2,4,6-trimethylphenyl 4-bromo-4,4,-difluorocrotonate | 158725-01-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2,4,6-trimethylphenyl 4-bromo-4,4,-difluorocrotonate
• 英文别名: (2,4,6-trimethylphenyl) (E)-4-bromo-4,4-difluorobut-2-enoate
• CAS: 158725-01-0
• 化学式: C₁₃H₁₃BrF₂O₂
• 分子量: 319.146
• InChiKey: VZTSHKBCYWSBFA-SNAWJCMRSA-N

物化性质

• 沸点：
  369.7±42.0 °C(predicted)
• 密度：
  1.408±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4,6-trimethylphenyl 4-bromo-4,4,-difluorocrotonate 在 三乙基硼 、 硼烷 、 氧气 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 生成 (1S,3R)-2,2-Difluoro-3-(2-hydroxy-ethyl)-cyclopropanecarboxylic acid 2,4,6-trimethyl-phenyl ester
  参考文献：
  名称：

  Regio- and stereoselective synthesis of gem-difluorocyclopropanes using 4-bromo-4,4-difluorocrotonate

  摘要：

  Regio- and stereoselective formation of the functionalized gem-difluorocyclopropane derivative was achieved through the Michael addition of lithium enolate of ester or amide with 4-bromo-4,4-difluorocrotonate I followed by the triethylborane-O-2 mediated intramolecular substitution reaction.

  DOI：

  10.1016/s0040-4039(00)75998-3
• 作为产物：
  描述：

  bromodifluoroacetaldehyde 、 2,4,6-trimethylphenyl diethylphosphonoacetate 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以70%的产率得到2,4,6-trimethylphenyl 4-bromo-4,4,-difluorocrotonate
  参考文献：
  名称：

  Regio- and stereoselective synthesis of gem-difluorocyclopropanes using 4-bromo-4,4-difluorocrotonate

  摘要：

  Regio- and stereoselective formation of the functionalized gem-difluorocyclopropane derivative was achieved through the Michael addition of lithium enolate of ester or amide with 4-bromo-4,4-difluorocrotonate I followed by the triethylborane-O-2 mediated intramolecular substitution reaction.

  DOI：

  10.1016/s0040-4039(00)75998-3

文献信息

• Asymmetric synthesis of difluorocyclopropanes
  作者：Takeo Taguchi、Akira Shibuya、Hirofumi Sasaki、Jun-ichi Endo、Tsutomu Morikawa、Motoo Shiro

  DOI：10.1016/0957-4166(94)80101-0

  日期：1994.8

  A highly diastereoselective synthesis of functionalized trans gem-difluorocyclopropane carboxylate 3 was achieved through sequential Michael addition of lithium enolate of homochiral N-acylimidazolidinone 2 with 2,4,6-trimethylphenyl (TMP) 4-bromo-4,4-difluorocrotonate 1 and triethylborane-mediated intramolecular substitution reaction.
• Regio- and stereoselective synthesis of gem-difluorocyclopropanes using 4-bromo-4,4-difluorocrotonate
  作者：Takeo Taguchi、Hirofumi Sasaki、Akira Shibuya、Tsutomu Morikawa

  DOI：10.1016/s0040-4039(00)75998-3

  日期：1994.1

  Regio- and stereoselective formation of the functionalized gem-difluorocyclopropane derivative was achieved through the Michael addition of lithium enolate of ester or amide with 4-bromo-4,4-difluorocrotonate I followed by the triethylborane-O-2 mediated intramolecular substitution reaction.