4'-aminomethyl-4,5'-dimethylisopsoralen | 80500-62-5

• 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: 4'-aminomethyl-4,5'-dimethylisopsoralen
• 英文别名: 4'-aminomethyl-4,5'-dimethylangelicin；9-(Aminomethyl)-4,8-dimethylfuro[2,3-h]chromen-2-one
• CAS: 80500-62-5
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: LNTKAMRXEIKMSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3,3-dimethylspiro[indoline-2,3'-naphtho[1,2-b][1,4]oxazine]-1-yl)propanoic acid 、 4'-aminomethyl-4,5'-dimethylisopsoralen 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以43%的产率得到N-[(4,8-dimethyl-2-oxofuro[2,3-h]chromen-9-yl)methyl]-3-(3',3'-dimethylspiro[benzo[f][1,4]benzoxazine-3,2'-indole]-1'-yl)propanamide
  参考文献：
  名称：

  Synthesis of New Spiropyrans and Spirooxazines Having a Heteroaromatic Pendant and Their Photochromic Behavior

  摘要：

  Two series of novel spiropyrans and spirooxazines having a heteroaromatic pendant were synthesized using two convenient methods. Their photochromic behaviors were investigated with the aid of absorption spectral measurements. The compounds showed several features different from the parent spiro compounds, including an inhibitory effect on the fatigue during the photochromic process of spiropyrans.

  DOI：

  10.3987/com-99-8663
• 作为产物：
  描述：

  7-(4-Chlorobut-2-ynoxy)-4-methylchromen-2-one 在 potassium phtalimide 、 一水合肼 、 N,N-二乙基苯胺 作用下， 反应 0.5h， 生成 4'-aminomethyl-4,5'-dimethylisopsoralen
  参考文献：
  名称：

  微波辅助的克莱森重排。在合成当归霉素衍生物中的应用

  摘要：

  通过4-甲基-7- [4-（羟基，氯，氨基，乙酰氧基和羟基）的克莱森重排，有效并快速地合成了4'-（羟基，氯，氨基，乙酰氧基和甲氧基）-甲基-4,5'-二甲基Angelicins。微波辐射下分别有甲氧基）-丁-2-炔氧基]-香豆素。这种新方法的优点包括操作简便，反应时间短，收率高以及易于使用的后处理程序。

  DOI：

  10.1002/jhet.5570430336

文献信息

• Synthesis of New Spiropyrans and Spirooxazines Having a Heteroaromatic Pendant and Their Photochromic Behavior
  作者：Xiaoliu Li、Yongmei Wang、Teruo Matsuura、Jiben Meng

  DOI：10.3987/com-99-8663

  日期：——

  Two series of novel spiropyrans and spirooxazines having a heteroaromatic pendant were synthesized using two convenient methods. Their photochromic behaviors were investigated with the aid of absorption spectral measurements. The compounds showed several features different from the parent spiro compounds, including an inhibitory effect on the fatigue during the photochromic process of spiropyrans.
• Microwave-assisted claisen rearrangement. Application to the synthesis of angelicin derivatives
  作者：Hassan Valizadeh、Abbas Shockravi

  DOI：10.1002/jhet.5570430336

  日期：2006.5

  acetoxy and methoxy)-methyl-4,5′-dimethylangelicins were efficiently and rapidly synthesized via Claisen rearrangement of 4-methyl-7-[4-(hydroxy, chloro, amino, acetoxy and methoxy)-but-2-ynyloxy]-coumarins respectively under microwave irradiation. Prominent among the advantages of this new method are operational simplicity, good yields in short reaction times and easy work-up procedures employed.

  通过4-甲基-7- [4-（羟基，氯，氨基，乙酰氧基和羟基）的克莱森重排，有效并快速地合成了4'-（羟基，氯，氨基，乙酰氧基和甲氧基）-甲基-4,5'-二甲基Angelicins。微波辐射下分别有甲氧基）-丁-2-炔氧基]-香豆素。这种新方法的优点包括操作简便，反应时间短，收率高以及易于使用的后处理程序。