1,1-dioxo-2,3-dimethylbenzothiophene | 16958-01-3

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1,1-dioxo-2,3-dimethylbenzothiophene
• 英文别名: 2,3-Dimethylbenzothiophene sulfone；2,3-dimethyl-benzo[b]thiophene-1,1-dioxide；2,3-Dimethyl-benzo[b]thiophen-1,1-dioxid；2,3-Dimethyl-benzothiophen-1,1-dioxid；2,3-Dimethyl-1H-1-benzothiophene-1,1-dione；2,3-dimethyl-1-benzothiophene 1,1-dioxide
• CAS: 16958-01-3
• 化学式: C₁₀H₁₀O₂S
• 分子量: 194.254
• InChiKey: VLHYBUMJZNACSI-UHFFFAOYSA-N

物化性质

• 沸点：
  369.0±25.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1-dioxo-2,3-dimethylbenzothiophene 以91%的产率得到
  参考文献：
  名称：

  KADYROV A. X.; HYMAHOB N. U.; NASYROV I. M., DOKL. AKAD. FANXOI. PCC TOCHIKISTON, DOKL. AN TADZHSSR, 1975, 18, HO 9, 3+

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二甲基苯并噻吩 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 0.25h， 生成 1,1-dioxo-2,3-dimethylbenzothiophene
  参考文献：
  名称：

  Transformations of six isomers of dimethylbenzothiophene by three Pseudomonas strains

  摘要：

  Dimethylbenzothiophenes are among the sulfur heterocycles in petroleum that are known to be degraded by microbial activity. Six of the 15 possible isomers of dimethylbenzothiophene were synthesized and used in biotransformation studies with three Pseudomonas isolates that oxidize a variety of condensed thiophenes including methylbenzothiophenes and methyldibenzothiophenes. The isomers of dimethylbenzothiophene were chosen to have a variety of substitution patterns: both methyl groups on the thiophene ring (the 2,3-isomer); a methyl group on each of the rings (the 2,7-, 3,5- and 3,7-isomers); and both methyl groups on the benzene ring (the 4,6- and 4,7-isomers). Each isolate was grown on l-methylnaphthalene or glucose in the presence of one of the dimethylbenzothiophenes and culture extracts were analyzed to identify nearly 30 sulfur-containing metabolites in total. Sulfoxides and sulfones were commonly found metabolites in culture extracts from the 2,3-, 2,7- and 3,7-isomers, whereas 2,3-diones, 3(2H)-ones and 2(3H)-ones were formed from the 4,6- and 4,7-isomers. High-molecular-weight products, some of which were tentatively identified as tetramethylbenzo[b]naphtho[1,2-d]thiophen were detected in the extracts of cultures incubated with 4,6- or 4,7-dimethylbenzothiophene. The methyl groups of all of the isomers, except 4,6-, were oxidized to give hydroxymethyl-methylbenzothiophenes and methylbenzothiophene-carboxylic acids, and these were the only products detected from the oxidation of 3,5-dimethylbenzothiophene.

  DOI：

  10.1007/bf00058180

文献信息

• Isoxazolidines by cycloadditions of N,α-diphenyl nitrone in the benzo[b]thiophene S-oxide and SS-dioxide series
  作者：Armand Bened、Robert Durand、Daniel Pioch、Patrick Geneste、Claude Guimon、Geneviève Pfister Guillouzo、Jean-Paul Declercq、Gabriel Germain、Pierrette Briard、Joelle Rambaud、Raymond Roques

  DOI：10.1039/p29840000001

  日期：——

  of N,α-diphenyl nitrone have been investigated in the 2- or 3-substituted (methyl, phenyl, chloro, bromo, piperidino, acetyl) benzo[b]thiophene S-oxide and SS-dioxide series. The S-oxide and SS-dioxide derivatives show the same ability to form adducts. The 2,3-dihydrobenzo[b]-thieno[2,3-d]isoxazolidines are generally formed only as a single regioisomer, except in the case of 2-methyl dipolarophiles

  已经研究了N，α-二苯基硝酮的1,3-偶极环加成反应是在2-或3-取代的（甲基，苯基，氯，溴，哌啶子基，乙酰基）苯并[ b ]噻吩S-氧化物和SS-二氧化物系列中进行的。 。该小号氧化物和SS二氧化物衍生物显示出，以形成加合物的能力相同。2,3-二氢苯并[ b ]-噻吩[2,3- d]异恶唑烷通常仅以单一的区域异构体形式形成，除了2-甲基双极性亲和剂形成两个区域异构体的情况以外。在CNDO / S计算和光电光谱电离势的基础上，根据边界轨道相互作用来讨论区域选择性。具有肘形形状的硝酮可能导致非对映异构体的形成，但实际上仅形成了反式-异恶唑烷。S-氧化物系列中的立体选择性较低，因为我们仅与3-甲基双极性亲和剂获得一种加合物，但与3-苯基衍生物同时获得了顺式和反式表位。溴衍生物不导致任何加合物。X给出了两种加合物的-射线结构，其对应于将硝基添加至苯并[ b ]噻吩SS-二氧化物和2-甲基衍生物。
• Werner, Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 509,515, 516
  作者：Werner

  DOI：——

  日期：——
• BENED, A.;DURAND, R.;PIOCH, D.;GENESTE, P.;GUIMON, C.;GUILLOUZO, G. P.;DE+, J. CHEM. SOC. PERKIN TRANS., 1984, N 1, 1-6
  作者：BENED, A.、DURAND, R.、PIOCH, D.、GENESTE, P.、GUIMON, C.、GUILLOUZO, G. P.、DE+

  DOI：——

  日期：——
• ROBUST PHOTOCHROMIC COMPOUNDS WITH SILICON- OR PHOSPHORUS-CONTAINING HETEROCYCLIC RING
  申请人：The University of Hong Kong

  公开号：EP3154990B1

  公开（公告）日：2019-09-11
• ROBUST PHOTOCHROMIC COMPOUNDS WITH SILICON- OR PHOSPHORUS-CONTAINING HETEROCYCLIC RING AND THE PRODUCTION THEREOF
  申请人：THE UNIVERSITY OF HONG KONG

  公开号：US20150361332A1

  公开（公告）日：2015-12-17

  In one embodiment, provided are a new class of diarylethene-containing photochromic compounds with the incorporation of silicon- or phosphorus-containing heterocycles into the “ethene” part of the diarylethene backbone that has been shown to be capable of displaying tunable, robust and thermally stable photochromic properties. Also provided are methods for synthesizing these compounds, as well as uses of these compounds as these compounds may be used as the photochromic layer in an optical recording material and other optical functioning devices.