rubroflavin | 138749-63-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: rubroflavin
• 英文别名: [(Z)-[2-methylsulfanyl-6-[(S)-methylsulfinyl]-4-oxocyclohexa-2,5-dien-1-ylidene]amino]urea
• CAS: 138749-63-0
• 化学式: C₉H₁₁N₃O₃S₂
• 分子量: 273.337
• InChiKey: UWVQDKLIYCMDDV-NLZINVLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  rubroflavin 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以45%的产率得到oxyrubroflavin
  参考文献：
  名称：

  Pigments from the Puffball Calvatia rubro-flava − Isolation, Structural Elucidation and Synthesis

  摘要：

  The orange pigment rubroflavin (1) from the dried fruit bodies of Calvatia rubro-flava (Lycoperdaceae) owes its high optical rotation to a methanesulfinyl group directly attached to a 1,4-benzoquinone semicarbazone chromophore. Rubroflavin is present in fresh fungi in its leuco form 4, which is easily oxidized to 1. Thermal fragmentation of 1 yields (-)-3-methanesulfinyl-5-(methylthio)phenol (6), whose configuration was assigned as (S) by quantum mechanical calculations. This result is supported by CD comparison of 6 with (S)-4-(methanesulfinyl) toluene, and the synthesis of (S)-1 from esters of deoxyrubroflavin (8) by stereoselective sulfoxidation. In the same manner, optically active (S,S)-oxyrubroflavin (2) and (S)-craniformin (3) were obtained. NMR measurements in different solvents indicate that 1 and the related 1,4-benzoquinone semicarbazones are in equilibrium with their azophenol tautomers.

  DOI：

  10.1002/1099-0690(200108)2001:16<3097::aid-ejoc3097>3.0.co;2-v
• 作为产物：
  描述：

  deoxyrubroflavin 在 titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 sodium hydroxide 、 D-(-)-酒石酸二乙酯 、 水 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 rubroflavin
  参考文献：
  名称：

  Pigments from the Puffball Calvatia rubro-flava − Isolation, Structural Elucidation and Synthesis

  摘要：

  The orange pigment rubroflavin (1) from the dried fruit bodies of Calvatia rubro-flava (Lycoperdaceae) owes its high optical rotation to a methanesulfinyl group directly attached to a 1,4-benzoquinone semicarbazone chromophore. Rubroflavin is present in fresh fungi in its leuco form 4, which is easily oxidized to 1. Thermal fragmentation of 1 yields (-)-3-methanesulfinyl-5-(methylthio)phenol (6), whose configuration was assigned as (S) by quantum mechanical calculations. This result is supported by CD comparison of 6 with (S)-4-(methanesulfinyl) toluene, and the synthesis of (S)-1 from esters of deoxyrubroflavin (8) by stereoselective sulfoxidation. In the same manner, optically active (S,S)-oxyrubroflavin (2) and (S)-craniformin (3) were obtained. NMR measurements in different solvents indicate that 1 and the related 1,4-benzoquinone semicarbazones are in equilibrium with their azophenol tautomers.

  DOI：

  10.1002/1099-0690(200108)2001:16<3097::aid-ejoc3097>3.0.co;2-v

文献信息

• Pigments from the Puffball Calvatia rubro-flava − Isolation, Structural Elucidation and Synthesis
  作者：Burkhard Fugmann、Siegbert Arnold、Wolfgang Steglich、Jörg Fleischhauer、Charlotte Repges、Axel Koslowski、Gerhard Raabe

  DOI：10.1002/1099-0690(200108)2001:16<3097::aid-ejoc3097>3.0.co;2-v

  日期：2001.8

  The orange pigment rubroflavin (1) from the dried fruit bodies of Calvatia rubro-flava (Lycoperdaceae) owes its high optical rotation to a methanesulfinyl group directly attached to a 1,4-benzoquinone semicarbazone chromophore. Rubroflavin is present in fresh fungi in its leuco form 4, which is easily oxidized to 1. Thermal fragmentation of 1 yields (-)-3-methanesulfinyl-5-(methylthio)phenol (6), whose configuration was assigned as (S) by quantum mechanical calculations. This result is supported by CD comparison of 6 with (S)-4-(methanesulfinyl) toluene, and the synthesis of (S)-1 from esters of deoxyrubroflavin (8) by stereoselective sulfoxidation. In the same manner, optically active (S,S)-oxyrubroflavin (2) and (S)-craniformin (3) were obtained. NMR measurements in different solvents indicate that 1 and the related 1,4-benzoquinone semicarbazones are in equilibrium with their azophenol tautomers.