dimethyl 2-(1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one-2-yl)-3-(triphenylphosphanylidene)-succinate | 519187-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 2-(1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one-2-yl)-3-(triphenylphosphanylidene)-succinate
• 英文别名: dimethyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)-3-(triphenylphosphoranylidene)succinate；dimethyl 2-(1,1,3-trioxo-2,3-dihydrobenzo[d]isothiazol-2-yl)-3-(triphenylphosphanylidene)butanedioate；Dimethyl 2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)-3-(triphenyl-lambda5-phosphanylidene)butanedioate；dimethyl 2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)-3-(triphenyl-λ5-phosphanylidene)butanedioate
• CAS: 519187-06-5
• 化学式: C₃₁H₂₆NO₇PS
• 分子量: 587.59
• InChiKey: RRRDMGKBAPFTPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  dimethyl 2-(1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one-2-yl)-3-(triphenylphosphanylidene)-succinate 以 甲苯 为溶剂， 反应 24.0h， 生成 (E)-dimethyl 2-(1,1-dioxo-1H-1λ⁶-benzo[d]isothiazol-3-yl)-but-2-enedioate 、 (Z)-dimethyl 2-(1,1-dioxo-1H-1λ⁶-benzo[d]isothiazol-3-yl)-but-2-enedioate
  参考文献：
  名称：

  Triphenylphosphine-Catalyzed Simple Synthesis of Vinyl-Substituted Saccharins

  摘要：

  Saccharin (1,1-dioxo-1,2-dihydro-1lambda(6)-benzo[d]-isothiazol-3-one) undergoes a smooth reaction with dialkyl acetylenedicarboxylates in the presence of triphenylphosphine to produce highly-functionalized salt-free sulfur-containing ylides in nearly quantitative yields. These stabilized phosphorus ylides exist as a mixture of two geometrical isomers as a result of restricted rotation around the carbon-carbon partial double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group. These ylides are converted to dialkyl 2-(1,1-dioxo-1H-1lambda(6)-benzo[d]-isothiazol-3-yl)-but-2-enedioates in boiling toluene.

  DOI：

  10.1080/10426500214574
• 作为产物：
  描述：

  丁炔二酸二甲酯 、 三苯基膦 、 糖精 以 乙酸乙酯 为溶剂， 反应 4.0h， 以95%的产率得到dimethyl 2-(1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one-2-yl)-3-(triphenylphosphanylidene)-succinate
  参考文献：
  名称：

  Triphenylphosphine-Catalyzed Simple Synthesis of Vinyl-Substituted Saccharins

  摘要：

  Saccharin (1,1-dioxo-1,2-dihydro-1lambda(6)-benzo[d]-isothiazol-3-one) undergoes a smooth reaction with dialkyl acetylenedicarboxylates in the presence of triphenylphosphine to produce highly-functionalized salt-free sulfur-containing ylides in nearly quantitative yields. These stabilized phosphorus ylides exist as a mixture of two geometrical isomers as a result of restricted rotation around the carbon-carbon partial double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group. These ylides are converted to dialkyl 2-(1,1-dioxo-1H-1lambda(6)-benzo[d]-isothiazol-3-yl)-but-2-enedioates in boiling toluene.

  DOI：

  10.1080/10426500214574

文献信息

• Hazeri, Nourollah; Khorassani, Sayyed M. H.; Maghsoodlou, Malek T., Journal of Chemical Research, 2006, # 4, p. 215 - 217
  作者：Hazeri, Nourollah、Khorassani, Sayyed M. H.、Maghsoodlou, Malek T.、Marandi, Ghasem、Nassiri, Mahmoud、Shahzadeh, Aqil G.

  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.