1,3-diphenyl-3-[N-(2-chlorophenylamino)]propan-1-one | 94864-06-9

• 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: 1,3-diphenyl-3-[N-(2-chlorophenylamino)]propan-1-one
• 英文别名: 3-((2-chlorophenyl)amino)-1,3-diphenylpropan-1-one；β-(2-Chlor-anilino)-β-phenyl-propiophenon；3-(2-chlorophenylamino)-3-phenyl-1-phenylpropan-1-one；3-(2-chloroanilino)-1,3-diphenylpropan-1-one
• CAS: 94864-06-9
• 化学式: C₂₁H₁₈ClNO
• 分子量: 335.833
• InChiKey: AXIKPZCPZPGKJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-diphenyl-3-[N-(2-chlorophenylamino)]propan-1-one 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以64%的产率得到1,3-diphenyl-3-(2-chlorophenylamino)propen-1-one
  参考文献：
  名称：

  New Synthesis ofβ-Anilinochalcones by Regioselective Oxidation ofβ-Anilinodihydrochalcones Using Iodine–DMSO

  摘要：

  beta-Anilinodihydrochalcones readily undergo oxidation alpha to the carbonyl group region in the presence of a catalytic amount of iodine in dimethyl sulfoxide at 130 degrees C in good yield. Oxidation of allyloxy-substituted beta-anilinodihydrochalcones to beta-anilinochalcones is a preferred reaction over deallylation.

  DOI：

  10.1080/00397911.2012.667490
• 作为产物：
  描述：

  苯甲醛 、 苯乙酮 、 邻氯苯胺 在 C₁₁H₁₈N₃O₂⁽¹⁺⁾*C₂F₃O₂^(1-) 作用下， 以 neat (no solvent) 为溶剂， 反应 2.0h， 以95%的产率得到1,3-diphenyl-3-[N-(2-chlorophenylamino)]propan-1-one
  参考文献：
  名称：

  无溶剂条件下离子液体固定化脯氨酸有机催化剂催化的一锅多组分曼尼希反应

  摘要：

  摘要 对于无溶剂条件下使用离子液体固定的脯氨酸有机催化剂的单锅曼尼希反应，已经建立了一种高效，清洁，简便的方法。含有取代的苯乙酮，取代的芳族醛和取代的芳族胺的三种组分在7 mol％离子液体固定的脯氨酸有机催化剂存在下进行曼尼希反应，可在室温下2-3小时内提供β-氨基羰基化合物优异的产量。该方法具有许多优点，例如反应条件温和，反应时间短，催化剂负载率低，多组分方法，无过渡金属和无溶剂合成。 图形摘要

  DOI：

  10.1007/s11164-020-04096-w

文献信息

• Salicylato Titanocene Complexes as Cooperative Organometallic Lewis Acid and Brønsted Acid Catalysts for Three-Component Mannich Reactions
  作者：Ya Wu、Chun Chen、Gai Jia、Xuyang Zhu、Huaming Sun、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1002/chem.201402438

  日期：2014.7.7

  A binary acid system has been developed that features an air‐stable organometallic precursor, titanocene dichloride, and simple organic cooperative Brønsted acids, which allowed for mild and highly efficient Mannich reactions of both aryl and alkyl ketones with excellent yields and satisfactory diastereoselectivity. Mechanistic studies, including 1H NMR titration, X‐ray structure analyses as well as

  已经开发了一种二元酸体系，其特征是具有空气稳定性的有机金属前体，二茂钛二氯化物和简单的有机协作布朗斯台德酸，可实现芳基和烷基酮的温和高效的曼尼希反应，并具有优异的收率和令人满意的非对映选择性。机理研究，包括1 H NMR滴定，X射线结构分析以及催化活性物质的分离，阐明了这种新的二元酸体系的巨大协同作用。
• Hf(OTf)4 as a Highly Potent Catalyst for the Synthesis of Mannich Bases under Solvent-Free Conditions
  作者：Shuai-Bo Han、Jing-Ying Wei、Xiao-Chong Peng、Rong Liu、Shan-Shan Gong、Qi Sun

  DOI：10.3390/molecules25020388

  日期：——

  Hf(OTf)4 was identified as a highly potent catalyst (0.1–0.5 mol%) for three-component Mannich reaction under solvent-free conditions. Hf(OTf)4-catalyzed Mannich reaction exhibited excellent regioselectivity and diastereoselectivity when alkyl ketones were employed as substrates. 1H NMR tracing of the H/D exchange reaction of ketones in MeOH-d4 indicated that Hf(OTf)4 could significantly promote the

  Hf(OTf)4 被确定为在无溶剂条件下进行三组分曼尼希反应的高效催化剂（0.1-0.5 mol%）。当使用烷基酮作为底物时，Hf(OTf)4 催化的曼尼希反应表现出优异的区域选择性和非对映选择性。酮在 MeOH-d4 中的 H/D 交换反应的 1H NMR 示踪表明 Hf(OTf)4 可以显着促进酮-烯醇互变异构化，从而有助于加快反应速率。
• Bi(NO3)3•5H2O: An Efficient and Green Catalyst for Synthesis of 1,5-Benzodiazepines and b-Amino Carbonyl Compounds
  作者：Jaspreet Kaur Rajput、Gagandeep Kaur

  DOI：10.14233/ajchem.2013.14353

  日期：——

  Bismuth nitrate pentahydrate is found to be an efficient catalyst for the synthesis of 1,5-benzodiazepines and b-amino carbonyl compounds using condensation of o-phenylenediamine with ketones and one pot three component Mannich reaction, respectively under solvent free conditions at room temperature. This method offers a simple, solvent free, room temperature, environment friendly synthesis of 1,5-benzodiazepines and b-amino carbonyl compounds. The products are isolated by column chromatography and recrystallization, respectively and were characterized by their melting point, IR and 1H NMR spectroscopy.

  五水合硝酸铋被发现是一种高效的催化剂，可在无溶剂、室温条件下分别通过邻苯二胺与酮的缩合反应以及一锅法三组分曼尼希反应合成1,5-苯二氮杂卓和β-氨基羰基化合物。这种方法提供了一种简单、无溶剂、室温、环境友好的合成1,5-苯二氮杂卓和β-氨基羰基化合物的方式。产物分别通过柱层析和重结晶进行分离，并利用熔点、红外光谱和核磁共振氢谱进行表征。
• Highly Efficient Fe(HSO₄)₃-Catalyzed One-Pot Mannich-Type Reactions: Three Component Synthesis of β-amino Carbonyl Compounds
  作者：Hossein Eshghi、Afsaneh Alipour、Saman Damavandi

  DOI：10.1080/15533174.2011.555858

  日期：2011.4.11

  Fe(HSO4)3-catalyzed three-component one-pot Mannich reaction of acetophenone with different aromatic aldehydes and aromatic amines in ethanol at ambient temperature afforded the corresponding -aminocarbonyl compounds in very good to excellent yields. Short reaction time, excellent yield, easy work-up procedure, applicability of using various amines and aldehydes, capability of conversion of ortho-substituted

  在环境温度下，Fe（HSO 4）3催化苯乙酮与不同的芳族醛和芳族胺的三组分一锅曼尼希反应在乙醇中以非常好的产率获得了相应的-氨基羰基化合物。反应时间短，产率高，后处理容易，使用各种胺和醛的适用性，将邻位取代的芳族胺以令人满意的产率转化为相应的曼尼希碱的能力以及最终催化剂的高可重复使用性显示出这项研究。
• Solvent strategy for unleashing the Lewis acidity of titanocene dichloride for rapid Mannich reactions
  作者：Ya Wu、Xiu Wang、Yanlong Luo、Jing Wang、Yajun Jian、Huaming Sun、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1039/c5ra27094d

  日期：——

  The remarkable activation effect of alcohol solvent on kinetically inert titanocene dichloride was found to promote rapid three-component Mannich reactions. NMR and ESI-MS analyses as well as a control experiment of catalytic active species elucidated that the coordination of MeOH to the titanocene moiety unleashed the Lewis acid [Cp2Ti(OMe)2] and Brønsted acid HCl, which led to the enhanced catalytic

  发现醇溶剂对动力学惰性二茂钛二氯化物的显着活化作用促进了快速的三组分曼尼希反应。NMR和ESI-MS分析以及催化活性物种的对照实验表明，MeOH与二茂钛部分的配位释放出路易斯酸[Cp 2 Ti（OMe）2 ]和布朗斯台德HCl，从而增强了催化作用Cp 2 TiCl 2的活性。