4-n-butyl-3-(1-methylethoxy)cyclobut-3-ene-1,2-dione | 114094-70-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-n-butyl-3-(1-methylethoxy)cyclobut-3-ene-1,2-dione
• 英文别名: 3-Isopropoxy-4-n-butyl-3-cyclobutene-1,2-dione；3-n-Butyl-4-isopropoxy-3-cyclobutene-1,2-dione；3-butyl-4-isopropoxy-cyclobut-3-ene-1,2-dione；4-butyl-3-isopropoxycyclobut-3-ene-1,2-dione；2-butyl-3-isopropoxy cyclobutenedione；3-butyl-4-isopropoxycyclobutenedione；3-Butyl-4-propan-2-yloxycyclobut-3-ene-1,2-dione
• CAS: 114094-70-1
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: HKKUKXJOFCQNTD-UHFFFAOYSA-N

物化性质

• 沸点：
  294.1±50.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  4-n-butyl-3-(1-methylethoxy)cyclobut-3-ene-1,2-dione 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以81%的产率得到2-n-Butyl-4-hydroxy-2-cyclobuten-1-one
  参考文献：
  名称：

  A general, regioselective synthesis of substituted benzocyclobutenedione monoacetals

  摘要：

  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.

  DOI：

  10.1021/jo00067a029
• 作为产物：
  描述：

  2,3-bis(1-methylethoxy)-4-n-butyl-4-hydroxycyclobut-2-en-1-one 在 盐酸 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以65%的产率得到4-n-butyl-3-(1-methylethoxy)cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  方酸衍生物的无水质子电导率。

  摘要：

  在本文中，我们介绍了方酸衍生物作为无水质子导体。我们报告了四种方酸衍生物的合成，表征和质子电导率。一种衍生物的无水质子电导率在110摄氏度下为2.3 x 10（-3）S cm（-1），与熔融的1H-1,2,3-三唑或1H-咪唑的电导率相当。

  DOI：

  10.1039/c2cc31283b

文献信息

• Synthesis of alkyl substituted cyclobutenediones by free radical chemistry. Carbon for nitrogen replacement in the α-Amino acid Bioisostere -- 34-Diamino-3-cyclobutene-1,2-dione.
  作者：William A. Kinney

  DOI：10.1016/s0040-4039(00)73543-x

  日期：1993.4

  A novel free radical method for the synthesis of alkyl substituted cyclobutenediones was demonstrated, allowing for incorporation of a variety of functionalities. The synthesis of an analog of NMDA antagonist 1 was thereby facilitated.

  证明了一种新颖的自由基方法，用于合成烷基取代的环丁二烯，可结合多种功能。从而促进了NMDA拮抗剂1的类似物的合成。
• An expedient approach to synthesize fluorescent 3-substituted 4H-quinolizin-4-ones via (η⁴-vinylketene)-Fe(CO)₃ complexes
  作者：Alfredo Rosas-Sánchez、Rubén A. Toscano、José G. López-Cortés、M. Carmen Ortega-Alfaro

  DOI：10.1039/c4dt03021d

  日期：——

  From simple starting materials, an efficient methodology for the synthesis of 3-substituted 4H-quinolizin-4-ones using (η⁴-vinylketene)-Fe(CO)₃ complexes as key intermediates was developed. Fluorescent properties and quantum yields were determined.

  从简单的起始材料出发，开发了一种合成3-取代的4H-喹啉-4-酮的高效方法，其中以(η4-乙烯酮)-Fe(CO)3复合物作为关键中间体。测定了荧光性质和量子产率。
• TFA-catalyzed ring transformation of 4-hydroxycyclobutenone: A simple and general route for preparation of 3-substituted 4-aminofuran-2(5H )-ones †
  作者：Jie Wang、Xin Jiang、Ming Chen、Zongming Ge、Yuefei Hu、Hongwen Hu

  DOI：10.1039/b004654j

  日期：——

  positions, respectively, to yield 4-substituted 3-aminocyclobutene-1,2-diones 14. Reduction of compounds 14 with NaBH4 yield 2-substituted 3-amino-4-hydroxycyclobutenones 15 in high yields. By ring transformation of products 15 catalyzed by TFA, a simple and general route for the preparation of 3-substituted 4-aminofuran-2(5H)-ones 4 is developed. A two-step mechanism is proposed to describe the ring

  按照3,4-二异丙氧基环丁烯-1,2-二酮11的烷基化和胺化的便利顺序，可以轻松地实现三个典型的取代基（H，n-Bu和Ph）和三个典型的氨基（未取代，伯和仲）分别引入其C-3和C-4位置，以产生4-取代的3-氨基环丁烯-1,2-二酮14。用NaBH 4还原化合物14可高产率地产生2-取代的3-氨基-4-羟基环丁烯酮15。通过TFA催化的产物15的环转化，是制备3-取代的4-氨基呋喃-2（5 H）-ones 4的简单且通用的方法4被开发。提出了两步机制来描述烯酮15的环转化。实验结果表明，对二甲苯的回流过程对于15的初始热电开环以产生中间体羟基烯酮16a和16b至关重要。然后将它们在TFA存在下内酯化，以51-94％的收率得到呋喃酮4。
• Highly Regioselective Monothionation of Squaric and Semisquaric Acid Derivatives
  作者：Martin Müller、Matthew J. Heileman、Harold W. Moore、Ernst Schaumann、Gunadi Adiwidjaja

  DOI：10.1055/s-1997-1496

  日期：1997.1

  An efficient synthesis of 4-thioxocyclobut-2-enones by the action of 0.5 molar equivalents of Lawesson’s reagent on the corresponding diones is reported.

  报告中介绍了通过 0.5 摩尔当量的劳森试剂作用于相应的二酮，高效合成 4-硫酮环丁烷-2-烯酮的方法。
• Nickel-catalyzed ring-opening of α-hydroxycyclobutenones with a remarkable ligand effect
  作者：Songsong Gao、Xiangdong Hu

  DOI：10.1039/c7cc03340k

  日期：——

  A Ni-catalyzed ring-opening of α-hydroxycyclobutenones is reported herein. A remarkable ligand effect was observed during transformations following the ring-opening. The employment of PPh3 leads to the formation of 2-furanones 2 through a migration of an alkoxyl group, and 2-furanones 3 were generated through a migration of hydrogen in the presence of Xantphos, affording a divergent approach to 2-furanones

  本文报道了Ni催化的α-羟基环丁烯酮的开环。开环后的转化过程中观察到了显着的配体效应。PPh3的使用通过烷氧基的迁移导致形成2-呋喃酮2，而在Xantphos的存在下通过氢的迁移生成了2-呋喃酮3，从而提供了一种具有多种功能的2-呋喃酮的发散方法。组。