2-甲基-2-(3-硝基苯基)-1,3-二噁戊环 | 51226-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲基-2-(3-硝基苯基)-1,3-二噁戊环
• 英文名称: 2-methyl-2-(3-nitrophenyl)-[1,3]dioxolane
• 英文别名: 2-methyl-2-(3-nitrophenyl)-1,3-dioxolane；2-methyl-2-(3-nitro-phenyl)-[1,3]dioxolane
• CAS: 51226-13-2
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: GMSSLCFXSWWJOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-2-(3-硝基苯基)-1,3-二噁戊环 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、5.0 MPa 条件下， 反应 0.5h， 以93%的产率得到3-(2-甲基-1,3-二氧烷-2-基)苯胺
  参考文献：
  名称：

  Phenazines and Natural Products; Novel Synthesis of Saphenic Acid

  摘要：

  DOI：

  10.1055/s-1999-3587
• 作为产物：
  描述：

  乙二醇 、 间硝基苯乙酮 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 2-甲基-2-(3-硝基苯基)-1,3-二噁戊环
  参考文献：
  名称：

  SmI 2 /胺/水对甲苯磺酰胺和酯的瞬时脱保护

  摘要：

  SmI 2 /胺/水介导甲苯磺酰胺和甲苯磺酯的瞬时裂解。高度受阻，敏感和功能化的底物以接近定量的收率成功脱保护。

  DOI：

  10.1021/ol802243d

文献信息

• Aromatic Nitration under Neutral Conditions Using Nitrogen Dioxide and Ozone as the Nitrating Agent. Application to Aromatic Acetals and Acylal
  作者：Hitomi Suzuki、Shuji Yonezawa、Tadashi Mori

  DOI：10.1246/bcsj.68.1535

  日期：1995.6

  can be nitrated smoothly with nitrogen dioxide in ice-cooled dichloromethane or acetonitrile in the presence of ozone and magnesium oxide to give ortho- and para-nitro derivatives as the major product in good combined yields, the acetal ring as a protective group remaining almost intact. An acylal derived from benzaldehyde similarly undergoes nitration on the aromatic ring to give an isomeric mixture

  在臭氧和氧化镁存在下，芳香羰基化合物衍生的环状缩醛可以在冰冷的二氯甲烷或乙腈中用二氧化氮顺利硝化，得到邻和对硝基衍生物作为主要产物，收率良好，缩醛环作为保护基团几乎完好无损。衍生自苯甲醛的酰基类似地在芳环上硝化，得到三种硝基化合物的异构混合物，其中邻位异构体和间位异构体占主导地位，而芳族原酸酯迅速分解为简单的母体酯。中性条件下的环硝化反应被解释为一种非经典机制，其中三氧化氮作为初始亲电子试剂参与。
• Instantaneous Deprotection of Tosylamides and Esters with SmI₂/Amine/Water
  作者：Tobias Ankner、Göran Hilmersson

  DOI：10.1021/ol802243d

  日期：2009.2.5

  SmI2/amine/water mediates instantaneous cleavage of tosyl amides and tosyl esters. Highly hindered, sensitive and functionalized substrates were successfully deprotected in near quantitative yield.

  SmI 2 /胺/水介导甲苯磺酰胺和甲苯磺酯的瞬时裂解。高度受阻，敏感和功能化的底物以接近定量的收率成功脱保护。
• 18O-isotope effect in13C nuclear magnetic resonance spectroscopy: 5—Substituent group electronic effects in substituted acetophenones
  作者：John M. Risley、Shawn A. DeFrees、Robert L. Van Etten

  DOI：10.1002/omr.1270210108

  日期：1983.1

  AbstractA series of para‐ and meta‐substituted acetophenones were prepared which were highly labeled with 18O at the carbonyl function. The natural abundance 13C NMR spectra of the compounds were recorded and the 18O‐isotope‐induced shifts of the carbonyl carbon were measured in order to determine possible substituent group electronic effects on the 18O‐isotope shift. The isotope shifts were found to be correlated with a number of properties which demonstrate the molecular basis of the isotope shift. Good correlations were obtained for the isotope shift as a function of σp+, the carbonyl stretching frequency, the carbonyl group bond order, the n→π**transition of the carbonyl group and the chemical shift of the ipso carbon. In contrast, no correlation was observed between the magnitude of the 18O‐induced isotope shift and the 13C chemical shift of the carbonyl carbon. These properties are discussed in connection with the theoretical basis of the isotope shift.
• Design, Synthesis, and Evaluation of Indolinones as Triple Angiokinase Inhibitors and the Discovery of a Highly Specific 6-Methoxycarbonyl-Substituted Indolinone (BIBF 1120)
  作者：Gerald J. Roth、Armin Heckel、Florian Colbatzky、Sandra Handschuh、Jörg Kley、Thorsten Lehmann-Lintz、Ralf Lotz、Ulrike Tontsch-Grunt、Rainer Walter、Frank Hilberg

  DOI：10.1021/jm900431g

  日期：2009.7.23

  Inhibition of tumor angiogenesis through blockade of the vascular endothelial growth factor (VEGF) signaling pathway is a new treatment modality in oncology. Preclinical findings suggest that blockade of additional pro-angiogenic kinases, such as Fibroblast and platelet-derived growth factor receptors (FGFR and PDGFR), may improve the efficacy of pharmacological cancer treatment. Indolinones substituted in position 6 were identified as selective inhibitors of VEGF-, PDGF-, and FGF-receptor kinases. In particular, 6-methoxycarbonyl-substituted indolinones showed a highly favorable selectivity profile. Optimization identified potent inhibitors of VEGF-related endothelial cell proliferation with additional efficacy on pericyctes and smooth muscle cells. In contrast, no direct inhibition of tumor cell proliferation was observed. Compounds 2 (BIBF 1000) and 3 (BIBF 1120) are orally available and display encouraging efficacy in in vivo tumor models while being well tolerated. The triple angiokinase inhibitor 3 is currently in phase III clinical trials for the treatment of nonsmall cell lung cancer.
• Suzuki, Hitomi; Yonezawa, Shuji; Mori, Tadashi, Journal of the Chemical Society. Perkin transactions I, 1994, # 11, p. 1367 - 1370
  作者：Suzuki, Hitomi、Yonezawa, Shuji、Mori, Tadashi、Maeda, Koichi

  DOI：——

  日期：——