N-1-[2‐methyl‐3‐oxo‐1,3‐diphenylpropyl] acetamide | 85356-36-1

• 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-[2‐methyl‐3‐oxo‐1,3‐diphenylpropyl] acetamide
• 英文别名: N-1-[(1SR,2RS)-2-methyl-3-oxo-1,3-diphenylpropyl]acetamide；N-((1SR,2RS)-2-methyl-3-oxo-1,3-diphenylpropyl)acetamide；N-(2-methyl-3-oxo-1,3-phenyl-propyl)-acetamide；1-Acetamido-2-methyl-1,3-diphenylpropan-3-one；N-(2-Methyl-3-oxo-1,3-diphenylpropyl)acetamide；N-[(1S,2R)-2-methyl-3-oxo-1,3-diphenylpropyl]acetamide
• CAS: 85356-36-1
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: FXNMGEIJFXKOCQ-DYVFJYSZSA-N

物化性质

• 熔点：
  140 °C
• 沸点：
  500.9±50.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-1-[2‐methyl‐3‐oxo‐1,3‐diphenylpropyl] acetamide 在 二异丁基氢化铝 、 zinc(II) chloride 作用下， 生成 (1R*,2S*,3R*)-3-Acetamido-2-methyl-1,3-diphenyl-1-propanol
  参考文献：
  名称：

  Stereoselective synthesis of 1,3-amino alcohols and 1,3-amino ketones

  摘要：

  Syn,anti-N-Alkyl-1,3-amino alcohols 2 with three chiral centers are synthesized with high stereoselectively by reduction of the corresponding anti-N-acylamino ketones 1 with LiAlH4/TiCl4. The intermediate N-acylamino alcohols 3 can be isolated when DIBALH/ZnCl2 is used instead of the prior reducing system. Cyclic models are proposed to explain the steric course of the reaction in both cases. On the other hand, hydrolysis of tetrahydropyrimidines 8 with 1 N HCl at 25-degrees-C leads to syn-1,3-amino ketones 9 with high stereoselectivity. Several reducing reagents and conditions are tested in the conversion of syn-9 into the subsequent 1,3-amino alcohols. DIBALH/ZnCl2 gives the best results in the last reaction leading to syn,syn-1,3-amino alcohols 10 as practically a single diastereoisomer.

  DOI：

  10.1021/jo00030a033
• 作为产物：
  描述：

  2-Methyl-N1,1,3-triphenylprop-1-ene-1,3-diamine 在 硫酸 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 5.5h， 生成 N-1-[2‐methyl‐3‐oxo‐1,3‐diphenylpropyl] acetamide
  参考文献：
  名称：

  Reduction of 1,3-diimines. A new and general method of synthesis of .gamma.-diamines, .beta.-amino ketones, and derivatives with two and three chiral centers

  摘要：

  DOI：

  10.1021/jo00161a022

文献信息

• One-pot preparation of β-amido ketones/esters in a three-component condensation reaction using magnesium hydrogensulfate as an effective and reusable catalyst
  作者：Hamid Reza Shaterian、Asghar Hosseinian、Majid Ghashang

  DOI：10.1139/v08-013

  日期：2008.5.1

  three-component condensation of an aryl aldehyde, an enolizable ketone or β-keto ester, acetyl chloride, and acetonitrile or benzonitrile in the presence of magnesium hydrogensulfate as an active, recoverable, and reusable green catalyst is described for the synthesis of β-amido ketones/esters at room temperature. The key features of this methodology are simplicity, mild reaction conditions, and high

  在硫酸氢镁作为活性、可回收和可重复使用的绿色催化剂存在下，芳醛、可烯醇化酮或 β-酮酯、乙酰氯和乙腈或苯甲腈的一锅三组分缩合反应被描述用于在室温下合成 β-酰胺酮/酯。该方法的主要特点是简单、反应条件温和、收率高至极好。关键词：多组分反应、硫酸氢镁、多相催化剂、β-酰胺基酮/酯、温和条件。
• One-Pot Multicomponent Synthesis of β-Acetamido Ketones Based on BiCl₃ Generated in situ from the Procatalyst BiOCl and Acetyl Chloride
  作者：Rina Ghosh、Swarupananda Maiti、Arijit Chakraborty

  DOI：10.1055/s-2004-836024

  日期：——

  Aromatic aldehydes react in one pot at room temperature with enolizable ketones and acetonitrile in the presence of acetyl chloride and catalytic amount of BiOCl producing the corresponding β-acetamido ketones in very high to excellent yields. BiCl3 ­generated in situ from BiOCl and acetyl chloride catalyzes the ­multicomponent reaction.

  芳香醛在室温下一锅反应，与可烯醇化的酮和乙腈在醋酸氯和催化量的BiOCl的存在下，产生对应的β-乙酰氨基酮，产率非常高到优异。BiOCl与醋酸氯原位产生的BiCl3催化了多组分反应。
• ZrOCl2·8H2O: an efficient Lewis acid catalyst for the one-pot multicomponent synthesis of β-acetamido ketones
  作者：Rina Ghosh、Swarupananda Maiti、Arijit Chakraborty、Santu Chakraborty、Alok K. Mukherjee

  DOI：10.1016/j.tet.2006.02.037

  日期：2006.4

  Aromatic aldehydes were reacted in one-pot with enolisable ketones, acetonitrile and acetyl chloride at ambient temperature in the presence of ZrOCl2·8H2O to furnish the corresponding β-acetamido ketones in very good to excellent yields. X-ray crystallographic analysis of one anti-β-acetamido ketone exhibited a two-dimensional supramolecular framework by a combination of N–H⋯O, C–H⋯O and C–H⋯π (arene)

  在环境温度下，在ZrOCl 2 ·8H 2 O的存在下，使芳香醛与可固化的酮，乙腈和乙酰氯一锅反应，以非常好的至极好的收率提供相应的β-乙酰胺基酮。一种抗-β-乙酰氨基酮的X射线晶体学分析显示了N–H⋯O，C–H⋯O和C–H⋯π（芳烃）氢键的组合，具有二维超分子构架。
• Supported L-pyrrolidine-2-carboxylic acid-4-hydrogen sulphate on silica gel as an economical and efficient catalyst for the one-pot preparation of for the one-pot preparation of β-acetamido ketones via a four-component condensation reaction
  作者：ARASH GHORBANI-CHOGHAMARANI、PARISA ZAMANI

  DOI：10.1007/s12039-013-0538-z

  日期：2014.1

  oxylic acid-4-hydrogen sulphate (supported on silica gel), a green and non-toxic catalyst, is described for the preparation of β-acetamido ketones in good to excellent yields. An efficient multi-component procedure, catalysed by L-pyrrolidine-2-carboxylic acid-4-hydrogen sulphate (supported on silica gel), as green and non-toxic catalyst, has been applied for the preparation of \u03b2-acetamido ketones

  在催化量的L-吡咯烷-2-羧酸-4-硫酸氢盐存在下，高效，一锅，四组分缩合醛，苯乙酮（或苯乙酮），乙酰氯和乙腈（硅胶支撑）描述了一种绿色且无毒的催化剂，用于以良好至极好的收率制备β-乙酰氨基酮。 在绿色和无毒的催化剂下，由L-吡咯烷-2-羧酸-4-硫酸氢盐（载于硅胶上）催化的高效多组分方法已被用于制备\ u03b2-乙酰氨基酮。回流条件。
• Studying catalytic activity of ternary mixed‐metal Keggin H₇SiV₃W₉O₄₀as a versatile acid catalyst for the synthesis of β‐acetamido ketones
  作者：Reza Tayebee、Akbar Pejhan

  DOI：10.1002/aoc.5350

  日期：2020.2

  One‐pot four‐component condensation of an aromatic aldehyde with an enolisable ketone and acetyl chloride is investigated in the presence of H7SiV3W9O40 in acetonitrile. The prepared catalyst was characterized by standard techniques such as XRD, SEM, and FT‐IR to verify the Keggin structure of nanocatalyst. Furthermore, findings revealed a very good catalytic activity for the applied vanadium substituted

  在乙腈中存在H 7 SiV 3 W 9 O 40的情况下，研究了芳香醛与可缩合的酮和乙酰氯的单锅四组分缩合反应。用XRD，SEM和FT-IR等标准技术对制备的催化剂进行表征，以验证纳米催化剂的Keggin结构。此外，发现表明在该酸催化的缩合反应中，所用的钒取代的杂多酸具有非常好的催化活性。比较了一系列Keggin Si和V-取代的杂多酸对β-乙酰氨基-β-（4-氯苯基）苯乙酮的合成，显示出对H 7 SiV 3 W 9 O更好的催化活性。40和H 4 SiW 12 O 40比介电和混合金属Keggin H 4 SiW 9 Mo 3 O 40和H 5 SiW 9 Mo 2 VO 40高。另外，在该催化体系中也证明了硝化剂的作用，并且发现表明与乙腈相比，PhCN的熟练程度较低。此外，丙苯酮作为一种可被α-取代的可酮化酮与一些芳族醛反应，并且检测到反异构体是主要的非对映异构体。因此，H 7 SiV