(R)-(-)-2,3-dihydro-3-phenyl-2-(toluene-4-sulfonyl)benzo[d]isothiazole

• 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: (R)-(-)-2,3-dihydro-3-phenyl-2-(toluene-4-sulfonyl)benzo[d]isothiazole
• 英文别名: (R)-2,3-dihydro-3-phenyl-2-(toluene-4-sulfonyl)benzo[d]isothiazole；(3R)-2-(4-methylphenyl)sulfonyl-3-phenyl-3H-1,2-benzothiazole
• 化学式: C₂₀H₁₇NO₂S₂
• 分子量: 367.492
• InChiKey: XKMODKOUKFLQHZ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	[1R,(S)S]-(-)-N-{[2-(tert-butylsulfinyl)phenyl]phenylmethyl}-4-methylbenzenesulfonamide	885130-27-8	C24H27NO3S2	441.615

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(R)-4,5-dihydro-2-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyl)-5-phenyl-1,4-benzo[f]thiazepine	1349198-44-2	C29H25NO4S3	547.72
  ——	methyl (5R)-4-(4-methylphenyl)sulfonyl-5-phenyl-5H-1,4-benzothiazepine-2-carboxylate	1349198-41-9	C24H21NO4S2	451.567

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2,3-dihydro-3-phenyl-2-(toluene-4-sulfonyl)benzo[d]isothiazole 在 对甲苯磺酸 、 二乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 27.08h， 生成 (R)-4,5-dihydro-2-methyl-4-(toluene-4-sulfonyl)-5-phenyl-1,4-benzo[f]thiazepine
  参考文献：
  名称：

  环亚磺酰胺：用于合成1,4-苯并硫氮杂s的通用模板

  摘要：

  通过假定的烯丙酸酯中间体，通过环亚磺酰胺与丙炔酸甲酯或吡啶催化的甲苯磺酰基乙炔的环扩环反应，已经实现了在位置2和5上取代的1,4-苯并硫氮杂卓的两种有效合成。或通过由二乙胺促进的α-亚磺酰基化反应和随后的酸催化的缩合反应。

  DOI：

  10.1016/j.tetlet.2011.07.148
• 作为产物：
  描述：

  [1R,(S)S]-(-)-N-{[2-(tert-butylsulfinyl)phenyl]phenylmethyl}-4-methylbenzenesulfonamide 以 甲苯 为溶剂， 反应 0.33h， 以93%的产率得到(R)-(-)-2,3-dihydro-3-phenyl-2-(toluene-4-sulfonyl)benzo[d]isothiazole
  参考文献：
  名称：

  ortho-Metalation of Enantiopure Aromatic Sulfoxides and Stereocontrolled Addition to Imines

  摘要：

  Enantiopure aromatic (phenyl, naphthyl) and heteroaromatic (pyridyl, quinolyl, diazinyl) sulfoxides have been synthesized by reaction of (S)-tert-butyl tert-butanethiosulfinate with aryl- or heteroaryllithium derivatives. The ortho-directed metalation of the sulfoxides was performed with lithium bases. Subsequent addition of the lithiated intermediates to N-tosylimines afforded tosylaminoalkyl tert-butylsulfinyl arenes. In most cases a complete asymmetric induction was highlighted in favor of (S,S) isomers. Heating the aminosulfoxides provided an original cyclization to form novel cyclic sulfenamides. A novel enantiopure synthesis of a benzylamine was described. An application of an enantiopure aminosulfoxide as N,S ligand for the asymmetric catalysis of allylic nucleophilic substitution has been successfully tested.

  DOI：

  10.1021/jo052358p

文献信息

• Fluoride Ion and Phosphines as Nucleophilic Catalysts: Synthesis of 1,4-Benzothiazepines from Cyclic Sulfenamides
  作者：Cédric Spitz、Jean-François Lohier、Jana Sopkova-de Oliveira Santos、Vincent Reboul、Patrick Metzner

  DOI：10.1021/jo900449a

  日期：2009.5.15

  A new methodology, using fluoride ion as a nucleophilic catalyst, was applied for the synthesis of enantiopure 1,4-benzothiazepine from cyclic sulfenamide and electron-deficient acetylene, with high efficiency and atom economy.

  以氟离子为亲核催化剂的一种新方法，被用于由环亚磺酰胺和电子缺陷型乙炔合成对映体纯的1，4-苯并噻嗪类，具有较高的效率和原子经济性。
• Catalytic Generation of Cesium Acetylide by CsF: Synthesis of 1,3-Benzothiazines from Cyclic Sulfenamides
  作者：Cédric Spitz、Jean-François Lohier、Vincent Reboul、Patrick Metzner

  DOI：10.1021/ol9009333

  日期：2009.7.2

  An efficient synthesis of enantiopure 1,3-benzothiazines has been achieved by reaction of cyclic sulfenamides and alkylpropiolate or tosylacetylene catalyzed by cesium fluoride.
• <i>ortho</i>-Metalation of Enantiopure Aromatic Sulfoxides and Stereocontrolled Addition to Imines
  作者：Nicolas Le Fur、Ljubica Mojovic、Nelly Plé、Alain Turck、Vincent Reboul、Patrick Metzner

  DOI：10.1021/jo052358p

  日期：2006.3.31

  Enantiopure aromatic (phenyl, naphthyl) and heteroaromatic (pyridyl, quinolyl, diazinyl) sulfoxides have been synthesized by reaction of (S)-tert-butyl tert-butanethiosulfinate with aryl- or heteroaryllithium derivatives. The ortho-directed metalation of the sulfoxides was performed with lithium bases. Subsequent addition of the lithiated intermediates to N-tosylimines afforded tosylaminoalkyl tert-butylsulfinyl arenes. In most cases a complete asymmetric induction was highlighted in favor of (S,S) isomers. Heating the aminosulfoxides provided an original cyclization to form novel cyclic sulfenamides. A novel enantiopure synthesis of a benzylamine was described. An application of an enantiopure aminosulfoxide as N,S ligand for the asymmetric catalysis of allylic nucleophilic substitution has been successfully tested.
• Cyclic sulfenamide: versatile template for the synthesis of 1,4-benzothiazepines
  作者：Cédric Spitz、Vincent Reboul、Patrick Metzner

  DOI：10.1016/j.tetlet.2011.07.148

  日期：2011.11

  Two efficient syntheses of 1,4-benzothiazepines, substituted in the positions 2 and 5, have been achieved either by a ring expansion reaction of cyclic sulfenamides with methylpropiolate or tosylacetylene catalyzed by pyridine, via a postulated allenolate intermediate; or by an α-sulfenylation reaction promoted by diethylamine and a subsequent acid catalyzed condensation reaction.

  通过假定的烯丙酸酯中间体，通过环亚磺酰胺与丙炔酸甲酯或吡啶催化的甲苯磺酰基乙炔的环扩环反应，已经实现了在位置2和5上取代的1,4-苯并硫氮杂卓的两种有效合成。或通过由二乙胺促进的α-亚磺酰基化反应和随后的酸催化的缩合反应。