(E)-2-fluoro-2-butenal | 63995-86-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2-fluoro-2-butenal
• 英文别名: (Z)-2-fluoro-2-butenal；2-fluoro-2-butenal；(Z)-2-fluoro-but-2-enal；(Z)-2-fluorocrotonaldehyde；Z-2-Fluor-2-butenal；(2Z)-2-fluorobut-2-enal；(Z)-2-fluorobut-2-enal
• CAS: 63995-86-8
• 化学式: C₄H₅FO
• 分子量: 88.0815
• InChiKey: QHVYVQRIAQVFIB-RQOWECAXSA-N

物化性质

• 沸点：
  96.4±15.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-fluoro-2-butenal 生成 2-fluoro-trans-crotonic acid
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl (Z)-2-fluorobut-2-enoate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 (E)-2-fluoro-2-butenal
  参考文献：
  名称：

  Preparation and opioid activity of analogs of the analgesic dipeptide 2,6-dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alaninamide

  摘要：

  A number of analogues of the recently disclosed analgesic dipeptide 2,6-dimethyl-L-tyrosyl-D-alanine-phenylpropylamide (SC-39566,2) were prepared. These analogues contained oxymethylene, aminomethylene, ketomethylene, bismethylene, and trans double bond (including vinyl fluoride) isosteric replacements for the amide bond between the D-alanine and phenylpropylamine units in 2. These compounds were tested in opioid binding assays and in the mouse writhing assay for analgesic activity. Though not as potent as 2, the oxymethylene, and trans double bond isosteres showed analgesic activity. The aminomethylene analogues also showed binding activity in subnanomolar concentrations at the mu-receptor. The amide bond between 2,6-dimethyl-L-tyrosine and D-alanine units seems to be critical for opioid activity.

  DOI：

  10.1021/jm00080a005

文献信息

• [4+2]-Cycloaddition reactions employing 2-fluoro-2-alkenal N,N-dimethylhydrazones: synthesis of 3-fluoropyridines and dihydro or tetrahydro derivatives thereof
  作者：Somnath Ghosh、Manfred Schlosser

  DOI：10.1016/0022-1139(93)02932-5

  日期：1994.4

  N,N-Dimethylhydrazones prepared from 2-fluoro-2-alkenals undergo smooth [4+2]-cycloaddition reactions with methyl acrylate, dimethyl acetylenedicarboxylates and quinones. The resulting 3-fluoropyridines, or dihydro and tetrahydro derivatives thereof, can be isolated in fair to good yield.

  由2-氟-2-烯烃制备的N，N-二甲基hydr与丙烯酸甲酯，乙炔二羧酸二甲酯和醌进行平滑的[4 + 2]-环加成反应。所得到的3-氟吡啶或其二氢和四氢衍生物可以公平地分离到良好的收率。
• Substituted propane-phosphinic acid compounds
  申请人：Ciba-Geigy Corporation

  公开号：US05064819A1

  公开（公告）日：1991-11-12

  Compounds of the formula I ##STR1## wherein R denotes an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic or araliphatic radical having 2 or more carbon atoms, and wherein one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen or an aliphatic, cycloaliphatic, araliphatic or aromatic radical, another one of R.sup.1, R.sup.2 and R.sup.3 is hydrogen or, in the case of R.sup.1 and R.sup.2, is hydroxy, and the remaining one of R.sup.1, R.sup.2 and R.sup.3 is hydrogen, or wherein R denotes methyl, R.sub.1 denotes hydrogen or hydroxy, R.sub.2 denotes an aromatic radical and R.sub.3 represents hydrogen, and their salts have GABA.sub.B -antagonistic properties and can be used as GABA.sub.B -antagonists. They are obtained when in a compound of formula II ##STR2## in which R, R.sup.1, R.sup.2 and R.sup.3 have their previous significances, Z represents --NH.sub.2 and R.sup.4 denotes a hydroxy-protective group R.sup.5 or, when R.sup.1 and R.sup.3 denote hydrogen and R.sup.2 denotes hydrogen or alkyl, denotes an alkali metal or ammonium ion R.sup.6, or Z represents a protected or latent amino group Z.sup.0 and R.sup.4 denotes hydrogen or a hydroxy-protective group R.sup.5, any group R.sup.5 or R.sup.6 is replaced by hydrogen, and/or any group Z.sup.0 is converted into --NH.sub.2.

  公式I的化合物##STR1##其中R表示具有2个或更多碳原子的脂肪族、环脂族、环脂族-脂肪族或芳基脂肪基，其中R.sup.1、R.sup.2和R.sup.3中的一个代表氢或脂肪族、环脂族、芳基脂肪基或芳香族基，R.sup.1、R.sup.2和R.sup.3中的另一个是氢或在R.sup.1和R.sup.2的情况下是羟基，而R.sup.1、R.sup.2和R.sup.3中的剩余一个是氢，或者R表示甲基，R.sub.1表示氢或羟基，R.sub.2表示芳基，R.sub.3表示氢，它们的盐具有GABA.sub.B-拮抗性质，可用作GABA.sub.B-拮抗剂。当在公式II的化合物中获得它们##STR2##其中R、R.sup.1、R.sup.2和R.sup.3具有其先前的含义，Z表示--NH.sub.2，R.sup.4表示羟基保护基R.sup.5或者当R.sup.1和R.sup.3表示氢且R.sup.2表示氢或烷基时，表示碱金属或铵离子R.sup.6，或者Z表示受保护或潜在的氨基Z.sup.0且R.sup.4表示氢或羟基保护基R.sup.5，任何一个R.sup.5或R.sup.6基团被氢取代，和/或任何一个Z.sup.0基团被转化为--NH.sub.2。
• Synthesis of dienic fluorinated analogs of insect sex pheromones
  作者：Francisco Camps、Jose Coll、Gemma Fabrias、Angel Guerrero

  DOI：10.1016/s0040-4020(01)91296-7

  日期：1984.1

  Synthesis of fluorinated analogs of some dienic insect sex pherormones through a stereocontrolled Wittig reaction of β-fluorinated aldehydes with the appropriate ω-functionalized ylides is reported. Some features of the 1H and 19F NMR spectra of these analogs are also discussed.

  据报道，通过β-氟化醛与适当的ω-官能化的乙炔的立体控制的Wittig反应，合成了一些二齿昆虫性信息素的氟化类似物。还讨论了这些类似物的1 H和19 F NMR光谱的某些特征。
• Solvolytic Ring-opening of Alkoxychlorofluorocyclopropanes: A Ready Access to Fluorinated α,β-Unsaturated Aldehydes and Ketones
  作者：Yvonne Bessière、Dang Ngoc-Huê Savary、Manfred Schlosser

  DOI：10.1002/hlca.19770600528

  日期：1977.7.13

  Alkoxychlorofluorocyclopropanes are easily prepared by chlorofluorocarbene addition to en-ethers in a two-phase system and converted by simple heating in an aqueous solvent mixture to 2-fluoro-2-alkenals which can be reduced to the corresponding alcohols.

  烷氧基氯氟环丙烷很容易通过在两相体系中将氯氟卡宾加成至醚中来制备，并通过在水性溶剂混合物中简单加热而转化为2-氟-2-烯基，该2-氟-2-烯基可以还原为相应的醇。
• THE YLID ROUTE TO FLUORODIENES
  作者：Kazumi Kondo、Sylvain Cottens、Manfred Schlosser

  DOI：10.1246/cl.1984.2149

  日期：1984.12.5

  The readily accessible 2-fluoro-2-alkenals react with phosphorus ylids at approximately the same rate and leading to nearly the same (Z/E)-mixtures of products as the corresponding halogen-free aldehydes do. Thus, the Wittig reaction allows to prepare a great variety of 2-fluorodienes with high yields.

  易于获得的 2-氟-2-烯醛与磷叶立德以大致相同的速率反应，并产生与相应的无卤醛几乎相同的 (Z/E)-产物混合物。因此，Wittig 反应允许以高产率制备多种 2-氟二烯。

表征谱图