results by assuming a complete ionization at the allylic position and a model close to the one proposed by Labelle for homoallylic induction in five-membered ring closures.

  DOI：

  10.1021/jo800514k
• 作为产物：
  描述：

  (1R,2S,5S,5S)-3-chloro-6-iodo-1,2-isopropylidenedioxycyclohex-3-en-5-yl acetate 在 三正丁基氢锡 、 1,1'-偶氮(氰基环己烷) 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以95%的产率得到(1S,2S,5R)-3-chloro-1,2-isopropylidenedioxycyclohex-3-en-5-yl acetate
  参考文献：
  名称：

  Stereoselective Synthesis of 3-Oxygenated-cis-dialkyl-2,5-substituted Tetrahydrofurans from Cyclohexadienediols

  摘要：

  The 3-oxygenated-cis-dialkyl-2,5-substituted tetrahydrofuran system, present in several natural products, was prepared with good selectivity by acidic cyclization of 5-alkene-1,2,4-triol derivatives. The starting alkenol was obtained in few steps from a chiral cis-diol resulting from microbial oxidation of bromobenzene. The study of the cyclization allowed the rationalization of all experimental results by assuming a complete ionization at the allylic position and a model close to the one proposed by Labelle for homoallylic induction in five-membered ring closures.

  DOI：

  10.1021/jo800514k