Tert-butyl-dimethyl-(6-pyridin-2-ylselanylhexoxy)silane | 1224431-75-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Tert-butyl-dimethyl-(6-pyridin-2-ylselanylhexoxy)silane
• 英文别名: tert-butyl-dimethyl-(6-pyridin-2-ylselanylhexoxy)silane
• CAS: 1224431-75-7
• 化学式: C₁₇H₃₁NOSeSi
• 分子量: 372.485
• InChiKey: OQHYLDFJBPPJIL-UHFFFAOYSA-N

物化性质

• 沸点：
  397.5±38.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Tert-butyl-dimethyl-(6-pyridin-2-ylselanylhexoxy)silane 在 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 0.83h， 生成 PySeOH 、 叔丁基(5-己烯基氧基)二甲基硅烷
  参考文献：
  名称：

  Reaction of Dess–Martin periodinane with 2-(alkylselenyl)pyridines. Dehydration of primary alcohols under extraordinarily mild conditions

  摘要：

  Dess-Martin periodinane oxidizes very rapidly 2-pyridylseleno derivatives RR'CHCH2SePy in CHCl3 or CH2Cl2 and more chemoselectively than mCPBA. Tetravalent selenanes, RR'CHCH2Se(OAc)(2)Py, seem to be formed. Treatment of these intermediates with aqueous NaHCO3 gives rise to irreversible hydrolysis and elimination to terminal alkenes. As the OH/SePy exchange can be performed in minutes, the overall process is an exceptionally efficient procedure for the dehydration of primary alcohols. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.002
• 作为产物：
  描述：

  二(2-吡啶基)二硒醚 、 1-己醇,6-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]- 在 三甲基膦 作用下， 以 甲苯 为溶剂， 以100%的产率得到Tert-butyl-dimethyl-(6-pyridin-2-ylselanylhexoxy)silane
  参考文献：
  名称：

  Reaction of Dess–Martin periodinane with 2-(alkylselenyl)pyridines. Dehydration of primary alcohols under extraordinarily mild conditions

  摘要：

  Dess-Martin periodinane oxidizes very rapidly 2-pyridylseleno derivatives RR'CHCH2SePy in CHCl3 or CH2Cl2 and more chemoselectively than mCPBA. Tetravalent selenanes, RR'CHCH2Se(OAc)(2)Py, seem to be formed. Treatment of these intermediates with aqueous NaHCO3 gives rise to irreversible hydrolysis and elimination to terminal alkenes. As the OH/SePy exchange can be performed in minutes, the overall process is an exceptionally efficient procedure for the dehydration of primary alcohols. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.002

文献信息

• Reaction of Dess–Martin periodinane with 2-(alkylselenyl)pyridines. Dehydration of primary alcohols under extraordinarily mild conditions
  作者：Thanos Andreou、Jordi Burés、Jaume Vilarrasa

  DOI：10.1016/j.tetlet.2010.02.002

  日期：2010.4

  Dess-Martin periodinane oxidizes very rapidly 2-pyridylseleno derivatives RR'CHCH2SePy in CHCl3 or CH2Cl2 and more chemoselectively than mCPBA. Tetravalent selenanes, RR'CHCH2Se(OAc)(2)Py, seem to be formed. Treatment of these intermediates with aqueous NaHCO3 gives rise to irreversible hydrolysis and elimination to terminal alkenes. As the OH/SePy exchange can be performed in minutes, the overall process is an exceptionally efficient procedure for the dehydration of primary alcohols. (C) 2010 Elsevier Ltd. All rights reserved.