7,8-didehydro-6,9,10,11-tetrahydro-5H-benzo[10]annulen-12-one | 1271193-57-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7,8-didehydro-6,9,10,11-tetrahydro-5H-benzo[10]annulen-12-one
• CAS: 1271193-57-7
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: FKATUDSEOLJTAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(2-碘苯基)乙酸甲酯 在 吡啶 、 六甲基磷酰三胺 、 正丁基锂 、 二异丁基氢化铝 、 L-脯氨酸 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 7,8-didehydro-6,9,10,11-tetrahydro-5H-benzo[10]annulen-12-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

文献信息

• Generation of Medium-Ring Cycloalkynes by Ring Expansion of Vinylogous Acyl Triflates
  作者：Jumreang Tummatorn、Gregory B. Dudley

  DOI：10.1021/ol2003308

  日期：2011.3.18

  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.