(3,4-二甲氧基苯乙基)脲 | 25017-47-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (3,4-二甲氧基苯乙基)脲
• 英文名称: 1-(3,4-dimethoxyphenethyl)urea
• 英文别名: Urea, (3,4-dimethoxyphenethyl)-；2-(3,4-dimethoxyphenyl)ethylurea
• CAS: 25017-47-4
• 化学式: C₁₁H₁₆N₂O₃
• mdl: MFCD00238985
• 分子量: 224.26
• InChiKey: MDAOEGJTBPQGCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3,4-二甲氧基苯乙基)脲 在 sodium hydroxide 、 sodium ethanolate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 24.5h， 生成 2-butoxy-9,10-dimethoxy-6,7-dihydro-4H-pyrimido<6,1-a>isoquinolin-4-one
  参考文献：
  名称：

  Trequinsin, a potent new antihypertensive vasodilator in the series of 2-(arylimino)-3-alkyl-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido[6,1-a]isoquinolin-4-ones

  摘要：

  Series of 3-substituted-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido [6,1-a]isoquinoline-2,4-diones and 2-substituted-9,10-dimethoxy-6,7-dihydro-4H-pyrimido [6,1-a]isoquinolin-4-ones were synthesized and tested for blood pressure lowering properties in anesthetized normotensive cats and conscious spontaneously hypertensive rats. Several compounds in the 2-(arylamino)-9,10-dimethoxy-6,7-dihydro-4H-pyrimido [6,1-a]isoquinolin-4-one series display a high order of activity. The most active compounds are the alkyl derivatives of the 2-mesitylamino/2-mesitylimino tautomeric forms. The 2-(mesitylimino)-3-methyl analogue trequinsin is a potent antihypertensive agent and displays a hemodynamic profile characteristic of an arteriolar dilator. It is also a potent inhibitor of both cAMP phosphodiesterase and platelet aggregation.

  DOI：

  10.1021/jm00377a016
• 作为产物：
  描述：

  3-(3,4-dimethoxy-phenyl)-propionyl chloride 在 sodium azide 、 氨 、 水 、 丙酮 、 苯 作用下， 生成 (3,4-二甲氧基苯乙基)脲
  参考文献：
  名称：

  Fries; Bestian, Justus Liebigs Annalen der Chemie, 1938, vol. 533, p. 72,83

  摘要：

  DOI：

文献信息

• Elaboration of 1-benzoyltetrahydroisoquinoline derivatives employing a Pictet–Spengler cyclization with α-chloro-α-phenylthioketones. Synthesis of O-methylvelucryptine
  作者：Claudio C Silveira、Carmem R Bernardi、Antonio L Braga、Teodoro S Kaufman

  DOI：10.1016/s0040-4039(01)01998-0

  日期：2001.12

  N-tosyl-β-phenethylamines with α-chloro-α-phenylthioketones, leading to 1-benzoyl- and 1-pivaloyl-tetrahydroisoquinolines under modified Pictet–Spengler conditions, is described. The synthesis of O-methylvelucryptine employing this transformation as a key step is reported.

  的反应Ñ -tosyl-β-苯乙胺与α氯代-α-phenylthioketones，改性的Pictet-格勒条件下导致1苯甲酰基和1-新戊酰四氢异喹啉，进行说明。报道了使用该转化作为关键步骤的O-甲基维隐氨酸的合成。
• Ammonium Chloride‐Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation
  作者：Chunling Blue Lan、Karine Auclair

  DOI：10.1002/ejoc.202101059

  日期：2021.10.7

  Ammonium chloride promotes the selective formation of monosubstituted ureas under microwave irradiation. Most nucleophiles, acid-labile functionalities, and protecting groups are well tolerated in this reaction. By avoiding transition metals and mineral acids, this methodology offers a more sustainable alternative for the synthesis of monosubstituted ureas and their analogs.

  氯化铵在微波辐射下促进单取代脲的选择性形成。大多数亲核试剂、酸不稳定官能团和保护基团在该反应中具有良好的耐受性。通过避免过渡金属和无机酸，该方法为合成单取代脲及其类似物提供了一种更可持续的替代方案。
• Superparamagnetic Fe₃ O₄ Nanoparticles in a Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Primary Carbamates and Monosubstituted Ureas
  作者：Iman Dindarloo Inaloo、Sahar Majnooni、Mohsen Esmaeilpour

  DOI：10.1002/ejoc.201800581

  日期：2018.7.13

  Superparamagnetic Fe3O4 nanoparticles were used to prepare primary carbamates as well as monosubstituted and N,N‐disubstituted ureas. This efficient phosgene‐free process used urea as an eco‐friendly carbonyl source in the presence of a biocompatible deep eutectic solvent (DES) to provide an inexpensive and attractive route that afforded the products in moderate to excellent yields. (MNP = magnetite nanoparticles

  超顺磁性Fe 3 O 4纳米颗粒用于制备氨基甲酸酯以及单取代的和N，N-二取代的脲。这种有效的无光气工艺在生物相容性深共熔溶剂（DES）的存在下将尿素用作环保的羰基来源，从而提供了一种廉价且有吸引力的途径，使产品收率适中至优异。（MNP =磁铁矿纳米颗粒，Ch =胆碱）
• Modification of biologically active amides and amines with fluorine-containing heterocycles 1. Novel fluorine-containing heterocyclic derivatives of streptocide
  作者：V. B. Sokolov、A. Yu. Aksinenko、T. A. Epishina、T. V. Goreva、I. V. Martynov

  DOI：10.1007/s11172-010-0061-z

  日期：2010.1

  known antimicrobial drug, streptocide, with fluorine-containing five-membered heterocycles is proposed. The reaction of the generated in situ methyl 2-[4-(N-acetylamino)phenylsulfonyl]imino-3,3,3-trifluoropropionate with 1,3-C,N- or 1,3-N,N-binucleophiles and subsequent hydrolysis of the resulting products furnished different novel fluorine-containing heterocyclic derivatives of streptocide, including fused

  提出了一种用含氟五元杂环修饰已知抗微生物药物杀链菌剂的方法。生成的 2-[4-(N-乙酰氨基) 苯基磺酰基]亚氨基-3,3,3-三氟丙酸甲酯与 1,3-C,N- 或 1,3-N,N- 亲双核试剂的原位反应以及随后的反应所得产物的水解提供了不同的新型链霉杀灭剂含氟杂环衍生物，包括稠合杂环。
• Dopamine quinone chemistry: a study of the influence of amide, amidine and guanidine substituents [-NH-CX-Y] on the mode of reaction
  作者：Edward J. Land、Almudena Perona、Christopher A. Ramsden、Patrick A. Riley

  DOI：10.1039/b819367c

  日期：——

  The influence of N-substituents on the mode of reaction of ortho-quinones generated by oxidation of N-substituted dopamine derivatives 8 has been studied. Ortho-quinones with amide, urea or guanidine side chains are relatively stable, with evidence of rearrangement to para-quinomethanes. The N-methylthiourea derivative 11 rapidly cyclises giving a bicyclic product 12. The trichloromethylamidine derivative

  已经研究了N-取代基对由N-取代的多巴胺衍生物8的氧化产生的邻醌的反应方式的影响。邻苯二甲酰胺尿素胍侧链或胍侧链是相对稳定的，具有重排为对喹啉甲烷的证据。所述Ñ -methylthiourea衍生物11迅速cyclises给予双环产物12。三氯甲基am衍生物13也快速环化，但在这种情况下给出螺环衍生物14。相反由其它瞬态形成螺环产物的邻-quinones从多巴胺衍生物衍生的，例如，19，产品14是稳定的并且已经被分离和完全表征。