dimethyl 4-(3-bromophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate | 93515-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: dimethyl 4-(3-bromophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(3'-bromophenyl)-1,4-dihydropyridine；Dimethyl 2,6-dimethyl-4-(3-bromophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 93515-16-3
• 化学式: C₁₇H₁₈BrNO₄
• 分子量: 380.238
• InChiKey: JPWHOMRZIVPQOM-UHFFFAOYSA-N

物化性质

• 沸点：
  460.9±45.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 4-(3-bromophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 以66%的产率得到6,8-dioxo-7-(3'-bromophenyl)-2,3,4,6,7,8-hexahydro(difuro)<3,4-b;3',-4'-e>pyridine
  参考文献：
  名称：

  Cardiovascular activity of difuropyridines

  摘要：

  DOI：

  10.1007/bf00772904
• 作为产物：
  描述：

  3-溴苯甲醇 、 乙酰乙酸甲酯 在 ammonium hydroxide 、 氢溴酸 、 二甲基亚砜 作用下， 以 水 为溶剂， 反应 2.53h， 以96%的产率得到dimethyl 4-(3-bromophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  HBr和DMSO通过无金属氧化C C偶联高效合成Hantzsch 1,4-二氢吡啶

  摘要：

  描述了一种通过无金属的氧化性C C偶联过程新型高效合成Hantzsch 1,4-二氢吡啶的方法。苄醇，1，3-二羰基化合物与氢氧化铵在HBr存在下于DMSO中于75°C进行反应，从而以极佳的收率得到1,4-二氢吡啶。该协议引入了使用苯甲醇代替醛作为Hantzsch反应的一种新方法。

  DOI：

  10.1016/j.tetlet.2018.10.010

文献信息

• Chiral Phosphoric Acid Catalyzed Enantioselective Desymmetrization of 1,4‐Dihydropyridines by C(sp ³ )−H Bromination
  作者：Min Han、Shi‐qi Zhang、Xin Cui、Qi‐wei Wang、Guang‐xun Li、Zhuo Tang

  DOI：10.1002/anie.202201418

  日期：2022.5.23

  used as substrates to obtain chiral Hantzsch-type 1,4-DHPs, which are frequently contained in pharmaceuticals. The inert C−H bond was converted into a versatile C−Br bond, which enabled the modification of the chiral 1,4-DHP derivatives with high efficiency by nucleophilic substitution. Furthermore, axially chiral 4-aryl pyridines were accessible by central-to-axial chirality conversion.

  容易获得的对称 1,4-二氢吡啶 (1,4-DHP) 被用作底物以获得药物中经常含有的手性 Hantzsch 型 1,4-DHP。惰性 C-H 键被转化为通用的 C-Br 键，从而能够通过亲核取代高效地修饰手性 1,4-DHP 衍生物。此外，轴向手性 4-芳基吡啶可通过中心到轴向手性转换获得。
• Process for preparation of certain tetrahydrofuro[3,4-b]pyridines
  申请人：Merck & Co., Inc.

  公开号：US04567268A1

  公开（公告）日：1986-01-28

  A facile process for the preparation of certain tetrahydrofuro[3,4-b]pyridines is described. The compounds have pharmacological properties useful in the study and treatment of cardiovascular diseases.

  本文描述了一种简便的方法制备某些四氢呋喃[3,4-b]吡啶化合物。这些化合物具有在心血管疾病的研究和治疗中有用的药理特性。
• Shinde, D. B.; Shinde, N. D.; Shingare, M. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 10, p. 920 - 922
  作者：Shinde, D. B.、Shinde, N. D.、Shingare, M. S.、Dubey, M. P.、Patnaik, G. K.

  DOI：——

  日期：——
• Mane, D. V.; Shinde, D. B.; Thore, S. N., Bulletin des Societes Chimiques Belges, 1997, vol. 106, # 3, p. 159 - 162
  作者：Mane, D. V.、Shinde, D. B.、Thore, S. N.、Bhawsar, S. B.、Shingare, M. S.

  DOI：——

  日期：——
• 1,4-Dihydropyridine antagonist activities at the calcium channel: a quantitative structure-activity relationship approach
  作者：Robert A. Coburn、Mark Wierzba、Mark J. Suto、Alan J. Solo、A. M. Triggle、David J. Triggle

  DOI：10.1021/jm00119a009

  日期：1988.11

  The effect of 46 1,4-dihydropyridine-type calcium channel antagonists on the tonic contractile response of longitudinal muscle strips of guinea pig ileum was determined. 2,6-Dimethyl-3,5-dicarbomethoxy-4-phenyl-1,4-dihydropyridine (13) and 13 ortho-, 15 meta-, and seven para-monosubstituted and 10 polysubstituted aromatic derivatives of 13 were studied. The pharmacological activities of the monosubstituted derivatives were best correlated by eq 10, log 1/C = 0.68 pi + 2.50 sigma m -0.47Lmeta -3.40B1para + 11.31, which had a correlation coefficient of 0.89. The full data set was best correlated by eq 11, log 1/C = 0.62 pi + 1.96 sigma m -0.44Lmeta -3.26B1para -1.51Lmeta' + 14.23, which had a correlation coefficient of 0.90. Equations of similar form but involving an ortho steric term were found to correlate the radioligand binding data for this class of compounds.