2-(3,4-dimethoxyphenyl)-1-phenylethanone | 29955-23-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(3,4-dimethoxyphenyl)-1-phenylethanone
• 英文别名: 1-Phenyl-2-(3,4-dimethoxyphenyl)ethanone；3,4-dimethoxydeoxybenzoin；3,4-Dimethoxy-2-phenylacetophenone
• CAS: 29955-23-5
• 化学式: C₁₆H₁₆O₃
• mdl: MFCD12653581
• 分子量: 256.301
• InChiKey: WPVHTWVXVUQLAG-UHFFFAOYSA-N

物化性质

• 熔点：
  61.5-62.5 °C
• 沸点：
  386.8±27.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxyphenyl)-1-phenylethanone 在 甲酸 、 溶剂黄146 、 三氟乙酸 作用下， 反应 4.5h， 生成 2-formyl-6,7-dimethoxy-3-phenyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Application of the Intramolecular α-Amidoalkylation Reaction for the Synthesis of 3- and 1,3-Alkyl(aryl) 2-Formyltetrahydroisoquinolines

  摘要：

  3- and 1,3-Alkyl(aryl) 2-Formyltetrahydroisoquinolines 6 are obtained by the application of the intramolecular is-proportional-to -amidoalkylation reaction from 1-Alkyl(Aryl)-2-Arylethylformamides 2 and aldehydes in acidic medium.

  DOI：

  10.1080/00397919308011269
• 作为产物：
  描述：

  (3,4-二甲氧基苯基)乙酰氯 在 盐酸 、 silver perchlorate 作用下， 以 硝基甲烷 为溶剂， 生成 2-(3,4-dimethoxyphenyl)-1-phenylethanone
  参考文献：
  名称：

  Mezheritskaya, L. V.; Matsovskaya, E. S.; Dorofeenko, G. N., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 174 - 178

  摘要：

  DOI：

文献信息

• α-(4-Tolyl)dopamine, derivatives and analogues; Synthesis and pharmacological screening
  作者：Vladimír Valenta、Jiří Holubek、Emil Svátek、Antonín Dlabač、Marie Bartošová、Miroslav Protiva

  DOI：10.1135/cccc19831447

  日期：——

  The ketone XIII, obtained by Friedel-Crafts reaction of toluene with homoveratroyl chloride, was converted by the Leuckart reaction to the formamido derivative IXb which was used as the starting product for the synthesis of amines IIIb-Vb. Reduction of the ketone XIII gave the alcohol XVI which was treated with hydrogen chloride and afforded the chloro compound XVII. Its substitution reactions with 1-methylpiperazine, 1-(2-hydroxyethyl)piperazine and 1-phenylpiperazine resulted in the piperazines VIb-VIIIb. Acylations of the amine IIIb with acetic anhydride and homoveratroyl chloride gave the amides Xb and XIb which, together with the formamide IXb, were subjected to the Bischler-Napieralski reaction. 3,4-Dihydroisoquinolines XXII-XXIV were obtained and reduced to the 1,2,3,4-tetrahydroisoquinolines XXVb-XXVIIb. Treatment of XXVIIb with formaldehyde afforded the berbine derivative XXVIII. Demethylation of the amine IIIb with hydrobromic acid resulted in the title compound IIIa. Similar demethylations of the dimethoxyamines IVb-VIIIb, XXVb and XXVIb led to the dihydroxyamines IVa-VIIIa, XXVa and XXVIa which are dopamine derivatives. Reaction of Va with benzoyl chloride gave the dibenzoate XXX. The CNS activities of the compounds prepared are of a low degree. Several of them (IIIa-VIa, IIIb-Vb, XXVb) show in higher doses signs of central stimulant action but only for compound IVa an antireserpine effect was proven. The expected anticataleptic activity was found only in a low degree with compound VIIIa; on the contrary, compounds IIIa and XXVa are procataleptogenic. Some compounds (IIIa, IXb, XXVIa, XXVIII) potentiated thiopental. In single cases local anaesthetic, spasmolytic, hypotensive, hypertensive, hypoglycaemic, diuretic and antiarrhythmic effects were observed.

  通过将甲苯与同戊酰氯进行弗里德尔-克拉夫茨反应得到的酮XIII，通过勒克阿尔特反应转化为甲酰胺衍生物IXb，后者用作合成胺IIIb-Vb的起始产品。酮XIII的还原得到醇XVI，经氯化氢处理得到氯化合物XVII。它与1-甲基哌嗪、1-(2-羟基乙基)哌嗪和1-苯基哌嗪的取代反应得到哌嗪VIb-VIIIb。胺IIIb与乙酸酐和同戊酰氯的酰化反应得到酰胺Xb和XIb，与甲酰胺IXb一起进行比施勒-纳皮尔兰斯基反应。得到3,4-二氢异喹啉XXII-XXIV，还原为1,2,3,4-四氢异喹啉XXVb-XXVIIb。用甲醛处理XXVIIb得到具夹竹桃碱衍生物XXVIII。用氢溴酸脱甲基胺IIIb得到标题化合物IIIa。类似地，对二甲氧基胺IVb-VIIIb、XXVb和XXVIb的脱甲基得到二羟基胺IVa-VIIIa、XXVa和XXVIa，它们是多巴胺衍生物。Va与苯甲酰氯反应得到二苯甲酸盐XXX。所制备的化合物的中枢神经系统活性程度较低。其中一些(IIIa-VIa、IIIb-Vb、XXVb)在高剂量下表现出中枢兴奋作用，但只有IVa被证实具有抗多巴胺效应。预期的抗惊厥活性只在VIIIa中以低程度发现；相反，化合物IIIa和XXVa具有致惊厥作用。一些化合物(IIIa、IXb、XXVIa、XXVIII)增强了硫喷妥钠的效果。在个别情况下观察到局麻、解痉、降压、升压、降糖、利尿和抗心律失常作用。

• Substituted (1,2-Diarylethyl)amide Acyl-CoA:Cholesterol Acyltransferase Inhibitors: Effect of Polar Groups on in Vitro and in Vivo Activity
  作者：John W. Clader、Joel G. Berger、Robert E. Burrier、Harry R. Davis、Martin Domalski、Sundeep Dugar、Timothy P. Kogan、Brian Salisbury、Wayne Vaccaro

  DOI：10.1021/jm00010a004

  日期：1995.5

  Substituted (1,2-diarylethyl)amides have been prepared and evaluated for their ability to inhibit microsomal acyl-CoA:cholesterol acyltransferase activity in vitro and to lower hepatic cholesteryl ester content in vivo in a cholesterol-fed hamster. Simple unsubstituted (diarylethyl)amides were potent inhibitors in vitro but showed poor activity in vivo. Introduction of polar groups at specific locations

  已经制备了取代的（1,2-二芳基乙基）酰胺，并评估了它们在体外抑制微粒体酰基辅酶A：胆固醇酰基转移酶活性并降低体内胆固醇喂养的仓鼠体内肝胆固醇酯含量的能力。简单的未取代的（二芳基乙基）酰胺在体外是有效的抑制剂，但在体内却显示出较差的活性。在二芳基乙胺部分的特定位置引入极性基团会降低体外活性，但会增加体内活性。两种作用都高度依赖于结构，表明在每种模型中介导活性的特定相互作用。这些相反作用的优化导致化合物在两种模型中均有效。
• Synthesis and evaluation of N-substituted 2-amino-4,5-diarylpyrimidines as selective adenosine A1 receptor antagonists
  作者：Georgios Alachouzos、Eelke B. Lenselink、Thea Mulder-Krieger、Henk de Vries、Adriaan P. IJzerman、Julien Louvel

  DOI：10.1016/j.ejmech.2016.09.081

  日期：2017.1

  We report the synthesis and biological evaluation of new 2-amino-4,5-diarylpyrimidines as selective antagonists at the adenosine A1 receptor. The scaffold they are based upon is a deaza variation of a previously reported collection of 3-amino-5,6-diaryl-1,2,4-triazines, members of which had a subnanomolar affinity but limited selectivity over the A2A subtype. Initially, similar structure-affinity relationships

  我们报告了腺苷A 1受体作为选择性拮抗剂的新的2-氨基-4,5-二芳基嘧啶的合成和生物学评估。它们所基于的支架是先前报道的3-氨基-5,6-二芳基-1,2,4-三嗪类化合物的重氮变异体，其成员具有亚纳摩尔亲和力，但对A 2A亚型的选择性有限。最初，在5-芳基环上建立相似的结构-亲和性关系，然后重点在于通过在N 2-位上引入取代基，同时保持纳摩尔亲和力，来提高在hA 1 AR处的选择性。具有反式的化合物3z4-羟基环取代基，被鉴定为一种有效的（ķ我（HA 1个AR）= 7.7纳米）和选择性的（ķ我（HA 2A AR）= 1389 nm）的拮抗剂在人腺苷A 1个受体。在A 1和A 2A亚型上进行计算对接，使4-羟基环己基取代基对选择性的影响合理化，与嘧啶5-位上的取代基的性质有关。
• Estrogen receptor modulators
  申请人：——

  公开号：US20030225132A1

  公开（公告）日：2003-12-04

  The present invention relates to compounds and derivatives thereof, their synthesis, and their use as estrogen receptor modulators. The compounds of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, cartilage degeneration, endometriosis, uterine fibroid disease, hot flashes, increased levels of LDL cholesterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muscle cell proliferation, obesity, incontinence, and cancer, in particular of the breast, uterus and prostate.

  本发明涉及化合物及其衍生物，它们的合成以及它们作为雌激素受体调节剂的用途。本发明的化合物是雌激素受体的配体，因此可能对治疗或预防与雌激素功能相关的多种疾病条件有用，包括：骨质疏松、骨折、骨质疏松症、软骨退化、子宫内膜异位症、子宫肌瘤病、潮热、低密度脂蛋白胆固醇水平升高、心血管疾病、认知功能障碍、脑退行性疾病、再狭窄、男性乳房增大、血管平滑肌细胞增殖、肥胖、尿失禁和癌症，尤其是乳腺、子宫和前列腺癌。
• Transition-Metal-Free Intermolecular α-Arylation of Ketones via Enolonium Species
  作者：Shimon Maksymenko、Keshaba N. Parida、Gulab K. Pathe、Atul A. More、Yuriy B. Lipisa、Alex M. Szpilman

  DOI：10.1021/acs.orglett.7b03064

  日期：2017.12.1

  Herein it is shown, for the first time, that enolonium species are powerful electrophiles capable of reacting with aromatic compounds in an intermolecular manner to afford α-arylated ketones. The reaction is compatible with a variety of functional groups, is of wide scope with respect to aromatic compounds and ketone, and even works for polymerization-prone substrates such as substituted pyrroles,

  在此首次表明，en烯是能够以分子间方式与芳族化合物反应以提供α-芳基化酮的强亲电试剂。该反应与多种官能团相容，对于芳族化合物和酮而言具有广泛的范围，甚至适用于易于聚合的底物，例如取代的吡咯，噻吩和呋喃。仅需要1.6至5当量的商品芳族底物。