(E)-4-Dimethylphosphono-3-methyl-2-butenoate | 62924-29-2

• 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: (E)-4-Dimethylphosphono-3-methyl-2-butenoate
• 英文别名: trimethyl 3-methyl-4-phosphonocrotonate；methyl-4-dimethylphosphono-3-methylcrotonate；methyl (E)-4-dimethoxyphosphoryl-3-methylbut-2-enoate
• CAS: 62924-29-2
• 化学式: C₈H₁₅O₅P
• 分子量: 222.178
• InChiKey: USJWHHILBYSBHA-FNORWQNLSA-N

物化性质

• 沸点：
  112-118 °C(Press: 0.3 Torr)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (E)-4-Dimethylphosphono-3-methyl-2-butenoate 在 氢氧化钾 作用下， 生成 9,10-二氢维甲酸
  参考文献：
  名称：

  Dihydroretinoic acids and their derivatives. Synthesis and biological activity

  摘要：

  The syntheses of the ring and four side-chain dihydroretinoic acids and/or their esters, 3-7, are described. The syntheses of several other retinoids containing a substituted aromatic ring are also included. The biological activity of the compounds was evaluated in vivo in a chemically induced mouse skin papilloma test and in vitro in two vitamin A deficient assays. The activity observed for 1a, 1c, and 2a in the former test was partially retained in the dihydro derivatives 4b, 4c, and 6b. Similar results were found in the in vitro assays.

  DOI：

  10.1021/jm00217a011

文献信息

• Fluorinated retinoic acids and their analogs. 1. Synthesis and biological activity of (4-methoxy-2,3,6-trimethylphenyl)nonatetraenoic acid analogs
  作者：Beverly A. Pawson、Ka-Kong Chan、James DeNoble、Ru Jen L. Han、Virginia Piermattie、Anthony C. Specian、Srisamorn Srisethnil、Patrick W. Trown、Oksana Bohoslawec

  DOI：10.1021/jm00195a010

  日期：1979.9

  (4-Methoyx-2,3,6-trimethylphenyl)nonatetraenoic acids, esters, and amides (analogues of retinoic acid) bearing a fluorine atom(s) or a trifluoromethyl group on the polyene side chain were synthesized. The biological activities of these compounds and of 10-, 12-, and 14-fluororetinoic acid esters were evaluated in vivo in a chemically induced mouse papilloma test; the toxicities were assessed in an

  合成了在多烯侧链上带有氟原子或三氟甲基的（4-甲基-2,3,6-三甲基苯基）壬酸酯链烯酸，酯和酰胺（视黄酸的类似物）。在化学诱导的小鼠乳头状瘤试验中评估了这些化合物以及10-，12-和14-氟维甲酸酸酯的生物活性。在体内小鼠维生素A超试验中评估了毒性。发现1c（12-氟维甲酸乙酯）和23和39（分别为芳族4和6-氟维甲酸酯）的抗乳头瘤瘤活性大于母体非氟化酯。相对于2，分别观察到71和72（芳族4-和6-氟视黄酸）和73（相对于4）的抗乳头瘤瘤活性增加。
• Fluorinated retinoic acids and their analogs. 3. Synthesis and biological activity of aromatic 6-fluoro analogs
  作者：Allen J. Lovey、Beverly A. Pawson

  DOI：10.1021/jm00343a014

  日期：1982.1

  Several analogues (15a--e) of methyl (E,E,Z,E)-3,7-dimethyl-6-fluoro-9-(4-methoxy-2,3,6-trimethylphenyl)nonatetraenoate (15f), which had been found to cause a marked regression of chemically induced skin papillomas in mice, were prepared. Two synthetically versatile methods leading to these derivatives are described. The key intermediate, ethyl (Z)-2-fluoro-3-methyl-4,4-dimethoxy-2-butenoate (8), was

  （E，E，Z，E）-3,7-二甲基-6-氟-9-（4-甲氧基-2,3,6-三甲基苯基）壬酸酯（15f）的几种类似物（15a-e），制备了已发现可引起小鼠化学诱导的皮肤乳头状瘤明显退缩的药物。描述了导致这些衍生物的两种合成通用方法。将关键中间体（Z）-2-氟-3-甲基-4,4-二甲氧基-2-丁烯酸酯（8）精制为C10醛酯，甲基（2E，4E，6Z）-3-甲基-6-氟-7-甲酰基-2,4,6-辛三烯酸酯（14a），经Wittig与芳基phosph盐13a-e缩合后得到（2E，4E，6Z，8E）-3,7-二甲基-6-氟-9-芳基-2,4,6,8-壬酸酯15a-e。或者，将8与[（4-甲氧基-2,3,6-三甲基苯基）甲基]三苯基氯化chloride（13f）的Wittig反应得到（E / Z，E）-2-氟-3-甲基-5-的混合物（2,3，6-三甲基-4-甲氧基苯基）-2,4-戊二烯酸酯17和18，将
• Fluorinated polyenes, their preparation and pharmaceutical compositions containing them
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0009539A1

  公开（公告）日：1980-04-16

  Compounds of the formula wherein R is a moiety of one of the formulae and wherein one of R1 and R is fluorine and the other is hydrogen; R3 is formyl, hydroxy-methyl, alkoxymethyl, alkanoyloxymethyl, carboxyl, alkoxycarbonyl, carbamoyl, mono(lower alkyl)-carbamoyl or di-(lower alkyl) carbamoyl; at least one of R', R5 and R7 is halogen and the others are hydrogen or lower alkyl; R6 is lower alkyl or lower alkoxy; R8 and R each are lower alkyl; R9 is hydrogen or lower alkyl; and R10 is oxygen or sulphur; with the proviso that when R is alkoxycarbonyl and R10 is sulphur, the compound is all trans; or pharmaceutically acceptable salts thereof, are useful in the treatment of tumors and acne. They are prepared by Wittig or Horner reaction from an aliphatic and an aromatic component.

  式中的化合物 其中 R 是式中的一个分子 其中 R1 和 R 中的一个是氟，另一个是氢；R3 是甲酰基、羟甲基、烷氧基甲基、烷酰氧基甲基、羧基、烷氧羰基、氨基甲酰基、单（低级烷基）氨基甲酰基或二（低级烷基）氨基甲酰基；R'、R5 和 R7 中至少有一个是卤素，其它是氢或低级烷基；R6为低级烷基或低级烷氧基；R8和R各自为低级烷基；R9为氢或低级烷基；R10为氧或硫；但当R为烷氧基羰基且R10为硫时，化合物为全反式；或其药学上可接受的盐，可用于治疗肿瘤和痤疮。它们由脂肪族成分和芳香族成分通过 Wittig 或 Horner 反应制备而成。
• Mori, Kenji; Takahashi, Yoshio, Liebigs Annalen der Chemie, 1991, # 10, p. 1057 - 1065
  作者：Mori, Kenji、Takahashi, Yoshio

  DOI：——

  日期：——
• Ionic photodissociation of polyenes via a highly polarized singlet excited state
  作者：A. Mahipal Reddy、V. Jayathirtha Rao

  DOI：10.1021/jo00051a011

  日期：1992.12

  Several polyene acetates and polyene methyl ether were prepared. Upon direct excitation these polyenes undergo ionic photodissociation from their singlet excited states. Triplet-sensitization experiments on these polyenes revealed that the ionic photodissociation process is restricted to singlet excited states. The rationale put forward is that the polyene chromophore undergoes charge separation/polarization in the singlet excited state, which leads to ionic photodissociation.