diethyl 1,4-dioxo-1,4-dihydronaphthalene-2,3-dicarboxylate | 15207-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: diethyl 1,4-dioxo-1,4-dihydronaphthalene-2,3-dicarboxylate
• 英文别名: 1,4-Dioxo-1,4-dihydro-naphthalin-1,2-dicarbonsaeure-diethylester；Diethyl 1,4-dioxonaphthalene-2,3-dicarboxylate
• CAS: 15207-22-4
• 化学式: C₁₆H₁₄O₆
• 分子量: 302.284
• InChiKey: FSKKSWPVIAMNPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  53.7-54.7 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  436.0±45.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 1,4-dioxo-1,4-dihydronaphthalene-2,3-dicarboxylate 在 溶剂黄146 作用下， 生成 5-hydroxy-1-benzyl-2-methyl-1H-benzo[g]indole-3,4-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Nenitzescu反应中的2,3-二羧酸二烷基醌

  摘要：

  萘醌-2,3-二羧酸二乙酯与不同的烯胺反应，通过一个乙氧基羰基的迁移生成5-oxo-1,5-二氢-苯并[ g ]吲哚-3,4,9b-三羧酸酯衍生物。这些新产品通过消除一个乙氧羰基将其芳香化为平面吲哚。通过N，N-二甲基-烯胺环化，通过乙氧基羰基的迁移产生5-氧代-4,5-二氢-环戊[ a ]萘-3,3a，4-三羧酸酯以及萘基-丙二酸衍生物。

  DOI：

  10.1016/j.tet.2005.07.032
• 作为产物：
  描述：

  Diethyl 1-(benzenesulfinyl)-4-hydroxynaphthalene-2,3-dicarboxylate 在 manganese(IV) oxide 、 三氟乙酸酐 作用下， 生成 diethyl 1,4-dioxo-1,4-dihydronaphthalene-2,3-dicarboxylate
  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

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。
• Sharma,S.C.; Torssell,K., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1978, vol. 32, p. 347 - 353
  作者：Sharma,S.C.、Torssell,K.

  DOI：——

  日期：——
• SHARMA S. C.; TORSSELL K., ACTA CHEM. SCAND., 1978, B 32, NO 5, 347-353
  作者：SHARMA S. C.、 TORSSELL K.

  DOI：——

  日期：——
• 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.
• Dialkyl quinone-2,3-dicarboxylates in the Nenitzescu reaction
  作者：L.W. Schenck、A. Sippel、K. Kuna、W. Frank、A. Albert、U. Kucklaender

  DOI：10.1016/j.tet.2005.07.032

  日期：2005.9

  Diethyl naphthoquinone-2,3-dicarboxylate reacts with different enamines to give 5-oxo-1,5-dihydro-benzo[g]indole-3,4,9b-tricarboxylate derivatives by migration of one ethoxycarbonyl group. These new products aromatize to planar indoles by elimination of one ethoxycarbonylgroup. With an N,N-dimethyl-enamine cyclization yields a 5-oxo-4,5-dihydro-cyclopenta[a]naphthalene-3,3a,4-tricarboxylate as well

  萘醌-2,3-二羧酸二乙酯与不同的烯胺反应，通过一个乙氧基羰基的迁移生成5-oxo-1,5-二氢-苯并[ g ]吲哚-3,4,9b-三羧酸酯衍生物。这些新产品通过消除一个乙氧羰基将其芳香化为平面吲哚。通过N，N-二甲基-烯胺环化，通过乙氧基羰基的迁移产生5-氧代-4,5-二氢-环戊[ a ]萘-3,3a，4-三羧酸酯以及萘基-丙二酸衍生物。