2-[2,5-dihydroxy-4-(3-methylbut-3-en-1-ynyl)phenyl]acetic acid methyl ester | 1071817-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[2,5-dihydroxy-4-(3-methylbut-3-en-1-ynyl)phenyl]acetic acid methyl ester
• 英文别名: Methyl 2-[2,5-dihydroxy-4-(3-methylbut-3-en-1-ynyl)phenyl]acetate
• CAS: 1071817-60-1
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: MAPSCXQSSMVZEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2,5-dihydroxy-4-(3-methylbut-3-en-1-ynyl)phenyl]acetic acid methyl ester 、 叔丁基二甲基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以90%的产率得到[2,5-bis[(tert-butyldimethylsilyl)oxy]-4-(3-methylbut-3-en-1-ynyl)phenyl]acetic acid methyl ester
  参考文献：
  名称：

  A Route to 1,4-Disubstituted Aromatics and Its Application to the Synthesis of the Antibiotic Culpin

  摘要：

  A method is described for converting tert-butyl benzoates or tert-butyl 1-naphthoates into derivatives having an alkyl or substituted alkyl group in a 1,4-relationship to an alkyl, aryl, alkenyl, or alkynyl group. Key steps in the sequence are (i) addition of an organometallic species to a cross-conjugated cyclohexadienone obtained by Birch alkylation of a tert-butyl benzoate or a tert-butyl 1-naphthoate, followed by allylic oxidation, and (ii) treatment with BiCl3 center dot H2O, which results in removal of the tertbutyl group and spontaneous decarboxylative aromatization. The method was applied to the synthesis of the antimicrobial fungal metabolite culpin.

  DOI：

  10.1021/jo8015192
• 作为产物：
  描述：

  tert-butyl 4-hydroxy-1-[(methoxycarbonyl)methyl]-2,5-bis(methoxymethoxy)-4-(3-methylbut-3-en-1-ynyl)cyclohexa-2,5-dienecarboxylate 在 H₂O*BiCl₃ 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以82.9 mg的产率得到2-[2,5-dihydroxy-4-(3-methylbut-3-en-1-ynyl)phenyl]acetic acid methyl ester
  参考文献：
  名称：

  A Route to 1,4-Disubstituted Aromatics and Its Application to the Synthesis of the Antibiotic Culpin

  摘要：

  A method is described for converting tert-butyl benzoates or tert-butyl 1-naphthoates into derivatives having an alkyl or substituted alkyl group in a 1,4-relationship to an alkyl, aryl, alkenyl, or alkynyl group. Key steps in the sequence are (i) addition of an organometallic species to a cross-conjugated cyclohexadienone obtained by Birch alkylation of a tert-butyl benzoate or a tert-butyl 1-naphthoate, followed by allylic oxidation, and (ii) treatment with BiCl3 center dot H2O, which results in removal of the tertbutyl group and spontaneous decarboxylative aromatization. The method was applied to the synthesis of the antimicrobial fungal metabolite culpin.

  DOI：

  10.1021/jo8015192

文献信息

• A Route to 1,4-Disubstituted Aromatics and Its Application to the Synthesis of the Antibiotic Culpin
  作者：Rajesh Sunasee、Derrick L. J. Clive

  DOI：10.1021/jo8015192

  日期：2008.10.17

  A method is described for converting tert-butyl benzoates or tert-butyl 1-naphthoates into derivatives having an alkyl or substituted alkyl group in a 1,4-relationship to an alkyl, aryl, alkenyl, or alkynyl group. Key steps in the sequence are (i) addition of an organometallic species to a cross-conjugated cyclohexadienone obtained by Birch alkylation of a tert-butyl benzoate or a tert-butyl 1-naphthoate, followed by allylic oxidation, and (ii) treatment with BiCl3 center dot H2O, which results in removal of the tertbutyl group and spontaneous decarboxylative aromatization. The method was applied to the synthesis of the antimicrobial fungal metabolite culpin.