2-(tert-Butyl-dimethyl-silanyl)-4,5-dimethyl-3,6-dihydro-2H-[1,2]thiazine 1-oxide | 131196-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-(tert-Butyl-dimethyl-silanyl)-4,5-dimethyl-3,6-dihydro-2H-[1,2]thiazine 1-oxide
• CAS: 131196-15-1
• 化学式: C₁₂H₂₅NOSSi
• 分子量: 259.488
• InChiKey: CSROMBKKPLCEEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(tert-Butyl-dimethyl-silanyl)-4,5-dimethyl-3,6-dihydro-2H-[1,2]thiazine 1-oxide 在 甲基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以86%的产率得到
  参考文献：
  名称：

  Metalation and alkylation of 3,6-dihydrothiazine 1-oxides prepared via Diels-Alder cycloadditions of N-sulfinyl dienophiles

  摘要：

  The deprotonation of various 3,6-dihydrothiazine 1-oxides using LDA or methyllithium has been investigated. It was found that the stability and chemistry of these lithiated heterocycles are highly dependent upon the nature of the ring nitrogen substituent. Thus, N-alkyldihydrothiazine oxides can be metalated at C-6 to give species postulated as 9, which undergo predominantly anti alkylation with alkyl halides. Alternatively, with MeOD, 9 is deuterated at C-6 primarily in a syn mode. N-Silylated heterocycles ring open rapidly and stereoselectively upon metalation to give dienic sulfinamides like 19, which can be reclosed to the starting dihydrothiazine oxides. N-Phenyl-substituted 3,6-dihydrothiazine 1-oxides upon metalation give mixtures of pyrroles and N-S bond cleavage products. Attempts to generate the dianion from NH dihydrothiazine oxide 17 led only to low yields of C-4 alkylated products with alkyl halides.

  DOI：

  10.1021/jo00001a068
• 作为产物：
  描述：

  在 sodium hydride 作用下， 以 四氢呋喃 、 paraffin 为溶剂， 反应 3.0h， 以70%的产率得到2-(tert-Butyl-dimethyl-silanyl)-4,5-dimethyl-3,6-dihydro-2H-[1,2]thiazine 1-oxide
  参考文献：
  名称：

  Metalation and alkylation of 3,6-dihydrothiazine 1-oxides prepared via Diels-Alder cycloadditions of N-sulfinyl dienophiles

  摘要：

  The deprotonation of various 3,6-dihydrothiazine 1-oxides using LDA or methyllithium has been investigated. It was found that the stability and chemistry of these lithiated heterocycles are highly dependent upon the nature of the ring nitrogen substituent. Thus, N-alkyldihydrothiazine oxides can be metalated at C-6 to give species postulated as 9, which undergo predominantly anti alkylation with alkyl halides. Alternatively, with MeOD, 9 is deuterated at C-6 primarily in a syn mode. N-Silylated heterocycles ring open rapidly and stereoselectively upon metalation to give dienic sulfinamides like 19, which can be reclosed to the starting dihydrothiazine oxides. N-Phenyl-substituted 3,6-dihydrothiazine 1-oxides upon metalation give mixtures of pyrroles and N-S bond cleavage products. Attempts to generate the dianion from NH dihydrothiazine oxide 17 led only to low yields of C-4 alkylated products with alkyl halides.

  DOI：

  10.1021/jo00001a068