(E)-2,2-dimethyl-1,3-propanediyl α-acetyl-2-(trifluoromethyl)styrylphosphonate | 115578-88-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2,2-dimethyl-1,3-propanediyl α-acetyl-2-(trifluoromethyl)styrylphosphonate
• 英文别名: 5,5-dimethyl-2-[1-(2-trifluoromethylbenzylidene)acetonyl]-2-oxo-1,3,2-dioxaphosphorinane；(E)-3-(5,5-dimethyl-2-oxo-1,3,2lambda5-dioxaphosphinan-2-yl)-4-[2-(trifluoromethyl)phenyl]but-3-en-2-one；(E)-3-(5,5-dimethyl-2-oxo-1,3,2λ5-dioxaphosphinan-2-yl)-4-[2-(trifluoromethyl)phenyl]but-3-en-2-one
• CAS: 115578-88-6
• 化学式: C₁₆H₁₈F₃O₄P
• 分子量: 362.285
• InChiKey: VVSNLPHHKDNJKK-RIYZIHGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-2,2-dimethyl-1,3-propanediyl α-acetyl-2-(trifluoromethyl)styrylphosphonate 生成 2-ethyl 5-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydro-2,6-dimethyl-4-(2-trifluoromethylphenyl)-3-pyridinecarboxylate
  参考文献：
  名称：

  1,4-Dihydropyridine-3-carboxylate derivatives

  摘要：

  1,4-二氢吡啶-3-羧酸衍生物具有扩血管和降压作用。

  公开号：

  US05036059A1
• 作为产物：
  描述：

  2-氯-5,5-二甲基-1,3,2-二氧磷杂环己烷 在 哌啶乙酸盐 三乙胺 作用下， 以 乙醚 、 苯 为溶剂， 反应 3.0h， 生成 (E)-2,2-dimethyl-1,3-propanediyl α-acetyl-2-(trifluoromethyl)styrylphosphonate
  参考文献：
  名称：

  Synthesis and antihypertensive activities of 1,4-dihydropyridine-5-phosphonate derivatives. II.

  摘要：

  合成了一系列1,4-二氢吡啶-5-环状磷酸酯衍生物，作为1,4-二氢吡啶-3,5-二羧酸钙拮抗剂的类似物，并对其抗高血压活性进行了检查。几种化合物在降低正常血压和自发性高血压大鼠（SHR）的血压方面被证明具有优于或可比于硝苯地平的活性。在这些化合物中，甲基2,6-二甲基-5-(2-氧-1,3,2-二氧磷烷-2-基)-4-(2-硝基苯基)-1,4-二氢吡啶-3-羧酸酯（31，DHP-218）在SHR中的活性约为硝苯地平的7倍，并被选为进一步开发和临床评估的候选化合物。讨论了结构-活性关系。

  DOI：

  10.1248/cpb.35.4144

文献信息

• Novel Synthesis of α-Acetylstyrylphosphonates
  作者：Ryozo Sakoda、Hiroo Matsumoto、Kiyotomo Seto

  DOI：10.1055/s-1993-25926

  日期：——

  α-Acetylstyrylphosphonates were conveniently synthesized from 2-oxopropylphosphonates and substituted (dimorpholinomethyl)-benzenes (aminals). 4-Benzylidenemorpholinium carboxylates, generated from aminals by the action of α-halo acids, reacted with the phosphonates to give the products by elimination of the amine. The yields were influenced by the nature of substituents and their position in the phenyl ring and could be improved by adjustment of the acidities of the reacted acids. α-Acetylstyrylphosphonates containing various substituents on every position (at the 2-, 3-, or 4-position) in the phenyl ring were obtained generally in excellent yields using monochloroacetic acid.

  α-Acetylstyryl磷酸酯可以通过2-氧代丙基磷酸酯和取代的（二吗啉甲基）苯（氨基缩醛）方便地合成。在α-卤代酸的作用下，从氨基缩醛生成的4-苄叉吗啉鎓羧酸酯与磷酸酯反应，通过消除胺得到产物。产率受取代基的性质及其在苯环中的位置影响，并且可以通过调整反应酸的酸度来提高。使用单氯乙酸，通常可以以优异的产率获得在苯环的2-、3-或4-位置上含有各种取代基的α-Acetylstyryl磷酸酯。
• MORITA, IWAO;KUNIMOTO, KATSUTOSHI;TSUDA, MASAMI;TADA, SHIN-ICHI;KISE, MAS+, CHEM. AND PHARM. BULL., 35,(1987) N 10, 4144-4154
  作者：MORITA, IWAO、KUNIMOTO, KATSUTOSHI、TSUDA, MASAMI、TADA, SHIN-ICHI、KISE, MAS+

  DOI：——

  日期：——
• US5036059A
  申请人：——

  公开号：US5036059A

  公开（公告）日：1991-07-30
• Synthesis and antihypertensive activities of 1,4-dihydropyridine-5-phosphonate derivatives. II.
  作者：IWAO MORITA、KATSUTOSHI KUNIMOTO、MASAMI TSUDA、SHIN-ICHI TADA、MASAHIRO KISE、KIYOSHI KIMURA

  DOI：10.1248/cpb.35.4144

  日期：——

  A series of 1, 4-dihydropyridine-5-cyclic phosphonate derivatives, designed as analogues of 1, 4- dihydropyridine-3, 5-dicarboxylate calcium antagonists, was synthesized and examined for antihypertensive activity. Several compounds were proved to have activities superior or comparable to that of nifedipine in lowering blood pressure in normotensive and spontaneously hypertensive rats (SHR). Among these compounds, methyl 2, 6-dimethyl-5- (2-oxo-1, 3, 2-dioxaphosphorinan-2-yl) -4- (2-nitrophenyl) -1, 4-dihydropyridine-3-carboxylate (31, DHP-218) was approximately 7 times more active than nifedipine in SHR and was selected for further development and clinical evaluation. The structure-activity relationships are discussed.

  合成了一系列1,4-二氢吡啶-5-环状磷酸酯衍生物，作为1,4-二氢吡啶-3,5-二羧酸钙拮抗剂的类似物，并对其抗高血压活性进行了检查。几种化合物在降低正常血压和自发性高血压大鼠（SHR）的血压方面被证明具有优于或可比于硝苯地平的活性。在这些化合物中，甲基2,6-二甲基-5-(2-氧-1,3,2-二氧磷烷-2-基)-4-(2-硝基苯基)-1,4-二氢吡啶-3-羧酸酯（31，DHP-218）在SHR中的活性约为硝苯地平的7倍，并被选为进一步开发和临床评估的候选化合物。讨论了结构-活性关系。
• 1,4-Dihydropyridine-3-carboxylate derivatives
  申请人：Nippon Shinyaku Company, Limited

  公开号：US05036059A1

  公开（公告）日：1991-07-30

  1,4-Dihydropyridine-3-carboxylate derivatives are produced having vasodilating and hypotensive action.

  1,4-二氢吡啶-3-羧酸衍生物具有扩血管和降压作用。