5-(methylaminomethyl)-25,26,27,28-tetrakis(2-ethoxyethoxy)calix<4>arene | 227197-39-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(methylaminomethyl)-25,26,27,28-tetrakis(2-ethoxyethoxy)calix<4>arene
• 英文别名: N-methyl-1-[25,26,27,28-tetrakis(2-ethoxyethoxy)-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]methanamine
• CAS: 227197-39-9
• 化学式: C₄₆H₆₁NO₈
• 分子量: 755.992
• InChiKey: XGUJJVLEYLYZCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.74
• 重原子数：
  55.0
• 可旋转键数：
  22.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  85.87
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5-(methylaminomethyl)-25,26,27,28-tetrakis(2-ethoxyethoxy)calix<4>arene 在 氯化亚砜 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 37.0h， 生成 5-<((6-N,N-dimethylaminomethyl)pyridin-2-yl-methyl)-N-methylaminomethyl>-25,26,27,28-tetrakis(2-ethoxyethoxy)calix<4>arene
  参考文献：
  名称：

  Dinuclear and Trinuclear Zn(II) Calix[4]arene Complexes as Models for Hydrolytic Metallo-Enzymes. Synthesis and Catalytic Activity in Phosphate Diester Transesterification

  摘要：

  Calix[4]arenes modified with two or three Zn(II)-2,6-bis(aminomethyl)pyridyl groups,. 3-[Zn](2) and (3)[Zn](3), respectively, were investigated as models for dinuclear and trinuclear metallo-enzymes that catalyze the cleavage of phosphate diesters. Under neutral conditions, 0.48 mM of 3-[Zn](2) causes a rate acceleration of 23 000 in the transesterification of the RNA model substrate 2-hydroxyproyl-p-nitrophenyl phosphate (HPNP, 0.19 mM). Comparison with the activities of a mononuclear complex 2-[Zn] and a reference complex lacking the calix[4]arene backbone 1-[Zn] shows that the catalysis is due to cooperative action of the Zn(II) centers and indicates that hydrophobic effects contribute to the catalysis. Saturation kinetics and pH variation studies demonstrate that the high catalytic activity of the flexible complex 3-[Zn](2) originates from a very high substrate binding affinity, affording a Michaelis-Menten complex in which the substrate is converted with a relatively moderate rate. A rigid analogue 4-[Zn](2) exhibits both a lower substrate binding strength and a lower catalytic rate. This demonstrates the importance of a certain flexibility between the cooperating catalytic centers. The trinuclear complex 5-[Zn](3) induces a rate acceleration of 32 000 times, and shows a decreased substrate binding and an increased catalytic rate compared to its dinuclear analogue 3-[Zn](2). In a possible mechanism two Zn(II) ions activate the phosphoryl group and another activates the beta-hydroxyl group of HPNP.

  DOI：

  10.1021/jo982201f
• 作为产物：
  描述：

  5-Formyl-25,26,27,28-tetrakis(2-ethoxyethoxy)calix<4>arene 、 甲胺 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 5-(methylaminomethyl)-25,26,27,28-tetrakis(2-ethoxyethoxy)calix<4>arene
  参考文献：
  名称：

  Highly Efficient Phosphate Diester Transesterification by a Calix[4]arene-Based Dinuclear Zinc(II) Catalyst

  摘要：

  DOI：

  10.1021/ja9638770