8-<(4'S,2'E)-5'-(tert-Butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-5-hydroxy-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone | 165258-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-<(4'S,2'E)-5'-(tert-Butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-5-hydroxy-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone
• 英文别名: 2-trimethylsilylethyl N-[5-[(E,4S)-5-[tert-butyl(diphenyl)silyl]oxy-2,4-dimethylpent-2-enoyl]-8-hydroxy-6-methoxy-7-methyl-1,4-dioxonaphthalen-2-yl]carbamate
• CAS: 165258-16-2
• 化学式: C₄₁H₅₁NO₈Si₂
• 分子量: 742.029
• InChiKey: NLQDFTXUQOZIEN-CFDCUEGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.38
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-<(4'S,2'E)-5'-(tert-Butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-5-hydroxy-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone 、 sodium thiomethoxide 在 氧气 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以72%的产率得到8-<(4'S,2'E)-5'-(tert-Butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-5-hydroxy-7-methoxy-6-methyl-2-(methylthio)-3-carbonyl>amino>-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis of the Naphthoquinone Nucleus of Awamycin

  摘要：

  A synthesis of ketone 4, corresponding to the fully elaborated naphthoquinone nucleus of awamycin, is described. The synthesis involves the Diels-Alder reaction between diene 8 and quinone 9 to construct naphthoquinone 10, the coupling of bromide 15 and an ansa chain surrogate 17 via an aryllithium intermediate, and a late stage 1,4-addition of NaSMe to naphthoquinone 23 to afford the ketone 4.

  DOI：

  10.1021/jo00119a018
• 作为产物：
  描述：

  5-(Benzyloxy)-1,4,7-trimethoxy-6-methyl-3-naphthoic acid 在 palladium on activated charcoal 、 硫酸 吡啶 、 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 ammonium cerium(IV) nitrate 、 air 、 叠氮磷酸二苯酯 、 氢气 、 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 47.83h， 生成 8-<(4'S,2'E)-5'-(tert-Butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-5-hydroxy-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis of the Naphthoquinone Nucleus of Awamycin

  摘要：

  A synthesis of ketone 4, corresponding to the fully elaborated naphthoquinone nucleus of awamycin, is described. The synthesis involves the Diels-Alder reaction between diene 8 and quinone 9 to construct naphthoquinone 10, the coupling of bromide 15 and an ansa chain surrogate 17 via an aryllithium intermediate, and a late stage 1,4-addition of NaSMe to naphthoquinone 23 to afford the ketone 4.

  DOI：

  10.1021/jo00119a018

文献信息

• Synthesis of the Naphthoquinone Nucleus of Awamycin
  作者：William R. Roush、D. Scott Coffey

  DOI：10.1021/jo00119a018

  日期：1995.7

  A synthesis of ketone 4, corresponding to the fully elaborated naphthoquinone nucleus of awamycin, is described. The synthesis involves the Diels-Alder reaction between diene 8 and quinone 9 to construct naphthoquinone 10, the coupling of bromide 15 and an ansa chain surrogate 17 via an aryllithium intermediate, and a late stage 1,4-addition of NaSMe to naphthoquinone 23 to afford the ketone 4.