3-((4-chlorophenyl)(piperidin-1-yl)methyl)-4-hydroxy-2H-chromen-2-one | 1330776-86-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-((4-chlorophenyl)(piperidin-1-yl)methyl)-4-hydroxy-2H-chromen-2-one
• 英文别名: 3-[(4-chlorophenyl)(piperidin-1-yl)methyl]-4-hydroxy-chromen-2-one；3-[(4-Chlorophenyl)-piperidin-1-ylmethyl]-4-hydroxychromen-2-one；3-[(4-chlorophenyl)-piperidin-1-ylmethyl]-4-hydroxychromen-2-one
• CAS: 1330776-86-7
• 化学式: C₂₁H₂₀ClNO₃
• 分子量: 369.848
• InChiKey: IFYPAVMMBLCADK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  哌啶 、 4-羟基香豆素 、 4-氯苯甲醛 在 magnetic sulfated zirconia nanocatalyst 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以95%的产率得到3-((4-chlorophenyl)(piperidin-1-yl)methyl)-4-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  Fe3O4 @ ZrO2 / SO42-：一种可回收的磁性多相纳米催化剂，用于通过曼尼希反应合成β-氨基羰基衍生物和苄基氨基香豆素衍生物

  摘要：

  在当前的工作中，我们开发了一种有效的方案，用于通过Mannich型反应以高收率合成β-氨基羰基化合物和合成苄基氨基香豆素衍生物。Fe 3 O 4 @ZrO 2 / SO 4 2‐将其用作曼尼希反应的有效多相纳米催化剂。本研究分为两个部分。在第一部分中，在无溶剂条件下合成了β-氨基羰基衍生物。在另一部分中，在室温下合成苄氨基香豆素化合物。本方法具有许多优点，例如反应时间短，成本低，易于后处理，反应条件温和，收率高，催化剂的回收率和可重复使用性好，而活性没有明显损失。

  DOI：

  10.1002/aoc.4147

文献信息

• An efficient non-ionic surfactant catalyzed multicomponent synthesis of novel benzylamino coumarin derivative via Mannich type reaction in aqueous media
  作者：Atul Kumar、Maneesh Kumar Gupta、Mukesh Kumar

  DOI：10.1016/j.tetlet.2011.06.040

  日期：2011.8

  An efficient non-ionic surfactant catalyzed multicomponent synthesis of novel benzylamino coumarin derivatives has been developed from secondary amines, aromatic aldehyde, and 4-hydroxy coumarin via Mannich type reaction in aqueous media. In this Mannich type reaction, surfactant forms stable colloidal medium to stabilize iminium ion which undergoes nucleophilic addition of 4-hydroxy coumarin to give

  已经通过仲胺，芳族醛和4-羟基香豆素在水介质中通过曼尼希型反应开发了一种有效的非离子表面活性剂催化的多组分合成新型苄基氨基香豆素衍生物的方法。在该曼尼希型反应中，表面活性剂形成稳定的胶体介质以稳定亚胺离子，该亚胺离子经过亲核加成4-羟基香豆素以非常好的收率得到苄基氨基香豆素。
• Catalyst-Free, One-Pot, Expeditious Synthesis of Aminoalkylnaphthols at Room Temperature
  作者：Chhanda Mukhopadhyay、Sunil Rana、Ray J. Butcher

  DOI：10.1080/00397911.2011.575524

  日期：2012.10.15

  Aminoalkylnaphthols possess several biological and catalytic activities. A methodology has been developed for the multicomponent one-pot synthesis of aminoalkylnaphthols in dichloromethane under catalyst-free conditions at room temperature. The present approach possesses several advantages such as excellent yields, quick reaction time, mild reaction conditions, and very easy purification processes. Thirteen new compounds in addition to six known compounds have been synthesized by this methodology.
• One-pot three-component synthesis of 3-(α-aminobenzyl)-4-hydroxycoumarin derivatives using nanocrystalline TiO2 as reusable catalyst
  作者：J. N. Sangshetti、F. A. K. Khan、C. S. Kute、Z. Zaheer、R. Z. Ahmed

  DOI：10.1134/s107042801501011x

  日期：2015.1

  An efficient nanocrystalline TiO2-catalyzed one-pot synthesis of 3-[(piperidin-1-yl)phenylmethyl]- and 3-[(morpholin-4-yl)phenylmethyl]-4-hydroxycoumarins has been developed via three-component Mannich type condensation of 4-hydroxycoumarin with aromatic aldehydes and secondary amines (piperidine or morpholine) in ethanol at room temperature. The catalyst can be easily recovered and reused with almost the same catalytic activity. The proposed method is advantageous due to its simplicity, short reaction time, catalyst reusability, good to excellent yield, and clean and easy work-up.
• Fe ₃ O ₄ @ZrO ₂ /SO ₄ ^2‐ : A recyclable magnetic heterogeneous nanocatalyst for synthesis of β‐amino carbonyl derivatives and synthesis of benzylamino coumarin derivatives through Mannich reaction
  作者：Hossein Ghafuri、Behnaz Ghorbani、Afsaneh Rashidizadeh、Majid Talebi、Mahdi Roshani

  DOI：10.1002/aoc.4147

  日期：2018.3

  developed an effective protocol for the synthesis of β‐amino carbonyl compounds and synthesis of benzylamino coumarin derivatives through Mannich type reaction in high yields. Fe3O4@ZrO2/SO42‐ was employed as an effective heterogeneous nanocatalyst for the Mannich reaction. This research consists of two sections. In first section, β‐amino carbonyl derivatives were synthesized under solvent‐free condition

  在当前的工作中，我们开发了一种有效的方案，用于通过Mannich型反应以高收率合成β-氨基羰基化合物和合成苄基氨基香豆素衍生物。Fe 3 O 4 @ZrO 2 / SO 4 2‐将其用作曼尼希反应的有效多相纳米催化剂。本研究分为两个部分。在第一部分中，在无溶剂条件下合成了β-氨基羰基衍生物。在另一部分中，在室温下合成苄氨基香豆素化合物。本方法具有许多优点，例如反应时间短，成本低，易于后处理，反应条件温和，收率高，催化剂的回收率和可重复使用性好，而活性没有明显损失。