3-isopropoxy-2-phenyl-4-(N-phenylimino)cyclobut-2-en-1-one | 160386-91-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-isopropoxy-2-phenyl-4-(N-phenylimino)cyclobut-2-en-1-one
• 英文别名: 2-Phenyl-4-phenylimino-3-propan-2-yloxycyclobut-2-en-1-one
• CAS: 160386-91-4
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: ZGHUEQICCXRABE-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93 °C
• 沸点：
  456.9±55.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-isopropoxy-2-phenyl-4-(N-phenylimino)cyclobut-2-en-1-one 在 叔丁基锂 、 草酸 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：

  3,4-二异丙氧基-3-环丁烯-1,2-二酮 在 三氟乙酸酐 作用下， 生成 3-isopropoxy-2-phenyl-4-(N-phenylimino)cyclobut-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

文献信息

• 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。
• General Enantiospecific Route to Isochromanquinones. Synthesis of (-)-Nanaomycin D
  作者：Michael P. Winters、Michael Stranberg、Harold W. Moore

  DOI：10.1021/jo00104a004

  日期：1994.12

  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.