FENG Zhen,LI Jinlian,SHEN Xifeng,et al.Synthesis of betulin amine derivatives[J].Journal of Yanbian University,2021,47(01):47-55.
桦木醇胺衍生物的合成
- Title:
- Synthesis of betulin amine derivatives
- 文章编号:
- 1004-4353(2021)01-0047-09
- Keywords:
- betulin; derivative; secondary amine; diamine; acylation; amination
- 分类号:
- O629.9
- 文献标志码:
- A
- 摘要:
- 为了进一步开发和利用桦木醇衍生物,以桦木醇为起始物,在其C - 3、C - 28和C - 30上进行修饰,得到了28- O- [2-(吡咯烷- 1- 基)乙酰基]-桦木醇(2a)、 28- O- [2-(哌啶- 1- 基)乙酰基]-桦木醇(2b)、 28- O- [2-(吗啉-4- 基)乙酰基]-桦木醇(2c)、 28- O- [2-(哌嗪- 1- 基)乙酰基]-桦木醇(2d)、 28- O-(二甲氨基乙酰基)-桦木醇(2e)、 28- O-(二乙氨基乙酰基)-桦木醇(2f)、 28- O-(二丙氨基乙酰基)-桦木醇(2g)、 28- O-(二丁氨基乙酰基)-桦木醇(2h)、 28- O-(二戊氨基乙酰基)-桦木醇(2i)、 3,28- 二 - O- [2-(吡咯烷- 1- 基)乙酰基]-桦木醇(4a)、 3,28- 二 - O- [2-(哌啶- 1- 基)乙酰基]-桦木醇(4b)、 3,28- 二 - O- [2-(吗啉-4- 基)乙酰基]-桦木醇(4c)、 3,28- 二 - O- [2-(哌嗪- 1- 基)乙酰基]-桦木醇(4d)、 3,28- 二 - O-(二甲氨基乙酰基)-桦木醇(4e)、 3,28- 二 - O-(二乙氨基乙酰基)-桦木醇(4f)、 3,28- 二 - O-(二丙氨基乙酰基)-桦木醇(4g)、 3,28- 二 - O-(二丁氨基乙酰基)-桦木醇(4h)、 3,28- 二 - O-(二戊氨基乙酰基)-桦木醇(4i)、 3- O- [2-(吡咯烷- 1- 基)乙酰基]-桦木醇(6a)、 3- O- [2-(哌啶- 1- 基)乙酰基]-桦木醇(6b)、 3- O- [2-(吗啉-4- 基)乙酰基]-桦木醇(6c)、 3- O- [2-(哌嗪- 1- 基)乙酰基]-桦木醇(6d)、 3- O-(二甲氨基乙酰基)-桦木醇(6e)、 3- O-(二乙氨基乙酰基)-桦木醇(6f)、 3- O-(二丙氨基乙酰基)-桦木醇(6g)、 3- O-(二丁氨基乙酰基)-桦木醇(6h)、 3- O-(二戊氨基乙酰基)-桦木醇(6i)、 30-(1-吡咯烷基)桦木醇(9a)、 30-(1-哌啶基)桦木醇(9b)、 30-(4-吗啉基)桦木醇(9c)、 N,N' - 二 -(30-桦木醇基)哌嗪(9d)共31种桦木醇胺衍生物,并通过核磁共振氢谱(1H - NMR)、核磁共振碳谱(13C - NMR)、红外光谱(FT - IR)和基质辅助飞行时间质谱(MALDI - TOF - MS)对其结构进行了确认.
- Abstract:
- In ord In order to further develop and utilize betulin derivatives, betulin was uesd as the starting material, 31 betulin amine derivatives include 28 -O -[2 -(pyrrolidin-1-yl)acetyl]-betulin(2a), 28 -O -[2 -(piperidin-1-yl)acetyl]-betulin(2b), 28 -O -[2 -(morpholin-4-yl)acetyl]-betulin(2c), 28 -O -[2 -(piperazin-1-yl)acetyl]-betulin(2d), 28 -O -(Dimethylaminoacetyl)-betulin(2e), 28 -O -(Diethylaminoacetyl)-betulin(2f), 28 -O -(Dipropylaminoacetyl)-betulin(2g), 28 -O -(Dibutylaminoacetyl)-betulin(2h), 28 -O -(Dihexylaminoacetyl)-betulin(2i), 3,28 -Di -O -[2 -(pyrrolidin-1-yl)acetyl]-betulin(4a), 3,28 -Di -O -[2 -(piperidin-1-yl)acetyl]-betulin(4b), 3,28 -Di -O -[2 -(morpholin-4-yl)acetyl]-betulin(4c), 3,28 -Di -O -[2 -(piperazin-1-yl)acetyl]-betulin(4d), 3,28 -Di -O -(Dimethylaminoacetyl)-betulin(4e), 3,28 -Di -O -(Diethylaminoacetyl)-betulin(4f), 3,28 -Di -O -(Dipropylaminoacetyl)-betulin(4g), 3,28 -Di -O -(Dibutylaminoacetyl)-betulin(4h), 3,28 -Di -O -(Dihexylaminoacetyl)-betulin(4i), 3 -O -[2 -(pyrrolidin-1-yl)acetyl]-betulin(6a), 3 -O -[2 -(piperidin-1-yl)acetyl]-betulin(6b), 3 -O -[2 -(morpholin-4-yl)acetyl]-betulin(6c), 3 -O -[2 -(piperazin-1-yl)acetyl]-betulin(6d), 3 -O -(Dimethylaminoacetyl)-betulin(6e), 3 -O -(Diethylaminoacetyl)-betulin(6f), 3 -O -(Dipropylaminoacetyl)-betulin(6g), 3 -O -(Dibutylaminoacetyl)-betulin(6h), 3 -O -(Dihexylaminoacetyl)-betulin(6i), 30 -(1-pyrrolidine)-betulin(9a), 30 -(1 -piperidine)-betulin(9b), 30 -(4 -morpholine)-betulin(9c), N,N' -Di -(30 -betulinyl)piperazine(9d)were obtained by modifying C - 3, C - 28 and C - 30 of betulin, and their structure was confirmed by 1H - NMR, 13C - NMR, FT - IR and MALDI - TOF - MS.
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备注/Memo
收稿日期: 2020-12-03
基金项目: 国家自然科学基金(21362039)
*通信作者: 韩荣弼(1962—),男,教授,研究方向为有机合成化学.