(E)-3-(difluoromethyl)-2-buten-1-ol | 104715-28-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-(difluoromethyl)-2-buten-1-ol
• 英文别名: (E)-3-(difluoromethyl)but-2-en-1-ol；(E)-3-(difluoromethyl)-2-butenol；(E)-4,4-difluoro-3-methylbut-2-en-1-ol
• CAS: 104715-28-8
• 化学式: C₅H₈F₂O
• 分子量: 122.115
• InChiKey: ZMEUXSLZELGHST-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(difluoromethyl)-2-buten-1-ol 在 三溴化磷 作用下， 以 正戊烷 为溶剂， 以73%的产率得到2-丁烯,4-溴-1,1-二氟-2-甲基-,(E)-
  参考文献：
  名称：

  Phosphorylation of isoprenoid alcohols

  摘要：

  DOI：

  10.1021/jo00375a005
• 作为产物：
  描述：

  ethyl (E)-3-(difluoromethyl)but-2-enoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 1.0h， 生成 (E)-3-(difluoromethyl)-2-buten-1-ol
  参考文献：
  名称：

  Dimethylallyltryptophan synthase. An enzyme-catalyzed electrophilic aromatic substitution

  摘要：

  Dimethylallyltryptophan (DMAT) synthase catalyzes the alkylation of L-tryptophan at C(4) by dimethylallyl diphosphate (DMAPP) in the first pathway-specific step in the biosynthesis of ergot alkaloids. The mechanism of the reaction was studied with analogs of both substrates. Five 7-substituted derivatives of N-acetyltryptophan (2, Z = OCH3, CH3, F, CF3, and NO2) were synthesized. The L enantiomers of the free amino acids were obtained by selective hydrolysis of the racemate using aminoacylase from Aspergillus. In addition, the E and Z fluoromethyl and difluoromethyl analogs of DMAPP (1, Y = CH3, CH2F, CHF2) were prepared. Rates of the enzyme-catalyzed reactions were measured for the dimethylallyl derivatives with L-tryptophan and for the L-tryptophan derivatives with DMAPP. In addition, the relative reactivities of the methanesulfonate derivatives of the DMAPP analogs were determined for solvolysis in aqueous acetone. A Hammett plot for the tryptophan analogs gave a good linear correlation with rho = -2.0. In addition, a Hammett plot of the logarithms of the relative rates of solvolysis and enzyme-catalyzed alkylation gave a positive linear correlation. These results indicate that the prenyl-transfer reaction catalyzed by DMAT synthase is an electrophilic aromatic substitution and is mechanistically similar to the electrophilic alkylation catalyzed by farnesyl diphosphate synthase.

  DOI：

  10.1021/ja00045a004

文献信息

• Fluorinated Isopentenyladenines: Synthesis and Cytokinin Activity
  作者：Laurence Marival-Hodebar、Marc Tordeux、Claude Wakselman、Marylène Dias、René Mornet、Michel Laloue

  DOI：10.1002/ijch.199900020

  日期：——

  Analogs of N6-isopentenyladenine bearing one or two fluorine atoms at the allylic position were synthesized from simple fluorinated ketones. The monofluoro analog was found to be more active than N6-isopentenyladenine and equivalent to the more potent zeatin, another natural plant growth hormone. The difluoro analog was even more powerful than zeatin.

  由简单的氟化酮合成了在烯丙基位置带有一个或两个氟原子的N 6-异戊烯腺嘌呤的类似物。发现单氟类似物比N 6-异戊烯腺嘌呤更具活性，并且与更有效的玉米素（另一种天然植物生长激素）相当。二氟类似物甚至比玉米蛋白更有效。