5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone | 165258-15-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-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]-6-methoxy-7-methyl-1,4-dioxo-8-phenylmethoxynaphthalen-2-yl]carbamate
• CAS: 165258-15-1
• 化学式: C₄₈H₅₇NO₈Si₂
• 分子量: 832.153
• InChiKey: REFMAVVTGJBYNR-IMLWDQESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.25
• 重原子数：
  59
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone 在 palladium on activated charcoal air 、 氢气 作用下， 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
• 作为产物：
  描述：

  5-(Benzyloxy)-1,4,7-trimethoxy-6-methyl-3-naphthoic acid 在 硫酸 吡啶 、 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 ammonium cerium(IV) nitrate 、 叠氮磷酸二苯酯 、 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 44.33h， 生成 5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-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.