3-tert-Butoxy-3-cyclobutene-1,2-dione | 134056-32-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-tert-Butoxy-3-cyclobutene-1,2-dione
• 英文别名: 3-Cyclobutene-1,2-dione, 3-(1,1-dimethylethoxy)-；3-[(2-methylpropan-2-yl)oxy]cyclobut-3-ene-1,2-dione
• CAS: 134056-32-9
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: ZURAENGLNSXLBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-tert-Butoxy-3-cyclobutene-1,2-dione 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.33h， 生成 3-tert-Butoxy-4-methoxy-4-methyl-2-cyclobuten-1-ol
  参考文献：
  名称：

  A method for the stereoselective construction of 4-alkoxy-5-alkylidenecyclopentenones by the tandem ring expansion-functionalization of 1-alkynylcyclobutenols using a palladium-mercury cocatalytic system

  摘要：

  1-(1-Alkynyl)-4-methoxy-4-methyl-2-cyclobutenols, prepared by nucleophilic functionalization of cyclobutenediones, were transformed with high stereoselectivity into 4-methoxy-4-methyl-5-alkylidenecyclopentenones. The action of stoichiometric Hg(OCOCF3)(2) and then metathesis with NaCl produced 5-(1-(chloromercurio)alkylidene)-4-methoxy-4-methyl-2-cyclopentenones which were stereospecifically functionalized by palladium-mediated allylation and hydroxybutenylation. Treatment with Br-2/DMSO led to stereospecific bromodemercuration. The 1-(1-alkynyl)-4-methoxy-4-methyl-2-cyclobutenols underwent efficient and very stereoselective tandem ring expansion-functionalizations in the presence of three different allylic chlorides and a catalyst system composed of 10% Hg(OCOCF3)(2) and 10% PdCl2. All products can be obtained with a stereoselectivity greater than 99:1 at the exocyclic alkene.

  DOI：

  10.1021/jo00084a038
• 作为产物：
  描述：

  2,3-二叔丁氧基-4-羟基-2-环丁烯-1-酮 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以91%的产率得到3-tert-Butoxy-3-cyclobutene-1,2-dione
  参考文献：
  名称：

  A method for the stereoselective construction of 4-alkoxy-5-alkylidenecyclopentenones by the tandem ring expansion-functionalization of 1-alkynylcyclobutenols using a palladium-mercury cocatalytic system

  摘要：

  1-(1-Alkynyl)-4-methoxy-4-methyl-2-cyclobutenols, prepared by nucleophilic functionalization of cyclobutenediones, were transformed with high stereoselectivity into 4-methoxy-4-methyl-5-alkylidenecyclopentenones. The action of stoichiometric Hg(OCOCF3)(2) and then metathesis with NaCl produced 5-(1-(chloromercurio)alkylidene)-4-methoxy-4-methyl-2-cyclopentenones which were stereospecifically functionalized by palladium-mediated allylation and hydroxybutenylation. Treatment with Br-2/DMSO led to stereospecific bromodemercuration. The 1-(1-alkynyl)-4-methoxy-4-methyl-2-cyclobutenols underwent efficient and very stereoselective tandem ring expansion-functionalizations in the presence of three different allylic chlorides and a catalyst system composed of 10% Hg(OCOCF3)(2) and 10% PdCl2. All products can be obtained with a stereoselectivity greater than 99:1 at the exocyclic alkene.

  DOI：

  10.1021/jo00084a038

文献信息

• Regiospecific synthesis of hydroxyquinones and related compounds from 3-tert-butoxycyclobutene-1,2-dione
  作者：Julia M. Heerding、Harold W. Moore

  DOI：10.1021/jo00012a046

  日期：1991.6
• HEERDING, JULIA M.;MOORE, HAROLD W., J. ORG. CHEM., 56,(1991) N2, C. 4008-4050
  作者：HEERDING, JULIA M.、MOORE, HAROLD W.

  DOI：——

  日期：——
• A method for the stereoselective construction of 4-alkoxy-5-alkylidenecyclopentenones by the tandem ring expansion-functionalization of 1-alkynylcyclobutenols using a palladium-mercury cocatalytic system
  作者：Lanny S. Liebeskind、Agnes Bombrun

  DOI：10.1021/jo00084a038

  日期：1994.3

  1-(1-Alkynyl)-4-methoxy-4-methyl-2-cyclobutenols, prepared by nucleophilic functionalization of cyclobutenediones, were transformed with high stereoselectivity into 4-methoxy-4-methyl-5-alkylidenecyclopentenones. The action of stoichiometric Hg(OCOCF3)(2) and then metathesis with NaCl produced 5-(1-(chloromercurio)alkylidene)-4-methoxy-4-methyl-2-cyclopentenones which were stereospecifically functionalized by palladium-mediated allylation and hydroxybutenylation. Treatment with Br-2/DMSO led to stereospecific bromodemercuration. The 1-(1-alkynyl)-4-methoxy-4-methyl-2-cyclobutenols underwent efficient and very stereoselective tandem ring expansion-functionalizations in the presence of three different allylic chlorides and a catalyst system composed of 10% Hg(OCOCF3)(2) and 10% PdCl2. All products can be obtained with a stereoselectivity greater than 99:1 at the exocyclic alkene.