(Z)-dimethyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)-2-butendioate | 40886-49-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-dimethyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)-2-butendioate
• 英文别名: dimethyl 2-(1,1,3-trioxobenzo[d]isothiazol-2(3H)-yl)fumarate；(1,1,3-trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-fumaric acid dimethyl ester；Dimethylsaccharinofumarat；dimethyl (Z)-2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)but-2-enedioate
• CAS: 40886-49-5
• 化学式: C₁₃H₁₁NO₇S
• 分子量: 325.299
• InChiKey: SFOJYGPXPWFKPY-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z)-dimethyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)-2-butendioate 在 镍 氢气 作用下， 以 乙醇 为溶剂， 生成 (1,1,3-trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-succinic acid dimethyl ester
  参考文献：
  名称：

  Gudi,M.N.; George,M.V., Indian Journal of Chemistry, 1972, vol. 10, p. 881 - 887

  摘要：

  DOI：
• 作为产物：
  描述：

  糖精 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 0.05h， 生成 (Z)-dimethyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)-2-butendioate
  参考文献：
  名称：

  Microwave-Induced Stereoselective Conversion of Dialkyl 2-(1,1,3-Trioxo-1,3-dihydro-2 H -1,2-Benzisothiazol-2-yl)-3-(triphenylphosphoranylidene)succinates to Dialkyl 2-(1,1,3-Trioxo-1,3-dihydro-2 H -1,2-benzisothiazol-2-yl)-2-butendioates in the Presence of Silica-Gel Powder in Solvent-Free Conditions

  摘要：

  Protonation of the highly reactive 1: 1 intermediates produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates by saccharin leads to vinyltriphenylphosphonium salts, which undergo an addition reaction with a counter anion in CH2Cl2 at r.t. to produce the corresponding stabilized phosphorus ylides. Silica-gel powder was found to catalyze the stereoselective conversion of the stabilized phosphorus ylides to the corresponding electron-poor N-vinylated isothiazoles in solvent-free conditions under thermal and microwave irradiation in fairly good yields.

  DOI：

  10.1080/104265090969838

文献信息

• Pyridine-Mediated <i>N</i>-Vinylation of Heterocyclic Compounds: A Mild, Stereoselective and General Synthesis
  作者：Azam Shahraki、Alireza Hassanabadi

  DOI：10.3184/174751914x14112003835373

  日期：2014.10

  A good yield from the stereoselective synthesis of N-vinylated heterocyclic compounds is described involving the reaction of acetylenic esters and NH heterocyclic compounds in the presence of pyridine. This one-pot method is simple, effective under mild conditions and affords excellent yields.

  描述了 N-乙烯基化杂环化合物的立体选择性合成的良好收率，涉及炔酯和 NH 杂环化合物在吡啶存在下的反应。这种一锅法简单，在温和的条件下有效，并提供了极好的收率。
• Triphenylarsine as an Efficient Catalyst in Diastereospecific Synthesis of N-Vinyl Heterocyclic Compounds
  作者：Malek Taher Maghsoodlou、Reza Heydari、Sayyed Mostafa Habibi-Khorassani、Nourollah Hazeri、Mojtaba Lashkari、Mohsen Rostamizadeh、Seyed Sajad Sajadikhah

  DOI：10.1080/00397911003629432

  日期：2011.1.31

  [image omitted] A diastereospecific synthesis of N-vinyl heterocyclic compounds is described from a reaction of dialkyl acetylenedicarboxylate and N-H heterocyclic compounds, such as phthalimide, saccharin, 3(2H)-pyridazinone, isatin, maleimide, 2,4-thiazolidinedione, 2-benzoxazolinione and 6-chloro-2-benzoxazolinione, in the presence of triphenylarsine as an efficient catalyst, in excellent yield. The presented one-pot method is simple and effective with mild conditions.
• Gudi,M.N.; George,M.V., Indian Journal of Chemistry, 1972, vol. 10, p. 881 - 887
  作者：Gudi,M.N.、George,M.V.

  DOI：——

  日期：——
• Microwave-Induced Stereoselective Conversion of Dialkyl 2-(1,1,3-Trioxo-1,3-dihydro-2<b> <i>H</i> </b>-1,2-Benzisothiazol-2-yl)-3-(triphenylphosphoranylidene)succinates to Dialkyl 2-(1,1,3-Trioxo-1,3-dihydro-2<b> <i>H</i> </b>-1,2-benzisothiazol-2-yl)-2-butendioates in the Presence of Silica-Gel Powder in Solvent-Free Conditions
  作者：Ali Ramazani、Akram Abbasi Motejadded、Ebrahim Ahmadi

  DOI：10.1080/104265090969838

  日期：2006.1.1

  Protonation of the highly reactive 1: 1 intermediates produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates by saccharin leads to vinyltriphenylphosphonium salts, which undergo an addition reaction with a counter anion in CH2Cl2 at r.t. to produce the corresponding stabilized phosphorus ylides. Silica-gel powder was found to catalyze the stereoselective conversion of the stabilized phosphorus ylides to the corresponding electron-poor N-vinylated isothiazoles in solvent-free conditions under thermal and microwave irradiation in fairly good yields.