3-(N-p-chlorophenylamino)-2-methyl-1,3-diphenyl-1-propanone | 95005-60-0

• 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-(N-p-chlorophenylamino)-2-methyl-1,3-diphenyl-1-propanone
• 英文别名: 2-methyl-1,3-diphenyl-3-(p-chlorophenylamino)-1-propanone；β-(4-Chlor-anilino)-α-methyl-β-phenyl-propiophenon；3-(4-Chloroanilino)-2-methyl-1,3-diphenylpropan-1-one
• CAS: 95005-60-0
• 化学式: C₂₂H₂₀ClNO
• 分子量: 349.86
• InChiKey: IZCRNNXVRLJYHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  170-171 °C
• 沸点：
  526.2±45.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三甲基[(Z)-(1-苯基-1-丙烯基)氧基]硅烷 、 N-亚苄基-4-氯苯胺 在 苯甲醛 、 ytterbium(III) triflate 作用下， 以 various solvent(s) 为溶剂， 以87%的产率得到3-(N-p-chlorophenylamino)-2-methyl-1,3-diphenyl-1-propanone
  参考文献：
  名称：

  Aldehydes vs Aldimines. Unprecedented Reactivity in Their Enolate Addition Reactions

  摘要：

  DOI：

  10.1021/jo962010h

文献信息

• Aldehydes vs Aldimines. Unprecedented Aldimine-Selective Nucleophilic Additions in the Coexistence of Aldehydes Using a Lanthanide Salt as a Lewis Acid Catalyst
  作者：Shū Kobayashi、Satoshi Nagayama

  DOI：10.1021/ja971153y

  日期：1997.10.1

  It is well-recognized that aldimines are less reactive than aldehydes toward nucleophilic additions. In this paper, an unprecedented change in the reactivity is described: preferential reactions of aldimines over aldehydes in nucleophilic additions using a lanthanide salt as a Lewis acid catalyst. In the presence of a catalytic amount of ytterbium triflate (Yb(OTf)3), only aldimines reacted with silyl

  众所周知，醛亚胺对亲核加成的反应性低于醛。在本文中，描述了一种前所未有的反应性变化：在亲核加成中使用镧系元素盐作为路易斯酸催化剂，醛亚胺​​优先于醛反应。在催化量的三氟甲磺酸镱 (Yb(OTf)3) 存在下，只有醛亚胺与甲硅烷基烯醇醚、烯酮甲硅烷基缩醛、烯丙基三丁基锡烷或氰基三甲基硅烷反应，以高产率提供相应的加合物，即使在醛共存的情况下也是如此。13C NMR 分析表明选择性形成醛亚胺-Yb(OTf)3 复合物而不是醛-Yb(OTf)3 复合物。虽然这份报告证明了路易斯酸在有机合成中的有效利用，
• Mannich-type reactions of aromatic aldehydes, anilines, and methyl ketones in fluorous biphase systems created by rare earth (III) perfluorooctane sulfonates catalysts in fluorous media
  作者：Wen-Bin Yi、Chun Cai

  DOI：10.1016/j.jfluchem.2006.07.009

  日期：2006.11

  Rare earth (III) perfluorooctane sulfonates (RE(OPf)3) catalyze the three-component Mannich-type reactions of different ketones with various aromatic aldehydes and aromatic amines in fluorous media to give various β-arylamino ketones in good yields. By simple separation of the fluorous phase containing only catalyst, reaction can be repeated several times.

  稀土（III）全氟辛烷磺酸盐（RE（OPf）3）在氟介质中催化不同酮与各种芳香醛和芳香胺的三组分曼尼希型反应，以高收率得到各种β-芳基氨基酮。通过仅含催化剂的氟相的简单分离，反应可重复数次。
• Three-component carbon–carbon bond-forming reactions catalyzed by a Brønsted acid–surfactant-combined catalyst in water
  作者：Kei Manabe、Yuichiro Mori、Shū Kobayashi

  DOI：10.1016/s0040-4020(01)00081-3

  日期：2001.3

  Reactions of aldehydes, amines, and various nucleophiles such as silyl enolates, ketones, Danishefsky's diene, and allyltribuyltin in water were successfully carried out in the presence of p-dodecylbenzenesulfonic acid (DBSA) as a Bronsted acid-surfactant-combined catalyst. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Mannich-Type Reactions of Aldehydes, Amines, and Ketones in a Colloidal Dispersion System Created by a Brønsted Acid−Surfactant-Combined Catalyst in Water
  作者：Kei Manabe、Shū Kobayashi

  DOI：10.1021/ol991113u

  日期：1999.12.1

  [GRAPHICS]Three-component Mannich-type reactions of aldehydes, amines, and ketones were efficiently catalyzed by dodecylbenzenesulfonic acid at ambient temperature in water to give various beta-amino ketones in good yields. The same reactions proceeded sluggishly in organic solvents.