(4-Methoxy-3,3-dimethylhexa-1,5-dien-2-yl) trifluoromethanesulfonate | 958019-05-1

• 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: (4-Methoxy-3,3-dimethylhexa-1,5-dien-2-yl) trifluoromethanesulfonate
• 英文别名: (4-methoxy-3,3-dimethylhexa-1,5-dien-2-yl) trifluoromethanesulfonate
• CAS: 958019-05-1
• 化学式: C₁₀H₁₅F₃O₄S
• 分子量: 288.288
• InChiKey: BFNCXOJCVHOFPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4-Methoxy-3,3-dimethylhexa-1,5-dien-2-yl) trifluoromethanesulfonate 在 四(三苯基膦)钯 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以30%的产率得到3-methoxy-4,4-dimethyl-5-methylene-cyclopentene
  参考文献：
  名称：

  Functionalized Cyclobutanes via Heck Cyclization

  摘要：

  [GRAPHICS]Heck-type 4-exo-trig cyclization of linear 2-enol triflate-1,5-hexadienes provides functionalized methylene cyclobutanes. Intramolecular palladium coordination can initiate beta-hydride elimination leading to 1,2-dimethylene cyclobutane derivatives, which are obtained with high selectivity if substrates having a geminal diphenyl group at C, are used. In parallel, formal 5-endo-trig cyclization and beta-hydride elimination form 1-methylene cyclopent-2-en derivatives.

  DOI：

  10.1021/ol701697r
• 作为产物：
  描述：

  4-methoxy-3,3-dimethyl-hex-5-en-2-one 、 N-苯基双(三氟甲烷磺酰)亚胺 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 (4-Methoxy-3,3-dimethylhexa-1,5-dien-2-yl) trifluoromethanesulfonate
  参考文献：
  名称：

  Functionalized Cyclobutanes via Heck Cyclization

  摘要：

  [GRAPHICS]Heck-type 4-exo-trig cyclization of linear 2-enol triflate-1,5-hexadienes provides functionalized methylene cyclobutanes. Intramolecular palladium coordination can initiate beta-hydride elimination leading to 1,2-dimethylene cyclobutane derivatives, which are obtained with high selectivity if substrates having a geminal diphenyl group at C, are used. In parallel, formal 5-endo-trig cyclization and beta-hydride elimination form 1-methylene cyclopent-2-en derivatives.

  DOI：

  10.1021/ol701697r

文献信息

• Functionalized Cyclobutanes via Heck Cyclization
  作者：Anna Innitzer、Lothar Brecker、Johann Mulzer

  DOI：10.1021/ol701697r

  日期：2007.10.1

  [GRAPHICS]Heck-type 4-exo-trig cyclization of linear 2-enol triflate-1,5-hexadienes provides functionalized methylene cyclobutanes. Intramolecular palladium coordination can initiate beta-hydride elimination leading to 1,2-dimethylene cyclobutane derivatives, which are obtained with high selectivity if substrates having a geminal diphenyl group at C, are used. In parallel, formal 5-endo-trig cyclization and beta-hydride elimination form 1-methylene cyclopent-2-en derivatives.