(+/-)-O-methylsterigmatocystin | 646060-09-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 杂色曲霉素
• 英文名称: (+/-)-O-methylsterigmatocystin
• 英文别名: Sterigmatocystin, O-methyl-(6CI)；11,15-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14(19),15,17-heptaen-13-one
• CAS: 646060-09-5
• 化学式: C₁₉H₁₄O₆
• 分子量: 338.317
• InChiKey: JKUJKKGMOZDDJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-O-methylsterigmatocystin 生成 黄曲霉毒素
  参考文献：
  名称：

  YABE, K.;ANDO, Y.;TERAKADO, N.;HASHIMOTO, J.;NAKAJIMA, H.;HAMASAKI, T., MYCOTOXINS AND PHYCOTOXINS88: COLLECT INVIT. PAP. 7TH INT. IUPAC SYMP., T+

  摘要：

  DOI：
• 作为产物：
  描述：

  6,8-Dimethoxy-2-phenylselanyl-1,2,3a,12c-tetrahydro-furo[3',2':4,5]furo[2,3-c]xanthen-7-one 在 4 Angstroem MS 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 (+/-)-O-methylsterigmatocystin
  参考文献：
  名称：

  Total Synthesis of O-Methylsterigmatocystin Using N-Alkylnitrilium Salts and Carbonyl−Alkene Interconversion in a New Xanthone Synthesis

  摘要：

  A general strategy is described for the preparation of substituted xanthones and embodied in the preparation of (+/-)-O-methylsterigmatocystin (OMST), the most advanced, known intermediate in the biosynthesis of aflatoxin. The essential features of this approach are the reaction of N-alkylnitrilium salts with activated aromatic rings, and protection of the derived xanthones as their corresponding alkenyl xanthenes. The latter are readily synthesized by reaction with n-butyllithium and dehydration. The resulting stabilization of the xanthone nucleus enables a wide range of chemical modification reactions to be carried out, and a facile and unusual cleavage of the alkene with peracid restores the desired xanthone. Compatibility of these operations with the preparation of the sensitive dihydrobisfuran is exemplified in the synthesis of OMST.

  DOI：

  10.1021/jo990099w

文献信息

• Total Synthesis of <i>O</i>-Methylsterigmatocystin Using <i>N</i>-Alkylnitrilium Salts and Carbonyl−Alkene Interconversion in a New Xanthone Synthesis
  作者：Linda K. Casillas、Craig A. Townsend

  DOI：10.1021/jo990099w

  日期：1999.5.1

  A general strategy is described for the preparation of substituted xanthones and embodied in the preparation of (+/-)-O-methylsterigmatocystin (OMST), the most advanced, known intermediate in the biosynthesis of aflatoxin. The essential features of this approach are the reaction of N-alkylnitrilium salts with activated aromatic rings, and protection of the derived xanthones as their corresponding alkenyl xanthenes. The latter are readily synthesized by reaction with n-butyllithium and dehydration. The resulting stabilization of the xanthone nucleus enables a wide range of chemical modification reactions to be carried out, and a facile and unusual cleavage of the alkene with peracid restores the desired xanthone. Compatibility of these operations with the preparation of the sensitive dihydrobisfuran is exemplified in the synthesis of OMST.
• YABE, K.;ANDO, Y.;TERAKADO, N.;HASHIMOTO, J.;NAKAJIMA, H.;HAMASAKI, T., MYCOTOXINS AND PHYCOTOXINS88: COLLECT INVIT. PAP. 7TH INT. IUPAC SYMP., T+
  作者：YABE, K.、ANDO, Y.、TERAKADO, N.、HASHIMOTO, J.、NAKAJIMA, H.、HAMASAKI, T.

  DOI：——

  日期：——