N-(1,3-bis(4-methoxyphenyl)-3-oxopropyl)acetamide | 215813-64-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-(1,3-bis(4-methoxyphenyl)-3-oxopropyl)acetamide
• 英文别名: N-(1,3-bis(4-methoxyphenyl)-3-oxo-1-propyl)acetamide；N-[1,3-bis(4-methoxyphenyl)-3-oxopropyl]acetamide
• CAS: 215813-64-2
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: RHFOVMBAGQROIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(1,3-bis(4-methoxyphenyl)-3-oxopropyl)acetamide 在 盐酸羟胺 作用下， 以 吡啶 为溶剂， 反应 3.0h， 以80%的产率得到N-[3-[(E)-Hydroxyimino]-1,3-bis-(4-methoxy-phenyl)-propyl]-acetamide
  参考文献：
  名称：

  1,3-Diphenylpropane-1,3-diamines XII [1]. A Novel Approach to Stereodefined Oximes and Oxime Ethers of Monothioketalized 1,3-Diketones and their Conversion to 3-Aminooximes

  摘要：

  Mono-O,O- and mono-S,S-ketals of 1,3-diphenylpropane-1,3-diones react with hydroxylamine hydrochloride and O-methylhydroxylamine hydrochloride affording mixtures of (E/Z) isomers which are hard to separate or an even unseparable. Isomerically pure oximes and O-methyloximes, however, are obtained either from 2-lithiated 1,3-dithianes and alpha-halogeno-oximes and alpha-halogeno-oxime ethers, resp., or from lithiated oxime ethers and dithienium salts. Reduction, acetylation, hydrolysis of the ketal increment, and oximation afford 3-amino-oximes which are precursors of 1,3-diphenylpropane-1,3-diamines.

  DOI：

  10.1007/pl00013502
• 作为产物：
  描述：

  (E/Z)-2-[2-(4-methoxyphenyl)-1,3-dithiolan-2-yl]-1-(4-methoxyphenyl)ethanone O-methyloxime 在 吡啶 、 硼烷四氢呋喃络合物 、 chloroamine-T 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 64.17h， 生成 N-(1,3-bis(4-methoxyphenyl)-3-oxopropyl)acetamide
  参考文献：
  名称：

  1,3-Diphenylpropane-1,3-diamines XII [1]. A Novel Approach to Stereodefined Oximes and Oxime Ethers of Monothioketalized 1,3-Diketones and their Conversion to 3-Aminooximes

  摘要：

  Mono-O,O- and mono-S,S-ketals of 1,3-diphenylpropane-1,3-diones react with hydroxylamine hydrochloride and O-methylhydroxylamine hydrochloride affording mixtures of (E/Z) isomers which are hard to separate or an even unseparable. Isomerically pure oximes and O-methyloximes, however, are obtained either from 2-lithiated 1,3-dithianes and alpha-halogeno-oximes and alpha-halogeno-oxime ethers, resp., or from lithiated oxime ethers and dithienium salts. Reduction, acetylation, hydrolysis of the ketal increment, and oximation afford 3-amino-oximes which are precursors of 1,3-diphenylpropane-1,3-diamines.

  DOI：

  10.1007/pl00013502

文献信息

• Ionic liquid triethylamine-bonded sulfonic acid {[Et3N–SO3H]Cl} as a novel, highly efficient and homogeneous catalyst for the synthesis of β-acetamido ketones, 1,8-dioxo-octahydroxanthenes and 14-aryl-14H-dibenzo[a,j]xanthenes
  作者：Abdolkarim Zare、Ahmad Reza Moosavi-Zare、Maria Merajoddin、Mohammad Ali Zolfigol、Tahereh Hekmat-Zadeh、Alireza Hasaninejad、Ardeshir Khazaei、Mohammad Mokhlesi、Vahid Khakyzadeh、Fatemeh Derakhshan-Panah、Mohammad Hassan Beyzavi、Esmael Rostami、Azam Arghoon、Razieh Roohandeh

  DOI：10.1016/j.molliq.2011.12.012

  日期：2012.3

  the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes from β-naphthol (2 equiv.) and aldehydes (1 equiv.) in harsh conditions (120 °C) in the absence of solvent. High yields, relatively short reaction times, efficiency, generality, clean process, simple methodology, low cost, easy work-up, ease of preparation and regeneration of the catalyst and green conditions (in the synthesis of the xanthene derivatives)

  在这项工作中，新型布朗斯台德酸性离子液体三乙胺键合磺酸[Et 3 N–SO 3 H] Cl，N，N -N-二乙基-N-磺基硫代氯化铵}作为均相和绿色催化剂的效率，通用性和适用性研究了各种条件下的有机转化。在此，在[Et 3 N–SO 3H] Cl的研究：（i）由苯乙酮，醛，乙腈和乙酰氯在溶液中和在极温和的条件下（室温）合成β-乙酰氨基酮，（ii）制备1,8-二氧-八氢氧杂蒽在中等温度（80°C）下于无溶剂条件下由二甲酮（5,5-二甲基-1,3-环己二酮）（2当量）和醛（1当量）合成，以及（iii）14-芳基-14 H-二苯并[ a，jβ-萘酚（2当量）和醛（1当量）中的]黄嘌呤在苛刻条件下（120°C）且无溶剂存在。高收率，相对短的反应时间，效率，通用性，清洁的方法，简单的方法，低成本，后处理，催化剂的易于制备和再生以及绿色条件（在an吨衍生物的合成中）是该方法的优点。 [Et 3 N–SO
• Efficient Synthesis of β-Acetamido Ketones and Esters Using Aluminum Chloride as an Inexpensive and Green Catalyst
  作者：Zolfigol Mohammad Ali、Khazaei Ardeshir、Mokhlesi Mohammad、Zare Abdolkarim、Safaiee Maliheh、Derakhshan-Panah Fatemeh、Keypour Hassan、Ali Dehghani-Firouzabadi Ahmad、Merajoddin Maria

  DOI：10.1002/cjoc.201180460

  日期：2012.2

  Aluminum chloride (AlCl3) efficiently catalyzes one‐pot multicomponent condensation of enolizable ketones or alkyl acetoacetates with aldehydes, acetonitrile and acetyl chloride to afford β‐acetamido ketone or ester derivatives in high to excellent yields and in relatively short reaction times. Moreover, by this synthetic method, some novel β‐acetamido ketones and esters (i.e. one complex structure)

  氯化铝（AlCl 3）有效地催化可烯化的酮或乙酰乙酸烷基酯与醛，乙腈和乙酰氯的单锅多组分缩合反应，从而以高产率，优异的产率和相对较短的反应时间提供β-乙酰胺基酮或酯衍生物。此外，通过这种合成方法，制备了一些新型的β-乙酰氨基酮和酯（即一个复杂的结构）。
• Solid-supported sulfonic acid-containing catalysts efficiently promoted one-pot multi-component synthesis of β-acetamido carbonyl compounds
  作者：MOHAMMAD ALI ZOLFIGOL、ARDESHIR KHAZAEI、ABDOLKARIM ZARE、MOHAMMAD MOKHLESI、TAHEREH HEKMAT-ZADEH、ALIREZA HASANINEJAD、FATEMEH DERAKHSHAN-PANAH、AHMAD REZA MOOSAVI-ZARE、HASSAN KEYPOUR、AHMAD ALI DEHGHANI-FIROUZABADI、MARIA MERAJODDIN

  DOI：10.1007/s12039-011-0210-4

  日期：2012.3

  glycol-6000 (PEG-OSO3H) efficiently catalysed one-pot multi-component condensation of enolizable ketones or alkyl acetoacetates with arylaldehydes, acetonitrile and acetyl chloride to afford the corresponding β-acetamido ketone or ester derivatives in high to excellent yields and in relatively short reaction times. Moreover, in this work, some novel β-acetamido carbonyl compounds (i.e., one complex structure)

  二氧化硅官能化的磺酸（SFSA）和硫酸改性的聚乙二醇-6000（PEG-OSO 3 H）有效催化可烯化的酮或乙酰乙酸烷基酯与芳醛，乙腈和乙酰氯的一锅多组分缩合反应，得到相应的β-乙酰氨基酮或酯衍生物的收率高至优异，而且反应时间相对较短。而且，在这项工作中，合成了一些新颖的β-乙酰氨基羰基化合物（即一个复杂的结构）。 二氧化硅官能化的磺酸（SFSA）和硫酸改性的聚乙二醇-6000（PEG-OSO 3 H）可有效催化一锅多组分合成β-乙酰胺基酮或酯衍生物，且收率高，反应时间短。
• An Efficient and Simple One-Pot Synthesis of ?-Acetamido Ketones Catalyzed by Ytterbium Triflate in Ionic Liquid
  作者：Anil Kumar、M. Sudershan Rao、Israr Ahmad、Bharti Khungar

  DOI：10.1071/ch08557

  日期：——

  Ytterbium triflate immobilized in the ionic liquid [bmim][BF4] catalyzes the three-component coupling of aromatic aldehydes, enolizable ketones, and acetonitrile in the presence of acetyl chloride at room temperature to afford β-acetamido ketones in good yields. The catalyst can be recovered and recycled for subsequent reactions without any appreciable loss of efficiency.

  固定在离子液体[bmim] [BF 4 ]中的三氟乙磺酸s在室温下，在乙酰氯的存在下，催化芳香醛，可烯化的酮和乙腈的三组分偶联，从而以高收率提供β-乙酰胺基酮。催化剂可以回收并循环用于随后的反应，而没有任何明显的效率损失。
• Pyrazinium Di(hydrogen sulfate) as a Novel, Highly Efficient and Homogeneous Catalyst for the Condensation of Enolizable Ketones with Aldehydes, Acetonitrile and Acetyl Chloride
  作者：Ardeshir Khazaei、Mohammad Ali Zolfigol、Mohammad Mokhlesi、Abdolkarim Zare、Fatemeh Derakhshan-Panah、Maria Merajoddin、Hassan Keypour、Ahmad Ali Dehghani-Firouzabadi

  DOI：10.1002/jccs.201100383

  日期：2012.2

  the synthesis of β‐acetamido ketone or ester derivatives in the presence of pyrazinium di(hydrogen sulfate) Py(OSO3H)2} as a novel, green and homogeneous solid acid catalyst at room temperature is described. One‐pot multi‐component condensation of enolizable ketones or alkyl acetoacetates with aldehydes, acetonitrile and acetyl chloride affords the title compounds in high to excellent yields and in

  描述了一种在吡嗪鎓二（硫酸氢盐）Py（OSO 3 H）2 }存在下，在室温下合成β-乙酰氨基酮或酯衍生物的高效方法，它是一种新颖，绿色且均质的固体酸催化剂。可烯化的酮或乙酰乙酸烷基酯与醛，乙腈和乙酰氯的一锅多组分缩合反应可在较短的反应时间内以高到极好的收率得到标题化合物。在这项工作中，还研究了我们最近报道的固体酸催化剂糖精磺酸（Sa-SO 3 H）在合成β-乙酰氨基酮/酯中的效率。此外，在这项研究中，制备了一些新的β-乙酰氨基酮和酯（即一种复杂的结构）。