Methyl (3R,4S,5R)-5-Hydroxy-3,4-<(methoxymethylene)dioxy>cyclohex-1-ene-1-carboxylate | 91758-24-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Methyl (3R,4S,5R)-5-Hydroxy-3,4-<(methoxymethylene)dioxy>cyclohex-1-ene-1-carboxylate
• 英文别名: Methyl (3R,4S,5R)-5-Hydroxy-3,4-[(methoxymethylene)dioxy]cyclohex-1-ene-1-carboxylate；methyl (3aR,7R,7aS)-7-hydroxy-2-methoxy-3a,6,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate
• CAS: 91758-24-6；135711-52-3；135711-63-6
• 化学式: C₁₀H₁₄O₆
• 分子量: 230.218
• InChiKey: LBOLNOPIRNPDSM-UUBZBTQISA-N

物化性质

• 沸点：
  366.6±42.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.44
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Methyl (3R,4S,5R)-5-Hydroxy-3,4-<(methoxymethylene)dioxy>cyclohex-1-ene-1-carboxylate 在 咪唑 、 4-二甲氨基吡啶 、 重铬酸吡啶 、 碳酸氢钠 作用下， 以 盐酸 、 甲醇 、 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.83h， 生成
  参考文献：
  名称：

  Zamir, Lolita O.; Luthe, Corinne, Canadian Journal of Chemistry, 1984, vol. 62, p. 1169 - 1175

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,2R,6R)-6-hydroxy-4-(methoxycarbonyl)cyclohex-3-ene-1,2-diyl diacetate 在 sodium hydroxide 、 sodium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 Methyl (3R,4S,5R)-5-Hydroxy-3,4-<(methoxymethylene)dioxy>cyclohex-1-ene-1-carboxylate
  参考文献：
  名称：

  Zamir, Lolita O.; Luthe, Corinne, Canadian Journal of Chemistry, 1984, vol. 62, p. 1169 - 1175

  摘要：

  DOI：

文献信息

• Studies Directed Towards the Biosynthesis of the C7N Unit of Rifamycin B: A New Synthesis of Quinic Acid from Shikimic Acid
  作者：Rose-Marie Meier、Christoph Tamm

  DOI：10.1002/hlca.19910740415

  日期：1991.6.19

  The synthesis of quinic acid (4) via epoxide 13, starting from shikimic acid (5), is described (Scheme 1). Treatment of 13 with thiophenol yielded not only 17, but also the γ-lactones 18 and 19 as result of migration of silyl groups within a cis- and trans-diol system. The conversion provides a direct stereoselective epoxidation of a shikimic-acid derivative as well as an alternative pathway for the

  描述了从sh草酸（5）开始的经由环氧化物13的奎尼酸（4）的合成（方案1）。用甲硫酚处理13不仅产生17，而且由于顺式和反式二醇体系中甲硅烷基的迁移，还产生γ-内酯18和19。该转换提供了iki草酸衍生物的直接立体选择性环氧化以及制备4的替代途径。通过二甲苯化环氧化物的较短方法22由于获得了γ-内酯25代替了期望的α-羟基酯24（方案2），因此“β-内酯”是不成功的。
• Alberg, David G.; Lauhon, Charles T.; Nyfeler, Robert, Journal of the American Chemical Society, 1992, vol. 114, # 9, p. 3535 - 3546
  作者：Alberg, David G.、Lauhon, Charles T.、Nyfeler, Robert、Fässler, Alex、Bartlett, Paul A.

  DOI：——

  日期：——
• Targeting the Motion of Shikimate Kinase: Development of Competitive Inhibitors that Stabilize an Inactive Open Conformation of the Enzyme
  作者：Verónica Prado、Emilio Lence、María Maneiro、Juan C. Vázquez-Ucha、Alejandro Beceiro、Paul Thompson、Alastair R. Hawkins、Concepción González-Bello

  DOI：10.1021/acs.jmedchem.6b00483

  日期：2016.6.9

  The large conformational changes observed by Molecular Dynamics simulation studies on the product release in the LID and shikimic acid binding (SB) domains of the shikimate kinase (SK) enzyme have been exploited in the development of reversible competitive inhibitors against SK from Mycobacterium tuberculosis and Helicobacter pylori. This enzyme is a recognized target for antibiotic drug discovery. The reported C5-substituted shikimic acid analogues interact with the dynamic apolar pocket that surrounds the C4 and C5 hydroxyl groups of the natural substrate, cause the opening of the LID and SB domains, and capture the essential arginine far from the ATP binding site as required for catalysis. The 3-nitrobenzyl 3e and 5-benzothiophenyl derivatives 3i proved to be the most potent inhibitors. An ester prodrug of 3i was the most efficient derivative in achieving good in vitro activity against H. pylori, having a MIC value of 4 mu g/mL.