2-(2-iodobenzyl)-3-oxocyclohex-1-enyl trifluoromethanesulfonate | 1271192-90-5

• 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-(2-iodobenzyl)-3-oxocyclohex-1-enyl trifluoromethanesulfonate
• 英文别名: [2-[(2-Iodophenyl)methyl]-3-oxocyclohexen-1-yl] trifluoromethanesulfonate
• CAS: 1271192-90-5
• 化学式: C₁₄H₁₂F₃IO₄S
• 分子量: 460.213
• InChiKey: HJCHZWHIVJKEBD-UHFFFAOYSA-N

物化性质

• 熔点：
  44-46 °C
• 沸点：
  474.4±45.0 °C(Predicted)
• 密度：
  1.81±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-iodobenzyl)-3-oxocyclohex-1-enyl trifluoromethanesulfonate 在 正丁基锂 、 对甲苯磺酸 作用下， 以 甲醇 、 六甲基磷酰三胺 、 甲苯 为溶剂， 反应 18.0h， 生成 2,3,4,9-tetrahydro-1H-fluoren-1-one
  参考文献：
  名称：

  Strain-Promoted Azide–Alkyne Cycloadditions of Benzocyclononynes

  摘要：

  Preliminary studies related to the design and development of new cycloalkyne reagents for metal-free click coupling are reported. Cydononynes are more stable than cyclooctynes, and the robust benzocyclononyne platform offers spontaneous reactivity toward azides at rates competitive with other azidophiles that have been employed for metal-free click coupling. Benzocyclononynes (e.g., 1) provide valuable insight into the design of new cycloalkynes for strain-promoted azide-alkyne cydoaddition (SPAAC) couplings for applications in which side reactions and decomposition of the reagent must be kept to a minimum.

  DOI：

  10.1021/jo300188y
• 作为产物：
  描述：

  1,3-环己二酮 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 2-(2-iodobenzyl)-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