9-aminothioxanthene 10,10-dioxide | 17313-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 英文名称: 9-aminothioxanthene 10,10-dioxide
• 英文别名: 9-Amino-thioxanthen-10,10-dioxid；10,10-dioxido-9H-thioxanthen-9-ylamine；10,10-dioxo-9H-thioxanthen-9-amine
• CAS: 17313-66-5
• 化学式: C₁₃H₁₁NO₂S
• 分子量: 245.302
• InChiKey: VOHDRWXJZAERDD-UHFFFAOYSA-N

物化性质

• 沸点：
  431.2±44.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-aminothioxanthene 10,10-dioxide 、 3-甲基-2-氧代丁酰乙酯 在 4 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 17.0h， 以75%的产率得到ethyl 2-[(10,10-dioxo-9H-thioxanthen-9-yl)imino]-3-methylbutanoate
  参考文献：
  名称：

  New Approach to Biomimetic Transamination Using Bifunctional [1,3]-Proton Transfer Catalysis in Thioxanthenyl Dioxide Imines

  摘要：

  A pyridoxamine equivalent, 9-aminothioxanthene 10,10-dioxide, has been designed that is capable of affording transamination in good to excellent yields of natural as well as artificial amino acids. Amidines and guanidines in catalytic amounts were capable of performing [1,3]-proton transfer in the imines under mild conditions, whereas various simple amines failed. The use of chiral catalysts resulted in modest asymmetric induction (ee less than or equal to 45%). The electronic dependence in para-substituted phenyl glyoxylate imines, isotope effects, and computational studies support a stepwise, bifunctional mechanism for amidine and guanidine catalysts. Attempts toward an autocatalytic model system are described.

  DOI：

  10.1021/jo0106748
• 作为产物：
  描述：

  10,10-二氧代噻吨-9-酮 在 吡啶 、 硼烷四氢呋喃络合物 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 生成 9-aminothioxanthene 10,10-dioxide
  参考文献：
  名称：

  New Approach to Biomimetic Transamination Using Bifunctional [1,3]-Proton Transfer Catalysis in Thioxanthenyl Dioxide Imines

  摘要：

  A pyridoxamine equivalent, 9-aminothioxanthene 10,10-dioxide, has been designed that is capable of affording transamination in good to excellent yields of natural as well as artificial amino acids. Amidines and guanidines in catalytic amounts were capable of performing [1,3]-proton transfer in the imines under mild conditions, whereas various simple amines failed. The use of chiral catalysts resulted in modest asymmetric induction (ee less than or equal to 45%). The electronic dependence in para-substituted phenyl glyoxylate imines, isotope effects, and computational studies support a stepwise, bifunctional mechanism for amidine and guanidine catalysts. Attempts toward an autocatalytic model system are described.

  DOI：

  10.1021/jo0106748

文献信息

• New Approach to Biomimetic Transamination Using Bifunctional [1,3]-Proton Transfer Catalysis in Thioxanthenyl Dioxide Imines
  作者：Anders Hjelmencrantz、Ulf Berg

  DOI：10.1021/jo0106748

  日期：2002.5.1

  A pyridoxamine equivalent, 9-aminothioxanthene 10,10-dioxide, has been designed that is capable of affording transamination in good to excellent yields of natural as well as artificial amino acids. Amidines and guanidines in catalytic amounts were capable of performing [1,3]-proton transfer in the imines under mild conditions, whereas various simple amines failed. The use of chiral catalysts resulted in modest asymmetric induction (ee less than or equal to 45%). The electronic dependence in para-substituted phenyl glyoxylate imines, isotope effects, and computational studies support a stepwise, bifunctional mechanism for amidine and guanidine catalysts. Attempts toward an autocatalytic model system are described.