3-Bromo-5-hydroxy-7-methoxymethoxy-2,6-dimethyl-[1,4]naphthoquinone | 85954-41-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-Bromo-5-hydroxy-7-methoxymethoxy-2,6-dimethyl-[1,4]naphthoquinone
• 英文别名: 3-Bromo-5-hydroxy-7-(methoxymethoxy)-2,6-dimethylnaphthalene-1,4-dione
• CAS: 85954-41-2
• 化学式: C₁₄H₁₃BrO₅
• 分子量: 341.158
• InChiKey: WBCKOVHIWJFVGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Bromo-5-hydroxy-7-methoxymethoxy-2,6-dimethyl-[1,4]naphthoquinone 在 sodium hydroxide 、 sodium tetrahydroborate 、 正丁基锂 、 cerium(III) chloride 、 silver(l) oxide 作用下， 以 1,4-二氧六环 、 氯仿 、 水 为溶剂， 生成 1,4-dimethoxy-6-(methoxymethoxy)-3,7-dimethyl-8-phenylmethoxynaphthalene-2-carboxylic acid
  参考文献：
  名称：

  合成链霉菌素D：合成完整的芳香族前体并与ansa链片段偶联

  摘要：

  高度官能化链菌素- damavaricin d芳香族前体12和15已经制备并与丙醛或不饱和醛16和18通过芳基锂中间体，得到2，3和19。

  DOI：

  10.1016/0040-4039(93)85004-g
• 作为产物：
  描述：

  二甲醇缩甲醛 、 3-Bromo-5,7-dihydroxy-2,6-dimethyl-[1,4]naphthoquinone 在 phosphorus pentoxide 作用下， 以 氯仿 为溶剂， 以97%的产率得到3-Bromo-5-hydroxy-7-methoxymethoxy-2,6-dimethyl-[1,4]naphthoquinone
  参考文献：
  名称：

  合成链霉菌素D：合成完整的芳香族前体并与ansa链片段偶联

  摘要：

  高度官能化链菌素- damavaricin d芳香族前体12和15已经制备并与丙醛或不饱和醛16和18通过芳基锂中间体，得到2，3和19。

  DOI：

  10.1016/0040-4039(93)85004-g

文献信息

• Synthesis of highly functionalized naphthoate precursors to damavaricin D — Observation of kinetically stable benzocyclohexadienones in the bromination reactions of highly functionalized β-naphthol derivatives
  作者：William R. Roush、David J. Madar、D. Scott Coffey

  DOI：10.1139/cjc-79-11-1711

  日期：——

  Selective syntheses of the highly substituted bromonaphthoates 4a, 4b, 19, and 22 are reported. These compounds were targeted as precursors to the naphthoquinone nucleus of damavaricin D; compound 22 ultimately was used in the successful total synthesis. The synthesis of 22 features the Diels-Alder reaction of the oxygenated diene 5 and 2,6-dibromo-3-methylbenzoquinone 6 to establish the core naphthalenic unit. The quinone was protected throughout this synthesis as a 1,4-bis-methoxymethyl-1,4-dihydroquinone (see 36). The C-2-carboalkoxy group of 22 was added by carboxylation of the aryllithium intermediate generated from 36, and protected as a beta -trimethylsilylethyl ester. Finally, the C-8-Br substituent was introduced by NBS bromination of 38. This reaction proceeds by way of bromobenzocyclohexadienone 39. Related bromobenzo-cyclohexadienones 13 and 29 were observed in the NBS brominations of the highly functionalized beta -naphthyl MOM ethers 11 and 28. The bromobenzocyclohexadienones 29 and 39 undergo facile substitution reactions with chloride ion and reduction with bromide ion at rates competitive with base-promoted aromatization. The surprising kinetic stability of these intermediates is attributed to a combination of steric and stereoelectronic factors.
• A synthesis of the naphthalene core of streptovaricin D via A synthon of NH2+
  作者：Barry M. Trost、William H. Pearson

  DOI：10.1016/s0040-4039(00)81382-9

  日期：1983.1