(Z)-2-(3-iodo-3-phenylallyl)-3-oxocyclohex-1-enyl trifluoromethanesulfonate | 1271192-93-8

• 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: (Z)-2-(3-iodo-3-phenylallyl)-3-oxocyclohex-1-enyl trifluoromethanesulfonate
• CAS: 1271192-93-8
• 化学式: C₁₆H₁₄F₃IO₄S
• 分子量: 486.25
• InChiKey: DPMRFTZAKYVNQB-RAXLEYEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (Z)-2-(3-iodo-3-phenylallyl)-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44%的产率得到2-phenylcyclonon-2-en-5-yn-1-one
  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：

  (Z)-(3-bromo-1-iodo-2-methylprop-1-enyl)benzene 在 吡啶 、 苄基三甲基氢氧化铵 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 (Z)-2-(3-iodo-3-phenylallyl)-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