3-(1-butyl)-4-methoxy-3-cyclobutene-1,2-dione | 102683-52-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(1-butyl)-4-methoxy-3-cyclobutene-1,2-dione
• 英文别名: 3-n-Butyl-4-methoxy-3-cyclobutene-1,2-dione；3-n-butyl-4-methoxycyclobut-3-ene-1,2-dione；4-n-butyl-3-methoxy-3-cyclobutene-1,2-dione；3-butyl-4-methoxy-3-cyclobutene-1,2-dione；3-n-butyl-4-methoxycyclobutenedione；2-butyl-3-methoxycyclobutenedione；3-Butyl-4-methoxycyclobut-3-ene-1,2-dione
• CAS: 102683-52-3
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: HQYVBGIRQSCYGF-UHFFFAOYSA-N

物化性质

• 沸点：
  268.8±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1-butyl)-4-methoxy-3-cyclobutene-1,2-dione 在 叔丁基锂 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 2-n-butyl-3-methoxy-5-(phenylmethyl)-2,5-cyclohexadiene-1,4-dione
  参考文献：
  名称：

  Perri, Steven T.; Moore, Harold W., Journal of the American Chemical Society, 1990, vol. 112, # 5, p. 1897 - 1905

  摘要：

  DOI：
• 作为产物：
  描述：

  正丁基锂 、 3,4-二甲氧基-3-环丁烯-1,2-二酮 以 四氢呋喃 为溶剂， 反应 0.17h， 以44%的产率得到3-(1-butyl)-4-methoxy-3-cyclobutene-1,2-dione
  参考文献：
  名称：

  General regiospecific synthesis of annulated quinones

  摘要：

  DOI：

  10.1021/jo00240a011

文献信息

• Formation of reactive o-quinone methides from the reaction of trimethylsilyl(methyl)-substituted 1,4-benzoquinones with nucleophiles
  作者：John E. Ezcurra、Kostas Karabelas、Harold W. Moore

  DOI：10.1016/j.tet.2004.09.052

  日期：2005.1

  o-Quinone methides are formed from the reaction of nucleophiles with trimethylsilyl(methyl)-1,4-benzoquinones. These reactive intermediates are trapped by excess nucleophile to form substituted quinones following oxidation. In addition, varying amounts of a symmetrical dimer and a xanthen derivative were observed. The influence of different nucleophiles and ring substituents on the rate of reaction

  邻醌甲基化物是由亲核试剂与三甲基甲硅烷基（甲基）-1,4-苯醌反应形成的。这些反应性中间体被过量的亲核试剂捕获，在氧化后形成取代的醌。另外，观察到变化量的对称二聚体和a吨衍生物。已经研究了不同亲核试剂和环取代基对反应速率的影响，并且与由亲核试剂攻击甲硅烷基基团引发的乙烯基烯醇化物的限速形成相一致。
• Synthesis of indolizine-5,8-diones and [3.2.2]cyclazines
  作者：Benjamin R. Yerxa、Harold W. Moore

  DOI：10.1016/s0040-4039(00)74750-2

  日期：1992.12

  subsequent oxidation to the rare indolizine-5,8-diones is described. When the rearrangement is carried out in the presence of DMAD the indolizines are trapped in an 8+2 cycloaddition to give [3.2.2]cyclazines.

  描述了热诱导的4-（1-吡咯基）-4-三甲基甲硅烷氧基环丁烯酮的环膨胀成5-羟基-8-三甲基甲硅烷氧基吲哚并随后氧化成稀有的吲哚嗪-5，8-二酮。当在DMAD存在下进行重排时，吲哚嗪被困在8 + 2环加成反应中，生成[3.2.2]环嗪。
• Squaric acid derivatives
  申请人：——

  公开号：US20030162799A1

  公开（公告）日：2003-08-28

  Squaric acid Derivatives of formula (1) are described: 1 wherein R 1 is an integrin binding group; R 2 is a hydrogen atom or a C 1-6 alkyl group; L 1 is a covalent bond or a linker atom or group; n is zero or the integer 1; Alk 1 is an optionally substituted aliphatic chain; R 3 is a hydrogen atom or an optionally substituted heteroaliphatic, cycloaliphatic, heterocycloaliphatic, polycycloaliphatic, polyheterocycloaliphatic, aromatic or heteroaromatic group: and the salts, solvates, hydrates and N-oxides thereof. The compounds are able to inhibit the binding of integrins to their ligands and are of use in the prophylaxis and treatment of immune of inflammatory disorders, or disorders involving the inappropriate growth or migration of cells.

  本文介绍了公式（1）的苯丙酸衍生物：其中R1是整合素结合基；R2是氢原子或C1-6烷基基团；L1是共价键或连接原子或基团；n为零或整数1；Alk1是可选的取代脂肪链；R3是氢原子或可选的取代杂原子脂肪、环状脂肪、杂环状脂肪、多环状脂肪、多杂环状脂肪、芳香或杂芳基团；以及其盐、溶剂化合物、水合物和N-氧化物。这些化合物能够抑制整合素与其配体的结合，并可用于预防和治疗免疫或炎症性疾病，或涉及细胞不适当生长或迁移的疾病。
• REARRANGEMENT OF 4-ARYL-4-HYDROXY-2,3-DIALKOXYCYCLOBUTENONES TO ANNULATED HYDROQUINONES AND QUINONES: 5,6-DIETHOXYBENZOFURAN-4,7-DIONE
  作者：Perri、Rice、Moore

  DOI：10.15227/orgsyn.069.0220

  日期：——
• <i>o</i>-Quinone Methides from 4-Allenylcyclobutenones:  Synthesis and Chemistry
  作者：Meng Taing、Harold W. Moore

  DOI：10.1021/jo951445m

  日期：1996.1.1

  Selected 4-allenylcyclobutenones ring expand to the corresponding o-quinone methides upon thermolysis in refluxing toluene or benzene. These reactive intermediates were not isolated but trapped to give stable products. The reaction has synthetic potential as a route to highly-substituted phenols, benzofurans, and aryl analogs of hexahydrocannabinol. In addition, a unique rearrangement involving a methyl migration from silicon to carbon of selected 4-[3,3-bis(trimethylsilyl)-1,2-propadienyl]cyclobutenones to give 1,2-benzoxasilols is described. Finally, data are presented that show rapid rotation around the alkylidene bond of o-quinone methides at 30 degrees C and that 2-(1-methylethenyl)phenols are in equilibrium with the corresponding o-quinone methides.