cis-4-iodomethyl-3-(1,1-dimethylethyl)tetrahydro-2H-pyran-2-one

• 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: cis-4-iodomethyl-3-(1,1-dimethylethyl)tetrahydro-2H-pyran-2-one
• 化学式: C₁₀H₁₇IO₂
• 分子量: 296.148
• InChiKey: VVNUTKWPVCOPTN-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3,3-二甲基-1-丁酸 在 4-二甲氨基吡啶 三氟化硼乙醚 、 六正丁基二锡 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 cis-4-iodomethyl-3-(1,1-dimethylethyl)tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  On the 6-Exo Atom Transfer Radical Cyclization Reactions of 3-Butenyl 2-Iodoalkanoates

  摘要：

  Bis(tributyltin)-initiated atom transfer cyclization reactions of 3-butenyl iodoalkanoates in the presence of BF3.OEt2 as the catalyst afforded the 6-exo cyclization products as a mixture of 3,4-cis-and trans-substituted tetrahydro-2H-pyran-2-ones in 53-71% Yield with the major isomers being the cis ones. Ab initio calculations at the B3LYP/6-31G* level on the transition states of the radical cyclization and on the cyclized products revealed that the reactions are kinetically controlled and the transition states for the 6-exo radical cyclization are in boat conformations. Moreover, the cis-oriented transition states are of lower energy than the corresponding trans-oriented ones, which are in excellent agreement with experimental results.

  DOI：

  10.1021/jo026381b

文献信息

• On the 6-Exo Atom Transfer Radical Cyclization Reactions of 3-Butenyl 2-Iodoalkanoates
  作者：Xingang Fang、Hairong Xia、Hui Yu、Xicheng Dong、Minbo Chen、Quanrui Wang、Fenggang Tao、Chaozhong Li

  DOI：10.1021/jo026381b

  日期：2002.11.1

  Bis(tributyltin)-initiated atom transfer cyclization reactions of 3-butenyl iodoalkanoates in the presence of BF3.OEt2 as the catalyst afforded the 6-exo cyclization products as a mixture of 3,4-cis-and trans-substituted tetrahydro-2H-pyran-2-ones in 53-71% Yield with the major isomers being the cis ones. Ab initio calculations at the B3LYP/6-31G* level on the transition states of the radical cyclization and on the cyclized products revealed that the reactions are kinetically controlled and the transition states for the 6-exo radical cyclization are in boat conformations. Moreover, the cis-oriented transition states are of lower energy than the corresponding trans-oriented ones, which are in excellent agreement with experimental results.