3-isopropoxy-4-phenylcyclobut-3-ene-1,2-dione | 114094-71-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-isopropoxy-4-phenylcyclobut-3-ene-1,2-dione
• 英文别名: 3-(1-methylethoxy)-4-phenyl-3-cyclobutene-1,2-dione；3-(1-methylethoxy)-4-phenylcyclobut-3-ene-1,2-dione；3-(1-methylethoxy)-4-phenyl-1,2-cyclobutenedione；3-isopropoxy-4-phenyl-3-cyclobutylene-1,2-dione；3-isopropoxy-4-phenyl-cyclobut-3-ene-1,2-dione；3-Phenyl-4-isopropoxy-3-cyclobutene-1,2-dione；3-Isopropoxy-4-phenyl-3-cyclobutene-1,2-dione；3-phenyl-4-propan-2-yloxycyclobut-3-ene-1,2-dione
• CAS: 114094-71-2
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: DJHMBVFWUYOHEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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-isopropoxy-4-phenylcyclobut-3-ene-1,2-dione 在 叔丁基锂 、 草酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 4-[(3aS,5S,7aS)-5-methyl-2-tri(propan-2-yl)silyloxy-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-7-yl]-4-hydroxy-3-phenyl-2-propan-2-yloxycyclobut-2-en-1-one
  参考文献：
  名称：

  General Enantiospecific Route to Isochromanquinones. Synthesis of (-)-Nanaomycin D

  摘要：

  A general enantiospecific synthesis of isochromanquinones is presented. This entails an efficient synthesis of (3aS, 5S, 7aR)-7-bromo-3,3a,5,7a-tetrahydro-5-methyl-2H-furo[3,2-b]pyran-2-one (12) and ultimately the lithium agent 15 from commercially available L-rhamnose. Addition of 15 to the appropriate cyclobutenedione followed by thermolysis of the resulting cyclobutenone leads to the isochromanquinones 16a-c. In an analogous fashion the naturally occurring product, (-)-nanaomycin D, was synthesized. In addition, new methodology involving the ring expansion of iminocyclobutenones to aminophenols was discovered.

  DOI：

  10.1021/jo00104a004
• 作为产物：
  描述：

  2,3-bis(1-methylethoxy)-4-hydroxy-4-phenylcyclobut-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3-isopropoxy-4-phenylcyclobut-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

• Titanium-mediated olefinations of cyclobutenedione derivatives
  作者：Nicos A Petasis、Yong-Han Hu、Dian-Kui Fu

  DOI：10.1016/0040-4039(95)01186-l

  日期：1995.8

  A variety of cyclobutenedione derivatives, including squaric esters, react with dimethyl titanocene to afford the corresponding methylenation products. With certain mixed-substituted substrates the reaction proceeds preferably at a ketonic carbonyl rather than a vinylogous ester.

  各种环丁烯二酮衍生物（包括方酸酯）与二甲基钛茂反应，得到相应的亚甲基化产物。对于某些混合取代的底物，反应优选在酮羰基而不是乙烯基酯上进行。
• 4-Iminocyclobutenones: Synthesis and Building-Blocks of Aminohydroquinones and Annulated Quinolines
  作者：Ernst Schaumann、Gerrit Oppermann、Michael Stranberg、Harold Moore、Gunadi Adiwidjaja

  DOI：10.1055/s-0029-1218767

  日期：2010.6

  Two methods are presented for the synthesis of the title compounds starting from cyclobutenediones: an alkoxide substitution approach and a Staudinger reaction. Unsaturated lithiumorganyls may be added to the remaining carbonyl group and on heating lead to ring enlargement in a cascading process. 4-Alkenyl or 4-aryl derivatives yield aminophenols or -naphthols; 4-alkynyl compounds give cyclopenta-annulated quinolines.

  本文介绍了从环丁烯二酮出发合成标题化合物的两种方法：烷氧化物取代法和施陶丁格反应。不饱和的锂有机物可以添加到剩余的羰基上，加热后通过级联过程导致环扩大。4-烯基或4-芳基衍生物产生氨基苯酚或氨基萘酚；4-炔基化合物则生成环戊稠合的喹啉。
• New Syntheses and Ring Expansion Reactions of Cyclobutenimines
  作者：Ernst Schaumann、Gerrit Oppermann、Michael Stranberg、Harold W. Moore

  DOI：10.1071/ch10318

  日期：——

  cyclobutenediones and an aza-Wittig method. A new synthetic route to N-alkyl derivatives is also presented. This involves O-alkylation of 3-alkylamino-1,2-cyclobutenediones using Meerwein’s reagent and subsequent deprotonation under non-hydrolytic conditions. Lithium organyls were found to add to the remaining carbonyl group. The resulting tertiary alcohols undergo ring enlargement on heating in xylene to give

  据报道，具有N-（杂）芳基取代的亚氨基环丁烯酮的合成有两种途径：以环丁二烯为起始的加成/取代序列和aza-Wittig方法。还提出了合成N-烷基衍生物的新途径。这涉及使用Meerwein试剂对3-烷基氨基-1,2-环丁二烯进行O-烷基化，然后在非水解条件下进行去质子化。发现锂有机基团加到剩余的羰基上。生成的叔醇在二甲苯中加热后进行扩环反应，分别从4-乙烯基，4-芳基和4-炔基衍生物得到4-氨基苯酚，4-氨基-1-萘酚或环戊基环化的喹啉。
• Synthesis of substituted cyclobutenediones by the palladium catalyzed cross-coupling of halocyclobutenediones with organostannanes.
  作者：Lanny S. Liebeskind、Jianying Wang

  DOI：10.1016/s0040-4039(00)97604-4

  日期：1990.1

  Halo-substituted cyclobutenediones undergo palladium catalyzed cross-coupling with organostannanes providing a mild method for the synthesis of substituted cyclobutenediones.

  卤代取代的环丁烯二酮经历钯催化与有机锡的交叉偶联，为合成取代的环丁烯二酮提供了温和的方法。
• 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。