methyl 2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-carboxylate | 34818-55-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: methyl 2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-carboxylate
• 英文别名: methyl 2,2-dimethylchroman-6-carboxylate；2,2-dimethyl-chroman-6-carboxylic acid methyl ester；2,2-Dimethyl-chroman-6-carbonsaeure-methylester；Methyl 2,2-dimethyl-6-chromanecarboxylate；methyl 2,2-dimethyl-3,4-dihydrochromene-6-carboxylate
• CAS: 34818-55-8
• 化学式: C₁₃H₁₆O₃
• mdl: MFCD06203692
• 分子量: 220.268
• InChiKey: QOOSUIFPCJRCCM-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C(Solv: benzene (71-43-2))
• 沸点：
  322.6±21.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 生成 methyl 2,2-dimethyl-2H-1-benzopyran-6-carboxylate
  参考文献：
  名称：

  6-羧基-2,2-二甲基苯并二氢吡喃和色烯的合成

  摘要：

  在正磷酸的存在下，羟基苯甲酸及其甲酯与异戊二烯的缩合反应得到相应的2，2-二甲基苯并二氢吡喃，可以将其用DDQ或NBS脱氢得到相应的6-羧基-2，2-二甲基苯并二氢吡喃。也已经实现了天然化合物β-tubaicacid的合成。

  DOI：

  10.1016/0040-4020(82)80076-8
• 作为产物：
  描述：

  过氧化氢酶 在 盐酸 、 乙醚 、 sodium 作用下， 生成 methyl 2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-carboxylate
  参考文献：
  名称：

  Novobiocin. III. Cyclonovobiocic Acid, a Methyl Glycoside, and Other Reaction Products

  摘要：

  DOI：

  10.1021/ja01597a072

文献信息

• Bi(OTf)3-catalysed prenylation of electron-rich aryl ethers and phenols with isoprene: a direct route to prenylated derivatives
  作者：Katie E. Judd、Lorenzo Caggiano

  DOI：10.1039/c1ob05365e

  日期：——

  Electron-rich aryl ethers and phenols react with isoprene (2-methylbuta-1,3-diene) in the presence of catalytic Bi(OTf)3 at 40 °C to afford the corresponding prenylated or 2,2-dimethylchroman products, respectively, in moderate to good yields. This transformation offers a convenient and expedient entry to prenylated derivatives of electron-rich aromatics that often display enhanced biological activities

  富含电子的芳基醚和酚与 异戊二烯 （2-甲基丁-1,3-二烯）在40°C下存在催化Bi（OTf）3的情况下提供相应的烯丙基化或2,2-二甲基苯并吡喃产品分别以中等到良好的产量。这种转变为通常显示出增强的生物活性的富含电子的芳族化合物的烯丙基化衍生物的进入提供了方便和便利的途径。该方法已用于生物活性天然产物和相关化合物的有效合成中。
• [EN] INHIBITORS OF LYSINE METHYL TRANSFERASE<br/>[FR] INHIBITEURS DE LA LYSINE MÉTHYLTRANSFÉRASE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015077194A1

  公开（公告）日：2015-05-28

  There are disclosed compounds that are inhibitors of EZH2, pharmaceutical compositions containing said compounds and methods of treating hyperproliferative, inflammatory, infectious, and immunoregulatory disorders and diseases utilizing the compounds of the invention.

  已披露的化合物是EZH2的抑制剂，包含这些化合物的药物组合物以及利用本发明的化合物治疗过度增殖、炎症、感染和免疫调节性疾病的方法。
• Natural Chromenes and Chromene Derivatives as Potential Anti-trypanosomal Agents
  作者：João Marcos Batista Jr.、Adriana Aparecida Lopes、Daniela Luz Ambrósio、Luis Octávio Regasini、Massuo Jorge Kato、Vanderlan da Silva Bolzani、Regina Maria Barretto Cicarelli、Maysa Furlan

  DOI：10.1248/bpb.31.538

  日期：——

  The aim of the study was to investigate the anti-trypanocidal activities of natural chromene and chromene derivatives. Five chromenes were isolated from Piper gaudichaudianum and P. aduncum, and a further seven derivatives were prepared using standard reduction, methylation and acetylation procedures. These compounds were assayed in vitro against epimastigote forms of Trypanosoma cruzi, the causative agent of Chagas disease. The results showed that the most of the compounds, especially those possessing electron-donating groups as substituents on the aromatic ring, showed potent trypanocidal activity. The most active compound, [(2S)-methyl-2-methyl-8-(3″-methylbut-2″-enyl)-2-(4′-methylpent-3′-enyl)-2H-chromene-6-carboxylate], was almost four times more potent than benznidazole (the positive control) and showed an IC50 of 2.82 μM. The results reveal that chromenes exhibit significant anti-trypanocidal activities and indicate that this class of natural product should be considered further in the development of new and more potent drugs for use in the treatment of Chagas disease.

  该研究的目的是研究天然色烯和色烯衍生物的抗锥虫活性。从 Piper gaudichaudianum 和 P. aduncum 中分离出五种色烯，并使用标准还原、甲基化和乙酰化程序制备了另外七种衍生物。这些化合物在体外针对克氏锥虫（恰加斯病的病原体）的上鞭毛体形式进行了测定。结果表明，大多数化合物，尤其是芳香环上具有给电子基团取代基的化合物，显示出有效的杀锥虫活性。最活跃的化合物，[(2S)-甲基-2-甲基-8-(3″-甲基丁-2″-烯基)-2-(4′-甲基戊-3′-烯基)-2H-色烯-6-羧酸盐]，其效力几乎是苯并硝唑（阳性对照）的四倍，IC50 为 2.82 μM。结果表明，色烯表现出显着的抗锥虫活性，并表明在开发用于治疗南美锥虫病的新的、更有效的药物时应进一步考虑此类天然产物。
• Fatope, Majekodunmi O.; Adeniyl, Adebayo E., Synthetic Communications, 1985, vol. 15, # 4, p. 307 - 310
  作者：Fatope, Majekodunmi O.、Adeniyl, Adebayo E.

  DOI：——

  日期：——
• A chromene an isoprenylated methyl hydroxybenzoate and a C-methyl flavanone from the bark of Piper hostmannianum
  作者：Pedro P.、D. Díaz、Tiberio Arias C.、Pedro Joseph-Nathan

  DOI：10.1016/s0031-9422(00)84792-5

  日期：1987.1