2-(4-(2-iodophenyl)butyl)-3-oxocyclohex-1-enyl trifluoromethanesulfonate | 1271193-11-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2-(4-(2-iodophenyl)butyl)-3-oxocyclohex-1-enyl trifluoromethanesulfonate
• CAS: 1271193-11-3
• 化学式: C₁₇H₁₈F₃IO₄S
• 分子量: 502.293
• InChiKey: UTCNZTQRMJCVPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(4-(2-iodophenyl)butyl)-3-oxocyclohex-1-enyl trifluoromethanesulfonate 在 六甲基磷酰三胺 、 正丁基锂 作用下， 以 甲苯 为溶剂， 以46%的产率得到
  参考文献：
  名称：

  Generation of Medium-Ring Cycloalkynes by Ring Expansion of Vinylogous Acyl Triflates

  摘要：

  Reductive cyclization of aryl and vinyl iodides tethered to vinylogous acyl trifiates (VATS) induces a ring-expanding fragmentation to provide cyclic alkynyl ketones, including strained nine-membered cycloalkynes, in fair to excellent yield. The tandem cyclization/C-C bond-cleavage is Initiated under carefully optimized conditions by halogen metal exchange in the presence of carbonyl and vinyl triflate functionality. A modified protocol for alkylation of 1,3-cyclohexanedione is described for preparing the relevant VAT substrates.

  DOI：

  10.1021/ol2003308
• 作为产物：
  描述：

  4-(2-碘苯基)丁醛 在 吡啶 、 L-脯氨酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 2-(4-(2-iodophenyl)butyl)-3-oxocyclohex-1-enyl trifluoromethanesulfonate
  参考文献：
  名称：

  Generation of Medium-Ring Cycloalkynes by Ring Expansion of Vinylogous Acyl Triflates

  摘要：

  Reductive cyclization of aryl and vinyl iodides tethered to vinylogous acyl trifiates (VATS) induces a ring-expanding fragmentation to provide cyclic alkynyl ketones, including strained nine-membered cycloalkynes, in fair to excellent yield. The tandem cyclization/C-C bond-cleavage is Initiated under carefully optimized conditions by halogen metal exchange in the presence of carbonyl and vinyl triflate functionality. A modified protocol for alkylation of 1,3-cyclohexanedione is described for preparing the relevant VAT substrates.

  DOI：

  10.1021/ol2003308