2-(3-bromo-4-methoxyphenyl)-2-methyl-1,3-dioxolane | 81224-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-bromo-4-methoxyphenyl)-2-methyl-1,3-dioxolane
• 英文别名: dioxolanne de la bromo-3 methoxy-4 acetophenone；3-bromo-4-methoxyacetophenone ethylene ketal
• CAS: 81224-34-2
• 化学式: C₁₁H₁₃BrO₃
• 分子量: 273.126
• InChiKey: UPGCPYYMXHKEBK-UHFFFAOYSA-N

物化性质

• 沸点：
  130 °C(Press: 0.05 Torr)
• 密度：
  1.410±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-bromo-4-methoxyphenyl)-2-methyl-1,3-dioxolane 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.45h， 生成 5-乙酰基-2-甲氧基苯甲醛
  参考文献：
  名称：

  Substituent control of intramolecular hydrogen bonding in formyl-protonated o-anisaldehydes: a stable ion and semiempirical MO investigation

  摘要：

  o-Anisaldehyde and its 5-Br, 5-F, 5-CF3, 5-CN, 5-NO2, and 5-COMe derivatives are protonated at the formyl group in 1:1 SbF5-FSO3H/SO2 (or SO2ClF) to give persistent carboxonium ions as mixtures of Z and E geometrical isomers. The cyano, nitro, and acetyl substituents are also protonated, leading to dications and additional geometrical isomers in the nitro and acetyl cases. The carboxonium ions are predominantly in the Z,syn configuration, but with increased amounts of the E,anti configuration with increased electron withdrawal by the substituents. With 5-NO2H+, E isomers become more abundant than Z. The formyl protonated 2-(trifluoromethoxy)benzaldehyde shows a strong preference for the E configuration. The preference for the Z,syn form is attributed to intramolecular hydrogen bonding that becomes less favorable as electron density is withdrawn from the methoxyl oxygen. The log Z/E values correlate with differences in energy content of the isomers predicted in AM1 calculations, and the chemical shift of the hydroxyl proton of the carboxonium group correlates well with predicted charge on the proton.

  DOI：

  10.1021/jo00058a018
• 作为产物：
  描述：

  2-溴苯甲醚 在 三氯化铝 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 2-(3-bromo-4-methoxyphenyl)-2-methyl-1,3-dioxolane
  参考文献：
  名称：

  Substituent control of intramolecular hydrogen bonding in formyl-protonated o-anisaldehydes: a stable ion and semiempirical MO investigation

  摘要：

  o-Anisaldehyde and its 5-Br, 5-F, 5-CF3, 5-CN, 5-NO2, and 5-COMe derivatives are protonated at the formyl group in 1:1 SbF5-FSO3H/SO2 (or SO2ClF) to give persistent carboxonium ions as mixtures of Z and E geometrical isomers. The cyano, nitro, and acetyl substituents are also protonated, leading to dications and additional geometrical isomers in the nitro and acetyl cases. The carboxonium ions are predominantly in the Z,syn configuration, but with increased amounts of the E,anti configuration with increased electron withdrawal by the substituents. With 5-NO2H+, E isomers become more abundant than Z. The formyl protonated 2-(trifluoromethoxy)benzaldehyde shows a strong preference for the E configuration. The preference for the Z,syn form is attributed to intramolecular hydrogen bonding that becomes less favorable as electron density is withdrawn from the methoxyl oxygen. The log Z/E values correlate with differences in energy content of the isomers predicted in AM1 calculations, and the chemical shift of the hydroxyl proton of the carboxonium group correlates well with predicted charge on the proton.

  DOI：

  10.1021/jo00058a018

文献信息

• A boronic acid chalcone analog of combretastatin A-4 as a potent anti-proliferation agent
  作者：Yali Kong、Kan Wang、Michael C. Edler、Ernest Hamel、Susan L. Mooberry、Mikell A. Paige、Milton L. Brown

  DOI：10.1016/j.bmc.2009.11.003

  日期：2010.1

  Chalcones represent a class of natural products that inhibits tubulin assembly. In this study we designed and synthesized boronic acid analogs of chalcones in an effort to compare biological activities with combretastatin A-4, a potent inhibitor of tubulin polymerization. Systematic evaluation of the positional effects of the carbonyl moiety towards inhibition of tubulin polymerization, cancer cell proliferation and angiogenesis revealed that placement of the carbonyl adjacent to the trimethoxybenzene A-ring resulted in more active compounds than when the carbonyl group was placed adjacent to the C-ring. Our study identified a boronic acid chalcone with inhibition towards 16 human cancer cell lines in the 10-200 nM range, and another three cell lines with GI(50)-values below 10 nM. Furthermore, this drug has significant anti-angiogenesis effects demonstrated by HUVEC tube formation and aortic ring assay. (C) 2009 Elsevier Ltd. All rights reserved.
• Kim, Phieo Ta; Guillard, Roger; Samreth, Soth, Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1373 - 1377
  作者：Kim, Phieo Ta、Guillard, Roger、Samreth, Soth、Sornay, Roland

  DOI：——

  日期：——
• KIM, PHIEO, TA;GUILARD, R.;SAMRETH, S.;SORNAY, R., J. HETEROCYCL. CHEM., 1981, 18, N 7, 1373-1377
  作者：KIM, PHIEO, TA、GUILARD, R.、SAMRETH, S.、SORNAY, R.

  DOI：——

  日期：——
• Substituent control of intramolecular hydrogen bonding in formyl-protonated o-anisaldehydes: a stable ion and semiempirical MO investigation
  作者：Kenneth K. Laali、Gerald F. Koser、Sundar Subramanyam、David A. Forsyth

  DOI：10.1021/jo00058a018

  日期：1993.3

  o-Anisaldehyde and its 5-Br, 5-F, 5-CF3, 5-CN, 5-NO2, and 5-COMe derivatives are protonated at the formyl group in 1:1 SbF5-FSO3H/SO2 (or SO2ClF) to give persistent carboxonium ions as mixtures of Z and E geometrical isomers. The cyano, nitro, and acetyl substituents are also protonated, leading to dications and additional geometrical isomers in the nitro and acetyl cases. The carboxonium ions are predominantly in the Z,syn configuration, but with increased amounts of the E,anti configuration with increased electron withdrawal by the substituents. With 5-NO2H+, E isomers become more abundant than Z. The formyl protonated 2-(trifluoromethoxy)benzaldehyde shows a strong preference for the E configuration. The preference for the Z,syn form is attributed to intramolecular hydrogen bonding that becomes less favorable as electron density is withdrawn from the methoxyl oxygen. The log Z/E values correlate with differences in energy content of the isomers predicted in AM1 calculations, and the chemical shift of the hydroxyl proton of the carboxonium group correlates well with predicted charge on the proton.