Ethyl 4-(benzenesulfinyl)-1-hydroxy-3-methylnaphthalene-2-carboxylate | 169216-79-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Ethyl 4-(benzenesulfinyl)-1-hydroxy-3-methylnaphthalene-2-carboxylate
• CAS: 169216-79-9
• 化学式: C₂₀H₁₈O₄S
• 分子量: 354.427
• InChiKey: HQDISAPNYDBARA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  82.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 4-(benzenesulfinyl)-1-hydroxy-3-methylnaphthalene-2-carboxylate 在 manganese(IV) oxide 、 三氟乙酸酐 作用下， 生成 3-methyl-1,4-dioxo-1,4-dihydro-[2]naphthoic acid ethyl ester
  参考文献：
  名称：

  An efficient synthesis of p-quinones utilizing a novel Pummerer-type rearrangement of p-sulfinylphenols

  摘要：

  对亚磺酰基苯酚衍生物 1 和 5 经三氟乙酸酐处理后，会在芳香环上发生普默尔型重排反应，同时发生脱硫反应，从而得到 1 : 1 的相应对醌和对二氢醌混合物。

  DOI：

  10.1039/c39950001013
• 作为产物：
  描述：

  在 四丁基氟化铵 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 6.5h， 生成 Ethyl 4-(benzenesulfinyl)-1-hydroxy-3-methylnaphthalene-2-carboxylate
  参考文献：
  名称：

  Novel ipso-Substitution of p-Sulfinylphenols through the Pummerer-Type Reaction:  A Selective and Efficient Synthesis of p-Quinones and Protected p-Dihydroquinones

  摘要：

  The treatment of p-sulfinylphenols 3a-q with trifluoroacetic anhydride caused a Pummerer-type reaction on aromatic rings and concomitant desulfurization to give mixtures of the corresponding p-dihydroquinones 9 and p-quinones 10, which were subsequently oxidized under mild conditions to provide high yields of p-quinones 10. On the other hand, the treatment of p-(phenylsulfinyl)-phenyl ethers 6 with trifluoroacetic anhydride in the presence of styrene caused the direct ipso-substitution of the sulfinyl groups into trifluoroacetoxy groups, giving the protected dihydroquinones 14 in high yields. Both types of reactions were generally completed below room temperature within 1 h and compatible with various functional groups such as the allyl, carbonyl, ester, amide, and silyloxy groups. The preparation of the p-sulfinylphenols 3 and the silyl ethers 6 is also described through p-specific thiocyanation of phenols followed by the Grignard reaction and oxidation.

  DOI：

  10.1021/jo970418o

文献信息

• An efficient synthesis of p-quinones utilizing a novel Pummerer-type rearrangement of p-sulfinylphenols
  作者：Shuji Akai、Yoshifumi Takeda、Kiyosei Iio、Yutaka Yoshida、Yasuyuki Kita

  DOI：10.1039/c39950001013

  日期：——

  Treatment of the p-sulfinylphenol derivatives 1 and 5 with trifluoroacetic anhydride causes a Pummerer-type rearrangement on aromatic rings and concomitant desulfurization to give 1 : 1 mixtures of the corresponding p-quinones and p-dihydroquinones, which are subjected to mild oxidation to provide high yields of p-quinones 3 and 7.

  对亚磺酰基苯酚衍生物 1 和 5 经三氟乙酸酐处理后，会在芳香环上发生普默尔型重排反应，同时发生脱硫反应，从而得到 1 : 1 的相应对醌和对二氢醌混合物。
• Isolation of the Quinone MonoO,S-Acetal Intermediates of the Aromatic Pummerer-Type Rearrangement ofp-Sulfinylphenols with 1-Ethoxyvinyl Esters
  作者：Yasuyuki Kita、Yoshifumi Tekeda、Masato Matsugi、Kiyosei Iio、Kentoku Gotanda、Kenji Murata、Shuji Akai

  DOI：10.1002/anie.199715291

  日期：1997.8.4
• Novel <i>ipso</i>-Substitution of <i>p</i>-Sulfinylphenols through the Pummerer-Type Reaction:  A Selective and Efficient Synthesis of <i>p</i>-Quinones and Protected <i>p</i>-Dihydroquinones
  作者：Shuji Akai、Yoshifumi Takeda、Kiyosei Iio、Kenji Takahashi、Nobuhisa Fukuda、Yasuyuki Kita

  DOI：10.1021/jo970418o

  日期：1997.8.1

  The treatment of p-sulfinylphenols 3a-q with trifluoroacetic anhydride caused a Pummerer-type reaction on aromatic rings and concomitant desulfurization to give mixtures of the corresponding p-dihydroquinones 9 and p-quinones 10, which were subsequently oxidized under mild conditions to provide high yields of p-quinones 10. On the other hand, the treatment of p-(phenylsulfinyl)-phenyl ethers 6 with trifluoroacetic anhydride in the presence of styrene caused the direct ipso-substitution of the sulfinyl groups into trifluoroacetoxy groups, giving the protected dihydroquinones 14 in high yields. Both types of reactions were generally completed below room temperature within 1 h and compatible with various functional groups such as the allyl, carbonyl, ester, amide, and silyloxy groups. The preparation of the p-sulfinylphenols 3 and the silyl ethers 6 is also described through p-specific thiocyanation of phenols followed by the Grignard reaction and oxidation.