(Z)-3-(fluoromethyl)-2-buten-1-ol | 5944-19-4

• 分子结构分类: 有机化合物 - 有机卤素化合物
• 英文名称: (Z)-3-(fluoromethyl)-2-buten-1-ol
• 英文别名: (Z)-3-(fluoromethyl)but-2-en-1-ol；(Z)-3-(fluoromethyl)-2-butenol；(Z)-4-fluoro-3-methylbut-2-en-1-ol
• CAS: 5944-19-4
• 化学式: C₅H₉FO
• 分子量: 104.124
• InChiKey: AMGCWLDRGIJPGL-DJWKRKHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  7
• 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：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-3-(fluoromethyl)-2-buten-1-ol 在 三溴化磷 作用下， 以 乙腈 、 正戊烷 为溶剂， 反应 2.0h， 生成 (Z)-[CH2F]-DMAPP
  参考文献：
  名称：

  Phosphorylation of isoprenoid alcohols

  摘要：

  DOI：

  10.1021/jo00375a005
• 作为产物：
  描述：

  (Z)-3-(fluoromethyl)-2-butenyl methanesulfonate 在 2,6-二甲基吡啶 、 水 作用下， 以 丙酮 为溶剂， 生成 (Z)-3-(fluoromethyl)-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。
• Type II Isopentenyl Diphosphate Isomerase:  Irreversible Inactivation by Covalent Modification of Flavin
  作者：Steven C. Rothman、Jonathan B. Johnston、Sungwon Lee、Joel R. Walker、C. Dale Poulter

  DOI：10.1021/ja7108954

  日期：2008.4.1

  Isopentenyl diphosphate isomerase (IDI) catalyzes the interconversion of isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), the basic building blocks of isoprenoid molecules. Two structurally unrelated classes of IDI are known. Type I IPP isomerase (IDI-1) utilizes a divalent metal in a protonation-deprotonation reaction; whereas, the type II enzyme (IDI-2) requires reduced flavin

  异戊烯二磷酸异构酶 (IDI) 催化异戊烯二磷酸 (IPP) 和二甲基烯丙基二磷酸 (DMAPP) 的相互转化，这是类异戊二烯分子的基本组成部分。两种结构无关的 IDI 类别是已知的。I 型 IPP 异构酶 (IDI-1) 在质子化-去质子化反应中利用二价金属；而 II 型酶 (IDI-2) 需要减少的黄素。环氧、二烯和氟化底物类似物，IDI-1 的不可逆抑制剂，被分析为 IDI-2 的机械探针。3,4-氧化-3-甲基-1-丁基二磷酸酯 (eIPP)、3-亚甲基-4-戊烯-1-基二磷酸酯 (vIPP) 和 3-(氟甲基)-3-丁烯-1-基二磷酸酯 ( fmIPP) 通过与还原的黄素形成共价加合物来灭活 IDI-2。灭活复合物的紫外-可见光谱与 N5 位异咯嗪环的修饰一致。vIPP 和 fmIPP 也是替代底物，异构化与黄素辅因子的烷基化竞争。(Z)-3-(氟甲基)-2-丁烯-1-基二磷酸酯