InChIKey | ZGLXUQQMLLIKAN-SVIJTADQSA-N |
Inchi | 1S/C22H22O7/c1-24-17-6-12(7-18(25-2)21(17)26-3)19-14-8-16-15(28-10-29-16)5-11(14)4-13-9-27-22(23)20(13)19/h5-8,13,19-20H,4,9-10H2,1-3H3/t13-,19+,20-/m0/s1 |
SMILES | O1C([C@]2([H])[C@]([H])(C3C([H])=C(C(=C(C=3[H])OC([H])([H])[H])OC([H])([H])[H])OC([H])([H])[H])C3=C([H])C4=C(C([H])=C3C([H])([H])[C@@]2([H])C1([H])[H])OC([H])([H])O4)=O |
LogP | 2.91830 |
PSA | 72.45000 |
折射率 | 1.587 |
沸点 | 564.5ºC at 760 mmHg |
闪点 | 247ºC |
颜色与性状 | Powder |
密度 | 1.304g/cm3 |
精确分子量 | 398.13700 |
氢键供体数量 | 0 |
氢键受体数量 | 7 |
可旋转化学键数量 | 4 |
同位素质量 | 398.137 |
重原子数量 | 29 |
复杂度 | 598 |
同位素原子数量 | 0 |
确定原子立构中心数量 | 3 |
不确定原子立构中心数量 | 0 |
确定化学键立构中心数量 | 0 |
不确定化学键立构中心数量 | 0 |
共价键单元数量 | 1 |
疏水参数计算参考值(XlogP) | 3.1 |
拓扑分子极性表面积 | 72.4 |
分子量 | 398.4 |
用途 | 1、去氧鬼臼毒素具有抗肿瘤活性。 |
1.
Biosynthesis of yatein in Anthriscus sylvestris
Norikazu Sakakibara,Shiro Suzuki,Toshiaki Umezawa,Mikio Shimada Org. Biomol. Chem. 2003 1 2474
2.
Stereocontrolled synthesis of (±)-deoxypodophyllotoxin via the benzyl equivalent of the Peterson reaction
Seiichi Takano,Shizuo Otaki,Kunio Ogasawara J. Chem. Soc. Chem. Commun. 1985 485
3.
Regioselective suprafacial 1,5-hydrogen shifts in o-quinodimethanes; a route to 4-deoxypodophyllotoxin
David W. Jones,Adrian M. Thompson J. Chem. Soc. Chem. Commun. 1988 1095
4.
Biosynthesis, total synthesis, and pharmacological activities of aryltetralin-type lignan podophyllotoxin and its derivatives
Siyu Shen,Yuru Tong,Yunfeng Luo,Luqi Huang,Wei Gao Nat. Prod. Rep. 2022 39 1856
5.
Design, synthesis and biological evaluation of 4′-demethyl-4-deoxypodophyllotoxin derivatives as novel tubulin and histone deacetylase dual inhibitors
Xuan Zhang,Jie Zhang,Mingbo Su,Yubo Zhou,Yi Chen,Jia Li,Wei Lu RSC Adv. 2014 4 40444
6.
Recent advances in the total synthesis of 2,7′-cyclolignans
Han-Qiu Zhang,Chu-Xuan Yan,Jian Xiao,Ya-Wen Wang,Yu Peng Org. Biomol. Chem. 2022 20 1623
7.
Synthesis of (±)-4-deoxypodophyllotoxin, (±)-podophyllotoxin and (±)-epipodophyllotoxin
David W. Jones,Adrian M. Thompson J. Chem. Soc. Perkin Trans. 1 1993 2541
8.
Synthesis of 2,4-diaza-4-deoxypodophyllotoxin, a new analogue of podophyllotoxin possessing antitumour activity
Yukio Hitotsuyanagi,Yoichi Naka,Keiji Yamagami,Akihiro Fujii,Tetsuya Tahara J. Chem. Soc. Chem. Commun. 1995 49
9.
Notes
A. I. Biggs,J. Baddiley,N. A. Hughes,A. L. James,K. B. L. Mathur,H. S. Mehra,Frank S. H. Head,M. M. Williamson,A. F. Trotman-Dickenson,G. J. O. Verbeke,C. C. Barraclough,J. Lewis,R. S. Nyholm,I. R. Beattie,T. Gilson,M. D. Patel,J. M. Rowson,D. A. H. Taylor,J. R. B. Boocock,W. J. Hickinbottom,J. Davoll,K. A. Kerridge,A. R. Battersby,I. A. Greenock,J. R. Miller,A. G. Sharpe,J. Biggs,P. Sykes,H. J. Emeléus,D. E. MacDuffie,B. F. Cain J. Chem. Soc. 1961 2572
10.
New frontiers in the transition-metal-free synthesis of heterocycles from alkynoates: an overview and current status
Imtiaz Khan,Sumera Zaib,Aliya Ibrar Org. Chem. Front. 2020 7 3734
SMILES
COC1C=C(C=C(OC)C=1OC)[C@@H]2C3C(=CC4=C(OCO4)C=3)C[C@@H]5[C@@H]2C(=O)OC5