2-(3,4-dimethoxyphenyl)-4'-methoxyacetophenone | 4927-53-1

• 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)-4'-methoxyacetophenone
• 英文别名: 3,4-dimethoxybenzyl 4-methoxyphenyl ketone；2-(3,4-Dimethoxyphenyl)-1-(4-methoxyphenyl)ethanon；2-(3,4-dimethoxyphenyl)-1-(4-methoxyphenyl)ethanone；1'-(3,4-dimethoxyphenyl)-2'-(4''-methoxyphenyl)ethan-2'-one；2-(3,4-dimethoxyphenyl)-1-(4-methoxyphenyl)ethan-1-one；3',4,4'-Trimethoxy-desoxybenzoin；4,3',4'-Trimethoxy-desoxybenzoin；4,3',4'-trimethoxy-deoxybenzoin
• CAS: 4927-53-1
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: UOIPJLJDLUDENQ-UHFFFAOYSA-N

物化性质

• 熔点：
  138 °C
• 沸点：
  439.7±35.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxyphenyl)-4'-methoxyacetophenone 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 2'-(ethoxycarbonyl)-4,3',4'-trimethoxydeoxybenzoin
  参考文献：
  名称：

  Influence of alkoxyalkyl substituents in the regioselective lithiation of the benzene ring

  摘要：

  DOI：

  10.1021/jo00169a007
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酸 在 aluminum (III) chloride 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-(3,4-dimethoxyphenyl)-4'-methoxyacetophenone
  参考文献：
  名称：

  复杂的多杂环和 Pileamartine A 通过 Aza-Heck 触发的芳基 C-H 官能化级联的立体化学重新分配

  摘要：

  结构复杂的苯并和螺融合的 N-多杂环可以通过分子内 Pd(0)-催化的烯烃 1,2-氨基芳基化反应获得。该方法使用N -（五氟苯甲酰氧基）氨基甲酸酯作为起始基序，这允许在芳烃组分的 C-H 钯化之前进行 aza-Heck 型烯烃氨基化。这种化学反应在复杂生物碱 (+)-pileamartine A 的首次全合成中得到了展示，这导致了其绝对立体化学的重新分配。

  DOI：

  10.1021/jacs.1c08615

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。

• Further studies on the application of vinylogous amides and β-halovinylaldehydes to the regiospecific synthesis of unsymmetrical, polyfunctionalized 2,3,4- and 1,2,3,4- substituted pyrroles
  作者：John T. Gupton、Alex Shimozono、Evan Crawford、Joe Ortolani、Evan Clark、Matt Mahoney、Campbell Heese、Jeffrey Noble、Carlos Perez Mandry、Rene Kanters、Raymond N. Dominey、Emma W. Goldman、James A. Sikorski、Daniel C. Fisher

  DOI：10.1016/j.tet.2018.04.017

  日期：2018.5

  Highly functionalized pyrroles with appropriate regiochemical functionality represent an important class of marine natural products and potential drug candidates. We describe herein a detailed study of the reaction of α-aminoacid esters with vinylogous amides and also β-halovinylaldehydes for the regiospecific synthesis of 2,3,4-trisubstituted and 1,2,3,4-tetrasubstituted pyrroles. Since the vinylogous

  具有适当区域化学功能的高度官能化的吡咯代表了海洋天然产物和潜在候选药物的重要类别。我们在此描述了α-氨基酸酯与乙烯基酰胺和β-卤代甲醛醛的反应的详细研究，用于2,3,4-三取代和1,2,3,4-四取代的吡咯的区域特异性合成。由于乙烯基酰胺和β-卤代乙醛是易于获得的前体，因此通过这种方法可以快速获得各种不对称取代的吡咯。
• Synthesis of Benzo[<i>b</i>]furans by Intramolecular C–O Bond Formation Using Iron and Copper Catalysis
  作者：Martyn C. Henry、Andrew Sutherland

  DOI：10.1021/acs.orglett.0c00754

  日期：2020.4.3

  synthesis of benzo[b]furans from 1-aryl- or 1-alkylketones using nonprecious transition metal catalysts have been developed. Regioselective iron(III)-catalyzed halogenation of the aryl ring, followed by iron- or copper-catalyzed O-arylation allowed the synthesis of various structural analogues, including the benzo[b]furan-derived natural products corsifuran C, moracin F, and caleprunin B.

  已经开发出使用非贵金属过渡金属催化剂从1-芳基酮或1-烷基酮合成苯并[ b ]呋喃的一锅法。区域选择性铁(III)催化的芳环卤化，然后是铁或铜催化的O-芳基化，可以合成各种结构类似物，包括苯并[ b ]呋喃衍生的天然产物corsifuran C、moracin F和卡普鲁宁 B.
• BF 3 ·OEt 2 -mediated [1,2]-aryl shift: Synthesis of functionalized α-arylnitriles via the bromination/cyanation/deformylation of substituted deoxybenzoin
  作者：Chieh-Kai Chan、Meng-Yang Chang

  DOI：10.1016/j.tet.2017.07.015

  日期：2017.8

  A new sequential, tandem synthesis of functionalized α-arylnitriles via the bromination/cyanation/deformylation of substituted deoxybenzoin has developed. CuBr2-promoted bromination of substituted deoxybenzoins gives 2-bromo-2-arylacetophenne 3. The cyanation of 3 with sodium cyanide (NaCN) generates epoxynitrile. Then, a treatment of epoxynitrile with BF3·OEt2 results in the formation of functionalized

  通过取代的脱氧安息香素的溴化/氰化/去甲酰基化，开发了一种新的顺序串联的官能化α-芳基腈的合成方法。CuBr 2促进的取代脱氧安息香素的溴化反应生成2-溴-2-芳基乙酰基3。的氰化3用氰化钠（NaCN的）epoxynitrile生成。然后，用BF 3 · OEt 2处理环氧腈导致通过1,2-芳基转移形成官能化的α-芳基腈4。
• Catechol estrogens of the 1,1,2-triphenyl-1-butene type. Relationship between structure, estradiol receptor affinity, estrogenic and antiestrogenic properties, and mammary tumor inhibiting activities
  作者：Martin R. Schneider、Hartwig Ball、Claus D. Schiller

  DOI：10.1021/jm00158a006

  日期：1986.8

  rings, were synthesized. The occurring E and Z isomers were isolated, and their identity was established by 1H NMR spectroscopy. A study on structure-activity relationship was carried out with regard to estradiol receptor affinity in vitro, estrogenic and antiestrogenic properties in the immature mouse, and inhibition of the hormone-dependent MXT mammary tumor of the mouse in vivo. Among the tested compounds

  1,1,2-三苯基丁-1-烯（26-35），在两个芳族化合物中被一个或两个3,4-二乙酰氧基或一个3,4-二乙酰氧基和一个3-或4-乙酰氧基取代环，被合成。分离出现的E和Z异构体，并通过1H NMR光谱确定其身份。进行了结构-活性关系的研究，涉及体外雌二醇受体亲和力，未成熟小鼠的雌激素和抗雌激素特性以及体内抑制小鼠激素依赖性MXT乳腺肿瘤。在测试的化合物中，大多数1,1,1-二取代的1,1,2-三苯基丁-1-烯（29，Z-30，Z，E-31）和（E）-1-（3-乙酰氧基苯基）- 1-苯基-2-（3,4-二乙酰氧基苯基）丁-1-烯（E-35）及其各自的Z异构体（Z-35）发挥抗雌激素特性。化合物Z-30，Z，E-31，Z-35，E-35抑制激素依赖性MXT肿瘤的生长。E-35显示出在治疗过程中最佳的抗肿瘤作用而没有雌激素副作用。