tert-Butyl-dimethyl-(3,3,4,6,7-pentamethyl-2,3-dihydro-benzo[b]thiophen-5-yloxy)-silane | 205182-92-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: tert-Butyl-dimethyl-(3,3,4,6,7-pentamethyl-2,3-dihydro-benzo[b]thiophen-5-yloxy)-silane
• 英文别名: tert-butyl-dimethyl-[(3,3,4,6,7-pentamethyl-2H-1-benzothiophen-5-yl)oxy]silane
• CAS: 205182-92-9
• 化学式: C₁₉H₃₂OSSi
• 分子量: 336.614
• InChiKey: XFPUKPJEBRFWPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.38
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-Butyl-dimethyl-(3,3,4,6,7-pentamethyl-2,3-dihydro-benzo[b]thiophen-5-yloxy)-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以79%的产率得到3,3,4,6,7-pentamethyl-2,3-dihydrobenzo[b]thiophene-5-ol
  参考文献：
  名称：

  Novel Antioxidants:  Unexpected Rearrangements in the Radical Cyclization Approach to 2,3-Dihydrobenzo[b]thiophene-5-ol Derivatives

  摘要：

  The novel alpha-tocopherol analogue 3,3,4,6,7-pentamethyl-2,3-dihydrobenzo[b]thiophene-5-ol (4a) was prepared by cyclodehydration of the aryl 2-hydroxyalkyl sulfide 6 in concentrated sulfuric acid. Aromatic bromination and dehydration of alcohol 6 furnished the 2-bromoaryl methallyl sulfide 10a as the kinetic product and the 2-bromoaryl 2-methyl-2-propenyl sulfide 11a as the thermodynamic one. Radical cyclization of these compounds afforded the desired 2,3-dihydrobenzo[b]thiophene derivative 12 in addition to a rearranged isomer 13 thereof. It is proposed that the transformation of compound 10a to 13 occurs via 6-endo cyclization, beta-scission, and subsequent 5-exo cyclization. The radical cyclization of the 2-bromoaryl allyl sulfide 16, unsubstituted in the allylic moiety, furnished only 2,3-dihydrobenzo[b]thiophene-5-ol derivative 17.

  DOI：

  10.1021/jo972087l
• 作为产物：
  描述：

  [3-Bromo-4-(2-bromo-2-methyl-propylsulfanyl)-2,5,6-trimethyl-phenoxy]-tert-butyl-dimethyl-silane 在 偶氮二异丁腈 、 三正丁基氢锡 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 甲苯 、 苯 为溶剂， 反应 7.0h， 生成 tert-Butyl-dimethyl-(3,3,4,6,7-pentamethyl-2,3-dihydro-benzo[b]thiophen-5-yloxy)-silane
  参考文献：
  名称：

  Novel Antioxidants:  Unexpected Rearrangements in the Radical Cyclization Approach to 2,3-Dihydrobenzo[b]thiophene-5-ol Derivatives

  摘要：

  The novel alpha-tocopherol analogue 3,3,4,6,7-pentamethyl-2,3-dihydrobenzo[b]thiophene-5-ol (4a) was prepared by cyclodehydration of the aryl 2-hydroxyalkyl sulfide 6 in concentrated sulfuric acid. Aromatic bromination and dehydration of alcohol 6 furnished the 2-bromoaryl methallyl sulfide 10a as the kinetic product and the 2-bromoaryl 2-methyl-2-propenyl sulfide 11a as the thermodynamic one. Radical cyclization of these compounds afforded the desired 2,3-dihydrobenzo[b]thiophene derivative 12 in addition to a rearranged isomer 13 thereof. It is proposed that the transformation of compound 10a to 13 occurs via 6-endo cyclization, beta-scission, and subsequent 5-exo cyclization. The radical cyclization of the 2-bromoaryl allyl sulfide 16, unsubstituted in the allylic moiety, furnished only 2,3-dihydrobenzo[b]thiophene-5-ol derivative 17.

  DOI：

  10.1021/jo972087l

文献信息

• Novel Antioxidants:  Unexpected Rearrangements in the Radical Cyclization Approach to 2,3-Dihydrobenzo[<i>b</i>]thiophene-5-ol Derivatives
  作者：Jonas Malmström、Vijay Gupta、Lars Engman

  DOI：10.1021/jo972087l

  日期：1998.5.1

  The novel alpha-tocopherol analogue 3,3,4,6,7-pentamethyl-2,3-dihydrobenzo[b]thiophene-5-ol (4a) was prepared by cyclodehydration of the aryl 2-hydroxyalkyl sulfide 6 in concentrated sulfuric acid. Aromatic bromination and dehydration of alcohol 6 furnished the 2-bromoaryl methallyl sulfide 10a as the kinetic product and the 2-bromoaryl 2-methyl-2-propenyl sulfide 11a as the thermodynamic one. Radical cyclization of these compounds afforded the desired 2,3-dihydrobenzo[b]thiophene derivative 12 in addition to a rearranged isomer 13 thereof. It is proposed that the transformation of compound 10a to 13 occurs via 6-endo cyclization, beta-scission, and subsequent 5-exo cyclization. The radical cyclization of the 2-bromoaryl allyl sulfide 16, unsubstituted in the allylic moiety, furnished only 2,3-dihydrobenzo[b]thiophene-5-ol derivative 17.