Thiocarbonic acid O-((Z)-(R)-2-methyl-10-oxo-3,4,5,8,9,10-hexahydro-2H-oxecin-4-yl) ester O-phenyl ester | 866044-10-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: Thiocarbonic acid O-((Z)-(R)-2-methyl-10-oxo-3,4,5,8,9,10-hexahydro-2H-oxecin-4-yl) ester O-phenyl ester
• CAS: 866044-10-2
• 化学式: C₁₇H₂₀O₄S
• 分子量: 320.409
• InChiKey: DZANJRQUFICAPD-DVHDDWJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Thiocarbonic acid O-((Z)-(R)-2-methyl-10-oxo-3,4,5,8,9,10-hexahydro-2H-oxecin-4-yl) ester O-phenyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.5h， 以90%的产率得到(-)-phoracantholide-J
  参考文献：
  名称：

  New Silicon-Mediated, Sequential Ring Expansions of n-Sized 2-Cycloalkenones into Hydroxyolefinic n + m + p Medium-Sized Lactones:  Short Synthesis of (−)-Phoracantholide-J

  摘要：

  In only four steps from 2-cyclopentenone and 2-cyclohexenone, sequential three- or four-atom and then one- to three-atom ring enlargements produce nine- to 12-membered hydroxyolefinic lactones on a gram scale. 2-Cyclopentenone undergoes this serial 5 + 3 + 2 process to form 10-membered ring natural (-)-phoracantholide-J in six linear steps and 26% overall yield.

  DOI：

  10.1021/ol051854x
• 作为产物：
  描述：

  (Z)-8-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-3,4,7,8-tetrahydro-oxocin-2-one 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 Thiocarbonic acid O-((Z)-(R)-2-methyl-10-oxo-3,4,5,8,9,10-hexahydro-2H-oxecin-4-yl) ester O-phenyl ester
  参考文献：
  名称：

  New Silicon-Mediated, Sequential Ring Expansions of n-Sized 2-Cycloalkenones into Hydroxyolefinic n + m + p Medium-Sized Lactones:  Short Synthesis of (−)-Phoracantholide-J

  摘要：

  In only four steps from 2-cyclopentenone and 2-cyclohexenone, sequential three- or four-atom and then one- to three-atom ring enlargements produce nine- to 12-membered hydroxyolefinic lactones on a gram scale. 2-Cyclopentenone undergoes this serial 5 + 3 + 2 process to form 10-membered ring natural (-)-phoracantholide-J in six linear steps and 26% overall yield.

  DOI：

  10.1021/ol051854x