1,1-dimethylethyl 3,4-dioxo-α-methyl-2-(1-methylethoxy)-1-cyclobutene-1-acetate | 253353-07-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-dimethylethyl 3,4-dioxo-α-methyl-2-(1-methylethoxy)-1-cyclobutene-1-acetate
• 英文别名: Tert-butyl 2-(3,4-dioxo-2-propan-2-yloxycyclobuten-1-yl)propanoate；tert-butyl 2-(3,4-dioxo-2-propan-2-yloxycyclobuten-1-yl)propanoate
• CAS: 253353-07-0
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: HCAASHOMEYHPSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl 3,4-dioxo-α-methyl-2-(1-methylethoxy)-1-cyclobutene-1-acetate 在 三氟乙酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.25h， 以57%的产率得到4-Ethyl-3-isopropoxy-3-cyclobuten-1,2-dion
  参考文献：
  名称：

  Efficient Synthesis of a Novel 4-Hydroxy-2,3-dioxocyclobut-1-enyl Group Containing Amino Acids

  摘要：

  [GRAPHICS]Syntheses of novel amino acids possessing a squaryl group, 1-3, in an optically active form are described. The syntheses of 1-3 were conducted by a concise route involving (1) an aldol addition of an enolate derived from Gly, L-Asp, or L-Glu to diisopropyl squarate (4) and (2) an efficient decarboxylation of the aldol adducts based on the electron-withdrawing property of the squaryl group. Introducing N-protected group to 2 and 3 and peptide formation reactions are also described.

  DOI：

  10.1021/ol990286g
• 作为产物：
  描述：

  丙酸叔丁酯 在 盐酸 、 cerium(III) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 1,1-dimethylethyl 3,4-dioxo-α-methyl-2-(1-methylethoxy)-1-cyclobutene-1-acetate
  参考文献：
  名称：

  Efficient Synthesis of a Novel 4-Hydroxy-2,3-dioxocyclobut-1-enyl Group Containing Amino Acids

  摘要：

  [GRAPHICS]Syntheses of novel amino acids possessing a squaryl group, 1-3, in an optically active form are described. The syntheses of 1-3 were conducted by a concise route involving (1) an aldol addition of an enolate derived from Gly, L-Asp, or L-Glu to diisopropyl squarate (4) and (2) an efficient decarboxylation of the aldol adducts based on the electron-withdrawing property of the squaryl group. Introducing N-protected group to 2 and 3 and peptide formation reactions are also described.

  DOI：

  10.1021/ol990286g

文献信息

• Efficient Synthesis of a Novel 4-Hydroxy-2,3-dioxocyclobut-1-enyl Group Containing Amino Acids
  作者：Tetsuro Shinada、Ken-ichi Hayashi、Toshihiro Hayashi、Yasutaka Yoshida、Manabu Horikawa、Keiko Shimamoto、Yasushi Shigeri、Noboru Yumoto、Yasufumi Ohfune

  DOI：10.1021/ol990286g

  日期：1999.11.1

  [GRAPHICS]Syntheses of novel amino acids possessing a squaryl group, 1-3, in an optically active form are described. The syntheses of 1-3 were conducted by a concise route involving (1) an aldol addition of an enolate derived from Gly, L-Asp, or L-Glu to diisopropyl squarate (4) and (2) an efficient decarboxylation of the aldol adducts based on the electron-withdrawing property of the squaryl group. Introducing N-protected group to 2 and 3 and peptide formation reactions are also described.