1,1-dimethylethyl 3,4-dioxo-2-(1-methylethoxy)-1-cyclobutene-1-acetate | 196790-38-2

• 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-2-(1-methylethoxy)-1-cyclobutene-1-acetate
• 英文别名: Tert-butyl 2-(3,4-dioxo-2-propan-2-yloxycyclobuten-1-yl)acetate
• CAS: 196790-38-2
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: ZIELQQDUJADHSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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-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59%的产率得到3-(1-methylethoxy)-4-methylcyclobut-3-ene-1,2-dione
  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：

  (叔丁氧基羰基亚甲基)三苯基磷烷 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 1,1-dimethylethyl 3,4-dioxo-2-(1-methylethoxy)-1-cyclobutene-1-acetate
  参考文献：
  名称：

  wittig和霍纳-埃蒙斯反应对二烷基二烯烃的烯烃进行烯烃化。轻松合成3,4-二氧羰基-1-环丁烯-1-乙酸酯

  摘要：

  将二烷基季铵盐1-5与数个烷基化物6和膦酸酯7进行烯烃化反应，得到相应的亚烷基产物8-12。在霍纳-埃蒙斯反应的情况下，观察到Z-亚烷基产物的立体选择性形成。酸催化的8-12水解产生了方酸乙酸酯13。

  DOI：

  10.1016/s0040-4039(97)01656-0

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.
• Olefination of dialkyl squarates by wittig and horner-emmons reactions. A facile synthesis of 3,4-dioxo-1-cyclobutene-1-acetic acid esters
  作者：Ken-ichi Hayashi、Tetsuro Shinada、Kazuhiko Sakaguchi、Manabu Horikawa、Yasufumi Ohfune

  DOI：10.1016/s0040-4039(97)01656-0

  日期：1997.10

  Olefination of dialkyl squarates 1–5 with several ylides 6 and phosphonates 7 gave the corresponding alkylidene products 8–12. In the case of Horner-Emmons reactions, stereoselective formation of Z-alkylidene products was observed. An acid-catalyzed hydrolysis of 8–12 gave squarylacetic acid esters 13.

  将二烷基季铵盐1-5与数个烷基化物6和膦酸酯7进行烯烃化反应，得到相应的亚烷基产物8-12。在霍纳-埃蒙斯反应的情况下，观察到Z-亚烷基产物的立体选择性形成。酸催化的8-12水解产生了方酸乙酸酯13。