4,7-dimethoxy-1,3-dihydrobenzo[c]thiophene 2,2-dioxide | 19164-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,7-dimethoxy-1,3-dihydrobenzo[c]thiophene 2,2-dioxide
• 英文别名: 4,7-dimethoxy-1,3-dihydro-2-benzothiophene 2,2-dioxide
• CAS: 19164-86-4
• 化学式: C₁₀H₁₂O₄S
• 分子量: 228.269
• InChiKey: XXFNOVVCAMXCKI-UHFFFAOYSA-N

物化性质

• 沸点：
  496.7±45.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,7-dimethoxy-1,3-dihydrobenzo[c]thiophene 2,2-dioxide 以48%的产率得到2,5-dimethoxybicyclo<4.2.0>octa-1,3,5-triene
  参考文献：
  名称：

  Total synthesis of (+)-halenaquinol and (+)-halenaquinone. Experimental proof of their absolute stereostructures theoretically determined

  摘要：

  DOI：

  10.1021/ja00233a026
• 作为产物：
  描述：

  2-(Iodomethyl)-3,6-dimethoxybenzaldehyde 在 盐酸 、 sodium tetrahydroborate 、 二氧化硫 、 sodium iodide 、 锌 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 4,7-dimethoxy-1,3-dihydrobenzo[c]thiophene 2,2-dioxide
  参考文献：
  名称：

  Efficient synthesis of 5,8-disubstituted-1,4-dihydrobenzoxathiin-3-oxides and their isomeric structures, 4,7-disubstituted-1,3-dihydrobenzo[b] thiophene-2,2-dioxides

  摘要：

  Functionalized dihydrobenzoxathiin oxides and dihydrobenzothiophene-2,2-dioxides 11-18 have been prepared via trapping of sulfur dioxide under photolytic or ground state conditions.

  DOI：

  10.1016/s0040-4039(00)76956-5

文献信息

• A New Synthesis of Benzo[<i>b</i>]acridones
  作者：Artur Silva、Raquel Seixas、Diana Pinto、José Cavaleiro

  DOI：10.1055/s-0028-1087372

  日期：——

  A novel and efficient route for the synthesis of new benzo[b]acridones has been described. It involves the Diels-Alder reaction of N-substituted-4-quinolone-3-carbaldehyde with ortho-benzoquinodimethanes giving benzo[b]-1,6,6a,12a-tetrahydroacridones, which are the result of a cycloaddition reaction followed by an in situ deformylation. The oxidation of these tetrahydroacridones in dimethyl sulfoxide using a catalytic amount of iodine gives the new benzo[b]acridone derivatives. It was demonstrated that the ­cycloaddition reaction is only efficient if an electron-withdrawing N-protecting group is present.

  本研究描述了合成新苯并[b]吖啶酮的新颖而高效的路线。该方法涉及 N-取代-4-喹啉酮-3-甲醛与邻苯醌二甲烷的 Diels-Alder 反应，通过环加成反应和原位变形反应生成苯并[b]-1,6,6a,12a-四氢吖啶酮。使用一定量的碘催化这些四氢吖啶酮在二甲基亚砜中的氧化反应，可以得到新的苯并[b]吖啶酮衍生物。实验证明，只有当存在一个电子撤回的 N 保护基团时，环化反应才会有效。
• New Benzo[ b ]xanthones from Diels-Alder Reactions of Chromone-3-carboxaldehydes with ortho -Benzoquinodimethanes
  作者：Angela Sandulache、Artur M. S. Silva、Jos� A. S. Cavaleiro

  DOI：10.1007/s00706-002-0567-7

  日期：2003.3.1

  New benzo[b]xanthone derivatives, having substituents in the A and D rings, were prepared from cycloaddition reactions of chromone-3-carboxaldehydes with ortho-benzoquinodimethanes, generated in situ from 1,3-dihydrobenzo[c]thiophene 2,2-dioxide, followed by oxidation of the obtained diastereomeric adducts. The structure of all compounds was fully established by 1D and 2D NMR, MS, and elemental analysis. The stereochemistry of the obtained diastereomeric cycloadducts was established by NOESY experiments.
• A green and sustainable method for the oxidation of 1,3-dihydrobenzo[c]thiophenes to sulfones using metalloporphyrin complexes
  作者：Gustavo da Silva、Sónia M.G. Pires、Vera L.M. Silva、Mário M.Q. Simões、M. Graça P.M.S. Neves、Susana L.H. Rebelo、Artur M.S. Silva、José A.S. Cavaleiro

  DOI：10.1016/j.catcom.2014.06.032

  日期：2014.11

  Two efficient methods are reported for the oxidation of 1,3-dihydrobenzo[c]thiophenes to sulfones in good to high yields using H2O2 in the presence of catalytic amounts of porphyrin-based catalysts in ethanol or acetonitrile as solvents at room temperature. The presence of electron-donating or electron-withdrawing groups, in the benzene ring of 1,3-dihydrobenzo[c]thiophene, is well tolerated. (C) 2014 Elsevier B.V. All rights reserved.
• Protein tyrosine kinase inhibitory properties of planar polycyclics obtained from the marine sponge Xestospongia cf. carbonaria and from total synthesis
  作者：Khisal A. Alvi、Jaime Rodriguez、Maria Cristina Diaz、Robert Moretti、Robert S. Wilhelm、Rita H. Lee、Doris L. Slate、Phillip Crews

  DOI：10.1021/jo00070a023

  日期：1993.8

  Nine related polycyclic quinones and hydroquinones of the halenaquinone class were isolated from two Indo-Pacific collections of the sponge Xestospongia cf. carbonaria. The halenaquinone family appears not to be of polyketide origin but can be biogenetically derived by the union of a sesquiterpene and a quinone. Four new metabolites were characterized including tetrahydrohalenaquinone B (8a), 14-methoxyhalenaquinone (9), xestoquinolide A (10), and xestoquinolide B (11). These were accompanied by five known compounds, halenaquinone (3), halenaquinol (4), halenaquinol sulfate (5), xestoquinone (6), and tetrahydrohalenaquinone A (7a). The new structures were established from 2D NMR data, and the absolute stereochemistry of the chiral centers in 7 and 8 was determined by the formation of 7b and 7c, the bis esters of O-methylmandelic acid. A series of polycyclic models of natural products 3 and 6 were synthesized and included 16-23. The more complex members of this group were assembled via a 4 + 2 cycloaddition between an o-quinodimethane and a functionalized enone. The marine natural products plus two known fungal metabolites, viridin (13) and wortmannin (14), along with halenaquinone synthetic model compounds, were each tested for their ability to inhibit the activity of pp60v-src protein tyrosine kinase (PTK). Halenaquinone and 14-methoxyhalenaquinone were the most potent with IC50 values <10 muM. The other compounds were either less potent or inactive, and a rationalization for this SAR (structure activity relationship) pattern is presented.
• HARADA, NOBUYUKI;SUGIOKA, TATSUO;ANDO, YESUKE;UDA, HISASHI;KURIK, TAKEO, J. AMER. CHEM. SOC., 110,(1988) N 25, C. 8483-8487
  作者：HARADA, NOBUYUKI、SUGIOKA, TATSUO、ANDO, YESUKE、UDA, HISASHI、KURIK, TAKEO

  DOI：——

  日期：——