4-n-Butyl-3-isopropoxy-3-cyclobutenedione 2-(ethylene acetal) | 128242-42-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 4-n-Butyl-3-isopropoxy-3-cyclobutenedione 2-(ethylene acetal)
• 英文别名: 4-n-butyl-3-isopropoxy-3-cyclobutene-1,2-dione 2-(ethylene acetal)；2-Butyl-1-propan-2-yloxy-5,8-dioxaspiro[3.4]oct-1-en-3-one
• CAS: 128242-42-2
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: YPKWJUOAADWBAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-n-Butyl-3-isopropoxy-3-cyclobutenedione 2-(ethylene acetal) 在 盐酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.41h， 生成 4-n-butyl-3-tert-butyl-3-cyclobutene-1,2-dione 2-(ethylene acetal)
  参考文献：
  名称：

  Regiospecific preparation of cyclobutenedione monoacetals

  摘要：

  DOI：

  10.1021/jo00306a011
• 作为产物：
  描述：

  2,3-bis(1-methylethoxy)-4-n-butyl-4-hydroxycyclobut-2-en-1-one 在 三氟甲磺酸三甲基硅酯 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 16.0h， 生成 4-n-Butyl-3-isopropoxy-3-cyclobutenedione 2-(ethylene acetal)
  参考文献：
  名称：

  Regiospecific preparation of cyclobutenedione monoacetals

  摘要：

  DOI：

  10.1021/jo00306a011

文献信息

• A general, regioselective synthesis of substituted benzocyclobutenedione monoacetals
  作者：James P. Edwards、Damian J. Krysan、Lanny S. Liebeskind

  DOI：10.1021/jo00067a029

  日期：1993.7

  A general, regioselective synthesis of substituted benzocyclobutenedione monoacetals is reported. Palladium-catalyzed coupling of a variety of 4-chlorocyclobutenones with 3-(tri-n-butylstannyl)-3-cyclobutene-1,2-dione 2-(ethylene acetal) and heating up to 70-100-degrees-C produces substituted benzocyclobutenedione monoacetals in good to excellent yields. Thia chemistry is presumed to proceed through palladium-catalyzed formation of a 3-(1-oxo-2-cyclobuten-4-yl)-3-cyclobutene-1,2-dione-2-(ethylene acetal) followed by a thermally induced ring opening to a dienyl ketene and subsequent six-electron electrocyclic ring closure and tautomerization. 2,3-Disubstituted 4-chlorocyclobutenones afford palladium intermediates which couple exclusively at the least-substituted allylic terminus. 2,3,4-Trisubstituted 4-chlorocyclobutenones have not been studied in detail; however, preliminary results suggest that regioselective allylic cross-coupling can be achieved. The methodology described provides an expedient and efficient route to previously difficult-to-prepare benzocyclobutenedione derivatives. These function as important synthetic intermediates in a variety of reactions developed in these and other laboratories.
• LIEBESKIND, LANNY S.;WIRTZ, KEVIN R., J. ORG. CHEM., 55,(1990) N9, C. 5350-5358
  作者：LIEBESKIND, LANNY S.、WIRTZ, KEVIN R.

  DOI：——

  日期：——