摩熵化学
数据库官网
小程序
打开微信扫一扫
首页 分子通 化学资讯 化学百科 反应查询 关于我们
请输入关键词

(+/-)-O-methylsterigmatocystin hydrate | 30099-66-2

中文名称
——
中文别名
——
英文名称
(+/-)-O-methylsterigmatocystin hydrate
英文别名
Dihydrohydroxy-O-methylsterigmatocystin;5-hydroxy-11,15-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,9,11,14(19),15,17-hexaen-13-one
(+/-)-O-methylsterigmatocystin hydrate化学式
CAS
30099-66-2
化学式
C19H16O7
mdl
——
分子量
356.332
InChiKey
ATDWDHGTLHHXNU-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.3
  • 重原子数:
    26
  • 可旋转键数:
    2
  • 环数:
    5.0
  • sp3杂化的碳原子比例:
    0.32
  • 拓扑面积:
    83.4
  • 氢给体数:
    1
  • 氢受体数:
    7

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
    —— (+/-)-O-methylsterigmatocystin 646060-09-5 C19H14O6 338.317

反应信息

  • 作为反应物:
    描述:
    (+/-)-O-methylsterigmatocystin hydrate 在 Amberlyst 15 、 4 Angstroem MS 、 间氯过氧苯甲酸 作用下, 以 二氯甲烷乙腈 为溶剂, 反应 72.33h, 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
  • 作为产物:
    描述:
    (5,7-Dimethoxy-6-oxo-2-triisopropylsilanyloxy-1,2-dihydro-6H-3,11-dioxa-cyclopenta[a]anthracen-1-yl)-acetaldehyde 在 triethylamine tris(hydrogen fluoride) 作用下, 以 二氯甲烷乙腈 为溶剂, 反应 8.5h, 以88%的产率得到(+/-)-O-methylsterigmatocystin hydrate
    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
点击查看最新优质反应信息

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.
查看更多

同类化合物

原乙酰基杂色曲霉毒素 O-甲基柄曲菌素 8-羟基-6-甲氧基-1,2,3aR,12cS-四氢-7H-呋喃并(3',2':4,5)呋喃并(2,3-c)氧杂蒽-7-酮 5-甲氧基柄曲霉素 5,6-二甲氧基杂色曲霉毒素 1,2-二氢-O-甲基杂色曲霉毒素 1,2,3a,12c-四氢-8-羟基-6-甲氧基-7H-呋喃并[3',2':4,5]呋喃并[2,3-c]氧杂蒽-7-酮乙酸盐 (3aR,12cS)-6,8-二羟基-3a,12c-二氢-7H-呋喃并[3',2':4,5]呋喃并[2,3-c]氧杂蒽-7-酮 (3aR,12cS)-3a,12c-二氢-6,8-二羟基-7H-呋喃并[3',2':4,5]呋喃并[2,3-c]氧杂蒽-7-酮二乙酸酯 (-)-1,2,3a,12c-四氢-6,8-二羟基-7H-呋喃并(3',2':4,5)呋喃并(2,3-c)氧杂蒽-7-酮 Sterigmatocystin 2,11-dihydroxy-6,8-dimethoxy-7H-1,2-dihydrofuro[2','3:4,5]furo[2,3-c]-xanthen-7-one 7H-Furo(3',2':4,5)furo(2,3-c)xanthen-7-one, 3a,12c-dihydro-8-hydroxy-6,10,11-trimethoxy-, (3aR-cis)- dihydro-O-methylsterigmatocystin Dihydromethylsterigmatocystin (3S,7S)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one Sterigmatocystin, TBDMS derivative 15-Hydroxy-10,11-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1(12),2(9),4,10,14,16,18-heptaen-13-one 6H-Purin-6-one, 2-amino-1,9-dihydro-9-(1,2,3a,12c-tetrahydro-1,8-dihydroxy-6-methoxy-7-oxo-7H-furo(3',2':4,5)furo(2,3-c)xanthen-2-yl)-, (1R-(1alpha,2beta,3aalpha,12calpha))- 16-Hydroxy-12-methoxy-5,7,9,21-tetraoxahexacyclo[11.8.0.02,10.03,8.04,6.015,20]henicosa-1,10,12,15,17,19-hexaen-14-one (3R,7S)-15-hydroxy-11,18-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one (3R,7R)-15-hydroxy-11,18-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one (3S,7S)-15-hydroxy-11,18-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one 7H-Xantheno[3,4-b]furo[3,2-d]furan, 3a,12b-dihydro-6-methoxy-7-oxo-8-(trimethylsilyloxy)- 11-Hydroxy-15-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1(12),2(9),10,14(19),15,17-hexaen-13-one 6-Methoxy-sterigmatocystin 6,8-dihydroxy-1,2,3a,12c-tetrahydrofuro[2,3-c]furoxanth-7-one Hydroxydihydrosterigmatocystin (15-Hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,9,11,14,16,18-hexaen-5-yl) acetate 5,6-Dimethoxydihydrosterigmatocycstin sterigmatocystin De-O-methylsterigmatocystin 5-Methoxydihydrosterigmatocystin Aspertoxin (15-Hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,9,11,14,16,18-hexaen-5-yl) 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate 15-Hydroxy-5,11,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,9,11,14,16,18-hexaen-13-one 11-Hydroxy-15-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1(12),2(9),4,10,14(19),15,17-heptaen-13-one 15-Hydroxy-5,11-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,9,11,14,16,18-hexaen-13-one 11-(3,4-Dihydroxy-5-methoxyoxan-2-yl)oxy-15-hydroxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one 10,15-Dihydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1(12),2(9),10,14,16,18-hexaen-13-one 15,18-Dihydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one 7H-Furo(3',2':4,5)furo(2,3-c)xanthen-7-one, 2-(acetyloxy)-1,2,3a,12c-tetrahydro-8-hydroxy-6-methoxy- (+/-)-O-methylsterigmatocystin hydrate 5-Methoxysterigmatocystin; 7-Hydroxy-6,10-dimethoxydifuroxanthone; 5-MS (+/-)-O-methylsterigmatocystin