methyl 4-(diethylphosphono)crotonate | 67629-62-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 4-(diethylphosphono)crotonate
• 英文别名: methyl (E)-4-(diethoxyphosphoryl)but-2-enoate；methyl (2E)-4-(diethoxyphosphoryl)but-2-enoate；(E)-methyl 4-(diethoxyphosphoryl)but-2-enoate；2-Butenoic acid, 4-(diethoxyphosphinyl)-, methyl ester, (2E)-；methyl (E)-4-diethoxyphosphorylbut-2-enoate
• CAS: 67629-62-3
• 化学式: C₉H₁₇O₅P
• 分子量: 236.205
• InChiKey: ISLZPJMIALHMEC-VOTSOKGWSA-N

物化性质

• 沸点：
  315.1±35.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-(diethylphosphono)crotonate 在 palladium on activated charcoal 氢气 、 lithium hexamethyldisilazane 作用下， 以 甲醇 、 苯 为溶剂， 反应 20.17h， 生成 methyl 5-(3-aminophenyl)pentanoate
  参考文献：
  名称：

  An azido-functionalized isocarbacyclin analogue acting as an efficient photoaffinity probe for a prostacyclin receptor

  摘要：

  A stable prostacyclin analogue, (15S)-18c, having an azidophenyl, group as a photoaffinity labeling functionality has been synthesized. This compound has a sufficiently high affinity to the prostacyclin receptor protein in mastocytoma P-815 cells, exhibiting an IC50 value of 3 nM for the replacement of iloprost bound to the receptor protein. A photoaffinity probe compound, [H-3]-(15S)-18c, is obtainable by reduction of the ketone 16c with [H-3]NaBH4-CeCl3 followed by alkaline hydrolysis of the methyl ester.

  DOI：

  10.1016/s0040-4020(01)88526-4
• 作为产物：
  描述：

  巴豆酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 反应 2.0h， 生成 methyl 4-(diethylphosphono)crotonate
  参考文献：
  名称：

  磺胺的全合成，A Piper alkamide

  摘要：

  摘要 sylvamide 的结构 N-isobutyl-4,5-dihydroxy-2(E)-decenamide 已通过其全合成得到证实。赤型立体化学也是通过比较天然和合成样品的性质来建立的。

  DOI：

  10.1016/0031-9422(83)85049-3

文献信息

• Identification and synthesis of the sex pheromone of Phtheochroa cranaodes (Lepidoptera: Tortricidae)
  作者：C. Rikard Unelius、Alvaro Eiras、Peter Witzgall、Marie Bengtsson、Adelécio Kovaleski、Evaldo F. Vilela、Anna-Karin Borg-Karlson

  DOI：10.1016/0040-4039(96)00050-0

  日期：1996.2

  The pheromone of Phtheochroa cranaodes (Lepidoptera: Tortricidae) was identified as (3E,5Z)-3,5-dodecadienyl acetate (5) by GC-MS analysis of female gland extracts and field trapping of males with synthetic compound.

  通过雌性腺体提取物的GC-MS分析和雄性化合物与合成化合物的田间诱捕，将十字花科（鳞翅目：opter科）的信息素鉴定为（3 E，5 Z）-3,5-十二碳烯基乙酸酯（5）。
• Amides of vegetable origin. Part XII. A new series of alka-2,4-dienoic tyramine-amides from Anacyclus pyrethrum D.C. (Compositae)
  作者：R. S. Burden、L. Crombie

  DOI：10.1039/j39690002477

  日期：——

  Anacyclus pyrethrum D.C. (Compositae) contains N-(2′-p-hydroxyphenylethyl) deca-, dodeca-, and tetradeca-trans-2, trans-4-dienamide, a new series of tyramine amides corresponding to isobutylamides which this plant produces. The tyramides, and the corresponding isobutylamides, are synthesised stereospecifically by phosphonatenaion synthesis. Anacyclus pyrethrum is found to contain the lignan (+)-sesamin and attention is drawn to the cooccurrence of lipid (and other) amides with lignans in a number of plants from three families (Compositae, Piperaceae, and Rutaceae).

  安卡菊（Anacyclus pyrethrum D.C.，菊科）含有新系列的酪胺酰胺，即N-(2′-对羟基苯乙基)癸基、十二基和十四基反式-2,反式-4-二烯酰胺，这些化合物对应于该植物产生的异丁基酰胺。酪胺酰胺及其相应的异丁基酰胺是通过磷酸钠特定的立体选择性合成得到的。研究发现，安卡菊中还含有木脂素（+）-芝麻素，并指出在来自三个科（菊科、胡椒科和芸香科）的多种植物中，脂质（及其他）酰胺与木脂素的共存现象值得关注。
• Gb₃Glycosphingolipids with Fluorescent Oligoene Fatty Acids: Synthesis and Phase Behavior in Model Membranes
  作者：Lukas J. Patalag、Jeremias Sibold、Ole M. Schütte、Claudia Steinem、Daniel B. Werz

  DOI：10.1002/cbic.201700414

  日期：2017.11.2

  Get in place! Fluorescent labels can alter the phase behavior of lipids considerably. The synthetic route to fatty acid‐labeled Gb3 derivatives that partition in the liquid‐disordered phase, even after binding of Shiga toxin B subunits, is described.

  到位！荧光标记可以显着改变脂质的相行为。甚至在志贺毒素B亚基结合后，也描述了合成脂肪酸标记的Gb 3衍生物的合成路线，该衍生物在液相混乱的阶段进行分配。
• Imidazolidinones as brain activators
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US04886817A1

  公开（公告）日：1989-12-12

  This invention relates to imidazolidinone compounds of the formula ##STR1## wherein Q is methylene group or a single bond: R is a heterocyclic group selected from the group consisting of pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl and 1,3-thiazolyl which may be unsubstituted or with a substituent selected from the group consisting of lower alkyl, lower alkoxy and halogen atom, wherein R is bonded to Q or, when Q is a single bond, to the imidazolidinone ring, through the carbon atom of R; the ring A is an unsubstituted phenyl or a substituted phenyl having 1 or 2 substituent(s) selected from the group consisting of lower alkyl, lower alkoxy, halogen, lower alkylthio, trihalogeno-lower alkyl and nitro; Y is vinylene group or ethynylene; m is a integer from 1 to 6 and n is 0, 1 or 2, or a pharmacetically acceptable salt thereof. These compounds aer useful as cerebral activators, anti-depressants and nootropic drugs.

  这项发明涉及公式为##STR1##的咪唑啉酮化合物，其中Q是亚甲基基团或单键：R是从吡啶基、吡啶并嗪基、嘧啶基、吡嗪基和1,3-噻唑基中选择的杂环基团，可以是未取代或带有从低烷基、低烷氧基和卤原子中选择的取代基，其中R与Q结合，或者当Q为单键时，与咪唑啉酮环通过R的碳原子结合；环A是未取代苯基或具有1或2个取代基（从低烷基、低烷氧基、卤素、低烷硫基、三卤代低烷基和硝基中选择）的取代苯基；Y是乙烯基或乙炔基；m是从1到6的整数，n为0、1或2，或其药用盐。这些化合物可用作脑活化剂、抗抑郁药和脑力药物。
• Benzocyclization of 2,4-Hexadienoic Acids. Synthesis of (<i>R</i>)-(-)-Curcuphenol Acetate
  作者：D. Murali、G. S. Krishna Rao

  DOI：10.1055/s-1987-27905

  日期：——

  A simple and general benzocyclization sequence, useful in the conversion of α-methylene ketones/aldehydes 1a-f to phenolic acetates 6a-g via the dienoic acids 5a-g is presented. The technique has provided a new route to the terpenoids, thymol acetate (6f) and (R)-(-)-curcuphenol acetate (6g).

  本文介绍了一种简单且通用的苯并环化序列，可用于将α-亚甲基酮/醛1a-f转化为酚酯6a-g，途径是通过二烯酸5a-g。该技术为萜类化合物提供了一条新途径，包括百里香酚乙酸酯（6f）和（R）-(-)-革酚乙酸酯（6g）。