(S)-N,N-bis(2-quinolylmethyl)methionine | 247105-54-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N,N-bis(2-quinolylmethyl)methionine
• 英文别名: (2S)-2-[bis(quinolin-2-ylmethyl)amino]-4-methylsulfanylbutanoic acid
• CAS: 247105-54-0
• 化学式: C₂₅H₂₅N₃O₂S
• 分子量: 431.558
• InChiKey: HXOWUWLQPNNEAQ-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  91.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-N,N-bis(2-quinolylmethyl)methionine 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 以 二氯甲烷 为溶剂， 以82%的产率得到Cu((S)-N,N-bis(2-quinolylmethyl)methionine)PF6
  参考文献：
  名称：

  Redox-Induced Ligand Reorganization and Helicity Inversion in Copper Complexes of N,N-Dialkylmethionine Derivatives

  摘要：

  N, N'-Dipicolyl, bis(stilbylvinylpyridylmethyl), and diquinaldyl methionine derivatives form stable Cu-II complexes with metal ligation by three nitrogen atoms and the carboxylate. One-electron reduction results in the exchange of carboxylate for sulfide in the complexes. This ligand reorganization is accompanied by inversion of the helical orientation of the two arms containing nitrogen heterocycles, resulting in nearly mirror image circular dichroism spectra. This paper provides details for the synthesis of these complexes and the evidence for the remarkable stereochemical interconversion that accompanies the reduction reaction. Detailed analysis of the electronic spectra of the ligands and metal complexes is provided along with X-ray crystallographic structures of Cu-II and Zn-II complexes of the N, N'-dipicolylmethionine complexes.

  DOI：

  10.1021/ic060660q
• 作为产物：
  描述：

  2-溴甲基喹啉 、 L-蛋氨酸 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (S)-N,N-bis(2-quinolylmethyl)methionine
  参考文献：
  名称：

  N，N-二烷基α-氨基酸和β-氨基醇的绝对构型，来自Cu（II）配合物的激子耦合圆二色性光谱。

  摘要：

  圆二色性技术已通过一步衍生化过程（需要微克数量的材料）应用于具有单个立体生成中心的无环α-氨基酸和β-氨基醇的绝对构型分配。金属离子固定了两个生色团的几何关系，根据金属配合物中配体的预期构象，提供了与理论相符的CD光谱。

  DOI：

  10.1021/ol990715a

文献信息

• Redox-Induced Ligand Reorganization and Helicity Inversion in Copper Complexes of <i>N</i>,<i>N</i>-Dialkylmethionine Derivatives
  作者：Steffen Zahn、Debasis Das、James W. Canary

  DOI：10.1021/ic060660q

  日期：2006.7.1

  N, N'-Dipicolyl, bis(stilbylvinylpyridylmethyl), and diquinaldyl methionine derivatives form stable Cu-II complexes with metal ligation by three nitrogen atoms and the carboxylate. One-electron reduction results in the exchange of carboxylate for sulfide in the complexes. This ligand reorganization is accompanied by inversion of the helical orientation of the two arms containing nitrogen heterocycles, resulting in nearly mirror image circular dichroism spectra. This paper provides details for the synthesis of these complexes and the evidence for the remarkable stereochemical interconversion that accompanies the reduction reaction. Detailed analysis of the electronic spectra of the ligands and metal complexes is provided along with X-ray crystallographic structures of Cu-II and Zn-II complexes of the N, N'-dipicolylmethionine complexes.
• Absolute Configurations of <i>N</i>,<i>N</i>-Dialkyl α-Amino Acids and β-Amino Alcohols from Exciton-Coupled Circular Dichroism Spectra of Cu(II) Complexes
  作者：Steffen Zahn、James W. Canary

  DOI：10.1021/ol990715a

  日期：1999.9.1

  [formula: see text] A circular dichroism technique has been applied to the absolute configurational assignment of acyclic alpha-amino acids and beta-amino alcohols with single stereogenic centers via a one-step derivitization procedure requiring microgram quantities of material. Metal ions fix the geometrical relationship of two chromophores, affording CD spectra that agree with theory on the basis

  圆二色性技术已通过一步衍生化过程（需要微克数量的材料）应用于具有单个立体生成中心的无环α-氨基酸和β-氨基醇的绝对构型分配。金属离子固定了两个生色团的几何关系，根据金属配合物中配体的预期构象，提供了与理论相符的CD光谱。