2-(t-butyldimethylsilanyloxy)-4,5-methylenedioxybenzaldehyde | 1192469-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(t-butyldimethylsilanyloxy)-4,5-methylenedioxybenzaldehyde
• 英文别名: 6-[(Tert-butyldimethylsilyl)oxy]-1,3-dioxaindane-5-carbaldehyde；6-[tert-butyl(dimethyl)silyl]oxy-1,3-benzodioxole-5-carbaldehyde
• CAS: 1192469-71-8
• 化学式: C₁₄H₂₀O₄Si
• 分子量: 280.396
• InChiKey: SKMPWOKFWYGSAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(t-butyldimethylsilanyloxy)-4,5-methylenedioxybenzaldehyde 、 N,N'-二甲基乙二胺 以 甲苯 为溶剂， 反应 6.0h， 以100%的产率得到2-[6-(t-butyldimethylsilanyloxy)benzo-1,3-dioxol-5-yl]-1,3-dimethylimidazolidine
  参考文献：
  名称：

  Toward establishing structure–activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells

  摘要：

  The presumption that some coumarins might be lead compounds in the search for new differentiation agents against leukemia is based on the fact that natural coumarins, 5-(3-methyl-2-butenyloxy)-6,7-methylenedioxycoumarin (C-2) and 5-methoxy-6,7-methylenedioxycoumarin (C-1) inhibit proliferation and induce differentiation in U-937 cells [Riveiro, M. E.; Shayo, C.; Monczor, F.; Fernandez, N.; Baldi, A.; De Kimpe, N.; Rossi, J.; Debenedetti, S.; Davio, C. Cancer Lett. 2004, 210, 179-188]. These promising findings prompted us to investigate the anti-leukemia activity of a broader range of related polyoxygenated coumarins. Twenty related natural or synthetically prepared coumarins, including a range of 5-substituted ayapin derivatives which have become easy accessible via newly developed synthesis methods, were evaluated, where treatments with 5-(2,3-dihydroxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-3) and 5-(2-hydroxy-3-methoxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-2) were able to inhibit the cell growth and induce the differentiation of U-937 cells after 48 h treatment. These results provide insight into the correlation between some structural properties of polyoxygenated coumarins and their in vitro leukemic differentiation activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.002
• 作为产物：
  描述：

  2-氨基-N-(2-氯-6-甲基苯基)-5-噻唑酰胺 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 2-(t-butyldimethylsilanyloxy)-4,5-methylenedioxybenzaldehyde
  参考文献：
  名称：

  Asymmetric (4+1) Annulations by Cascade Allylation and Transient σ‐Alkyl‐Pd(II) Initiated Allylic Csp3−H Activation

  摘要：

  A unique Pd‐catalyzed approach for asymmetric (4+1) annulations via cascade allylation and transient σ‐alkyl‐Pd(II) initiated methylene Csp3−H activation is reported. The enolate fragment derived from the decarboxylation of vinyl methylene carbonate is crucial to stabilize the key intermediate. These reactions enable the synthesis of various useful dihydrobenzofurans with excellent enantioselectivity, typically >95 : 5 er, and exclusive (Z)‐stereoselectivity. Compared with the well‐established annulations via Heck‐type C−H activations, this protocol showcases a conceptually new way to generate σ‐alkyl‐Pd(II) species that could initiate challenging asymmetric Csp3−H activations.

  DOI：

  10.1002/anie.202315438