α-2-<(1,3-dioxolan-2-yl)-4,5-dimethoxyphenyl>-3,4-dimethoxybenzyl alcohol | 116515-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-2-<(1,3-dioxolan-2-yl)-4,5-dimethoxyphenyl>-3,4-dimethoxybenzyl alcohol
• 英文别名: (3,4-Dimethoxyphenyl)-[2-(1,3-dioxolan-2-yl)-4,5-dimethoxyphenyl]methanol
• CAS: 116515-66-3
• 化学式: C₂₀H₂₄O₇
• 分子量: 376.406
• InChiKey: WBUPLLVHNXCWFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  α-2-<(1,3-dioxolan-2-yl)-4,5-dimethoxyphenyl>-3,4-dimethoxybenzyl alcohol 在 硫酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 2'-formyl-3,4,4',5'-tetramethoxybenzophenone
  参考文献：
  名称：

  Patil, P. A.; Joshi, R. R.; Narasimhan, N. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 1025 - 1029

  摘要：

  DOI：
• 作为产物：
  描述：

  6-溴藜芦醛 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 、 苯 为溶剂， 反应 0.33h， 生成 α-2-<(1,3-dioxolan-2-yl)-4,5-dimethoxyphenyl>-3,4-dimethoxybenzyl alcohol
  参考文献：
  名称：

  新型芳基萘木脂素作为抗癌剂的合成与生物评价

  摘要：

  合成了新型芳基萘木酚素，并通过1 H NMR，13 C NMR和HRMS建立了结构。通过MTT测定法评估这些化合物对癌细胞系的体外细胞毒性。化合物5d对KB细胞具有最高的细胞毒性。通过a啶橙和溴化乙锭双重染色法观察5d处理的KB细胞的凋亡。Western印迹分析显示5d通过线粒体途径诱导细胞凋亡，伴随Bax表达增加和Bcl-2表达减少。

  DOI：

  10.1007/s00044-012-0245-1

文献信息

• Charlton, James L.; Chee, Gaiklean; McColeman, Heather, Canadian Journal of Chemistry, 1995, vol. 73, # 9, p. 1454 - 1462
  作者：Charlton, James L.、Chee, Gaiklean、McColeman, Heather

  DOI：——

  日期：——
• Hindered Rotation in Arylnaphthalene Lignans
  作者：James L. Charlton、Curtis J. Oleschuk、Gaik-Lean Chee

  DOI：10.1021/jo952048e

  日期：1996.1.1

  Many arylnaphthalene lignans show biological activity and although few of them contain stereogenic centers, they may nevertheless be chiral if there is hindered rotation about the aryl-naphthalene bond. A relatively high barrier to rotation may give rise to separable rotational enantiomers (atropisomers) which might have quite different pharmacological properties. In order to investigate this possibility we have synthesized the natural products justicidin A, justicidin B, retro-helioxanthin, retro-justicidin B, and helioxanthin as well as four other arylnaphthalenes lignan analogs. We have studied the aryl-naphthalene rotational barrier in these compounds by dynamic NMR and HPLC and find barriers to rotation ranging from 16.9 to 21.5 kcal/mol. This translates to half-lives for individual atropisomers of less than 10 min at room temperature. The experimentally found barriers are compared to those obtained from molecular orbital calculations.
• PATIL, P. A.;JOSHI, R. R.;NARASIMHAN, N. S., INDIAN J. CHEM., 26,(1987) N 11, 1025-1029
  作者：PATIL, P. A.、JOSHI, R. R.、NARASIMHAN, N. S.

  DOI：——

  日期：——
• Synthesis and bioevaluation of novel arylnaphthalene lignans as anticancer agents
  作者：Yu Zhao、Jie Hui、Li Zhu

  DOI：10.1007/s00044-012-0245-1

  日期：2013.5

  Novel arylnaphthalene lignans were synthesized and their structures were established by 1H NMR, 13C NMR, and HRMS. These compounds were evaluated for their in vitro cytotoxicity against cancer cell lines by MTT assay. Compound 5d possessed the highest cytotoxicity against KB cells. Apoptosis of KB cells treated with 5d was observed by acridine orange and ethidium bromide double staining assay. Western

  合成了新型芳基萘木酚素，并通过1 H NMR，13 C NMR和HRMS建立了结构。通过MTT测定法评估这些化合物对癌细胞系的体外细胞毒性。化合物5d对KB细胞具有最高的细胞毒性。通过a啶橙和溴化乙锭双重染色法观察5d处理的KB细胞的凋亡。Western印迹分析显示5d通过线粒体途径诱导细胞凋亡，伴随Bax表达增加和Bcl-2表达减少。
• Patil, P. A.; Joshi, R. R.; Narasimhan, N. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 1025 - 1029
  作者：Patil, P. A.、Joshi, R. R.、Narasimhan, N. S.

  DOI：——

  日期：——