2-[bis(2-methoxyethyl)aminomethyl]-4-chlorophenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[bis(2-methoxyethyl)aminomethyl]-4-chlorophenol
• 英文别名: 2-[[Bis(2-methoxyethyl)amino]methyl]-4-chlorophenol；2-[[bis(2-methoxyethyl)amino]methyl]-4-chlorophenol
• 化学式: C₁₃H₂₀ClNO₃
• mdl: MFCD26205469
• 分子量: 273.76
• InChiKey: YVQURMUHLLVQKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[bis(2-methoxyethyl)aminomethyl]-4-chlorophenol 、 zinc(II) iodide 以 甲醇 为溶剂， 反应 2.0h， 以70%的产率得到
  参考文献：
  名称：

  Phosphatase models: Synthesis, structure and catalytic activity of zinc complexes derived from a phenolic Mannich-base ligand

  摘要：

  A series of dinuclear [Zn-2(L1)(2)X-2] (1-3) and mononuclear [Zn(HL2)X-2] complexes (4-6), (X = Cl, Br, I) were synthesised from two Mannich-base compartmental ligands, namely [bis(2-methoxyethyl)aminomethyl]-4-chlorophenol (HL1) and 2,6-bis[bis(2-methoxyethyl]aminomethyl]-4-chlorophenol (HL2), respectively. They were characterised by routine physicochemical techniques (CHN, UV, IR, ESI-MS and NMR) and complex 2-5 was further structurally characterised by single crystal X-ray analysis where the Zn center dot center dot center dot Zn bond-distance is 3.10-3.12 angstrom. All the quintessential complexes exhibit excellent phosphatase activity and the experimental first order rate constant values (k(cat)) for the hydrolysis of 4-nitrophenyl phosphate ester (PNPP) reaction in methanol are in the range from 1.05 to 214 s(-1) at 25 degrees C evaluated by monitoring spectrophotometrically the gradual release of p-nitrophenolate (lambda(max) = 427 nm, epsilon = 18500 M-1 cm(-1)). The coordinated X halides affect the phosphatase activity in the order Br > Cl > 1 (in dinuclear complexes) and Cl > Br > I (in mononuclear) and the trend in the two cases has been well recognised to be due to a different rate determining step. Moreover the influence of chloro atom in para-position of the phenol ring and the role of solvent have been rationalised by comparing the kinetic parameters with those obtained for the corresponding methyl analogues having reasonably close structural resemblance as reported by Sanyal et al. (2014). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.05.013
• 作为产物：
  描述：

  聚合甲醛 、 双(2-甲氧基乙基)胺 、 对氯苯酚 以 乙醇 为溶剂， 反应 9.0h， 以80%的产率得到2-[bis(2-methoxyethyl)aminomethyl]-4-chlorophenol
  参考文献：
  名称：

  Catecholase activity of Mannich-based dinuclear Cu^II complexes with theoretical modeling: new insight into the solvent role in the catalytic cycle

  摘要：

  采用Mannich基配体的二铜（II）配合物，通过实验和理论相结合的方法探究了儿茶酚酶活性。

  DOI：

  10.1039/c6nj00105j

文献信息

• Phosphatase models: Synthesis, structure and catalytic activity of zinc complexes derived from a phenolic Mannich-base ligand
  作者：Ria Sanyal、Prateeti Chakraborty、Ennio Zangrando、Debasis Das

  DOI：10.1016/j.poly.2015.05.013

  日期：2015.9

  A series of dinuclear [Zn-2(L1)(2)X-2] (1-3) and mononuclear [Zn(HL2)X-2] complexes (4-6), (X = Cl, Br, I) were synthesised from two Mannich-base compartmental ligands, namely [bis(2-methoxyethyl)aminomethyl]-4-chlorophenol (HL1) and 2,6-bis[bis(2-methoxyethyl]aminomethyl]-4-chlorophenol (HL2), respectively. They were characterised by routine physicochemical techniques (CHN, UV, IR, ESI-MS and NMR) and complex 2-5 was further structurally characterised by single crystal X-ray analysis where the Zn center dot center dot center dot Zn bond-distance is 3.10-3.12 angstrom. All the quintessential complexes exhibit excellent phosphatase activity and the experimental first order rate constant values (k(cat)) for the hydrolysis of 4-nitrophenyl phosphate ester (PNPP) reaction in methanol are in the range from 1.05 to 214 s(-1) at 25 degrees C evaluated by monitoring spectrophotometrically the gradual release of p-nitrophenolate (lambda(max) = 427 nm, epsilon = 18500 M-1 cm(-1)). The coordinated X halides affect the phosphatase activity in the order Br > Cl > 1 (in dinuclear complexes) and Cl > Br > I (in mononuclear) and the trend in the two cases has been well recognised to be due to a different rate determining step. Moreover the influence of chloro atom in para-position of the phenol ring and the role of solvent have been rationalised by comparing the kinetic parameters with those obtained for the corresponding methyl analogues having reasonably close structural resemblance as reported by Sanyal et al. (2014). (C) 2015 Elsevier Ltd. All rights reserved.
• Catecholase activity of Mannich-based dinuclear Cu^II complexes with theoretical modeling: new insight into the solvent role in the catalytic cycle
  作者：Ria Sanyal、Priyanka Kundu、Elena Rychagova、Grigory Zhigulin、Sergey Ketkov、Bipinbihari Ghosh、Shyamal Kumar Chattopadhyay、Ennio Zangrando、Debasis Das

  DOI：10.1039/c6nj00105j

  日期：——

  Catecholase activity has been explored by combined experimental and theoretical approaches using di-copper(ii) complexes of Mannich-base ligands.

  采用Mannich基配体的二铜（II）配合物，通过实验和理论相结合的方法探究了儿茶酚酶活性。