3-[(3-methoxyphenyl)amino]-1,3-diphenylpropan-1-one

• 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: 3-[(3-methoxyphenyl)amino]-1,3-diphenylpropan-1-one
• 英文别名: 3-(3-Methoxyanilino)-1,3-diphenylpropan-1-one
• 化学式: C₂₂H₂₁NO₂
• 分子量: 331.414
• InChiKey: PFPYQGDLTRCQIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(3-methoxyphenyl)amino]-1,3-diphenylpropan-1-one 在 Chiralcel OD-H 作用下， 以 乙醇 、 异丙醇 为溶剂， 生成 3-[(3-methoxyphenyl)amino]-1,3-diphenylpropan-1-one 、 3-[(3-methoxyphenyl)amino]-1,3-diphenylpropan-1-one
  参考文献：
  名称：

  各种基于多糖的手性固定相的HPLC手性分离β-氨基酮的筛选方法

  摘要：

  当苯甲醛与一些伯胺和苯乙酮缩合时，通过Mannich反应合成了九种β-氨基酮。通过使用光谱法鉴定纯化的化合物。这些衍生物的对映体分离采用几种涂覆并固定多糖固定相，即，CHIRALCEL通过高效液相色谱法（HPLC）进行® OD-H，CHIRALCEL ® OD，CHIRALCEL ® OJ，CHIRALPAK ® AD，CHIRALPAK ® IA和CHIRALPAK ® IB使用组成不同的流动相ñ正己烷和乙醇按各种比例混合，或纯乙醇或异丙醇。在等度正相模式下检查了这些手性固定相的保留行为和选择性。结果表明，纤维素衍生物在分离外消旋β-氨基酮方面比直链淀粉衍生物具有更高的对映选择性。手性27：332–338，2015年。 ©2015 Wiley Periodicals，Inc.

  DOI：

  10.1002/chir.22434
• 作为产物：
  描述：

  苯甲醛 在 四丁基溴化铵 作用下， 以 neat (no solvent) 为溶剂， 反应 16.0h， 生成 3-[(3-methoxyphenyl)amino]-1,3-diphenylpropan-1-one
  参考文献：
  名称：

  氧化石墨烯作为催化剂，通过在纯净条件下原位生成迈克尔受体，将一锅顺序进行羟醛偶联/将氮的氮杂-迈克尔加成至查耳酮

  摘要：

  氧化石墨烯（GO）与四正丁基溴化铵（TBAB）结合使用，可在单个反应容器中作为有效的催化剂，用于一锅顺序将羟醛偶联/氮杂-迈克尔加成至查耳酮。苯甲醛和苯乙酮就地偶联生成相应的查耳酮，然后在无溶剂条件下进行氮杂-迈克尔加成反应。该程序避免了贵金属的使用，GO的异质性通过简单过滤催化剂简化了产物的纯化和分离。

  DOI：

  10.1016/j.tetlet.2019.151470

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：ASTRAZENECA AB

  公开号：WO2004011410A1

  公开（公告）日：2004-02-05

  Compounds of formula (I):wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  式(I)的化合物：其中变量基团如定义内；用于抑制11βHSD1。
• Ketones
  申请人：Barton John Peter

  公开号：US20050272036A1

  公开（公告）日：2005-12-08

  Compounds of formula (I): wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  描述了式(I)的化合物：其中变量基团如定义的那样；用于抑制11βHSD1。
• KOZLOV N. S.; KOROTYSHOVA G. P., VESPI AN BSSR. CEP. XIM. N., IZV. AN BSSR. CEP. XIM. N. <VVSK-AK>, 1975, +
  作者：KOZLOV N. S.、 KOROTYSHOVA G. P.

  DOI：——

  日期：——
• KETONES
  申请人：AstraZeneca AB

  公开号：EP1549600A1

  公开（公告）日：2005-07-06
• Efficient Monoalkylation of Anilines with Chalcones using Microwave-Assisted aza-Michael Addition
  作者：Hirokazu Iida、Mitsuki Okawa、Siriwat Leeanansaksiri、Kie Takahashi

  DOI：10.2174/1570178619666220128142833

  日期：2022.8

  The aza-Michael addition is an attractive methodology for synthetic organic chemistry because the resulting β-aminocarbonyl compounds are valuable building blocks for the synthesis of pharmaceutically useful compounds. However, monoalkylation of aniline and its derivatives is quite difficult because anilines are poor nucleophiles compared to monoalkylated ones. Since the publication of pioneering articles in 1986, the development of microwave-assisted organic synthesis has been remarkable. Therefore, we began by investigating the monoalkylation of aniline and its derivatives under microwave irradiation. Because of the ready formation of bisalkylated products, the monoalkylation reaction between anilines and Michael acceptors is quite difficult. To overcome the difficulty, we investigated the effect of microwave irradiation for the alkylation of anilines with chalcones as Michael acceptors. Microwave-assisted aza-Michael addition proceeded smoothly to obtain mainly the monoalkylated Michael adduct. The substitution effects of both chalcone and aniline concerning the yield were also studied. We supposed that dimer formation by two monoalkylated compounds produces a bulky environment around the amino group, which prevents monoalkylated compounds from undergoing a second alkylation. We confirmed a highly efficient and rapid method for preparing monoalkylated anilines using microwave-assisted aza-Michael addition between anilines and chalcones.