(R)-2-(trimethylsilyl)ethyl 1-hydroxy-4-(4-nitrophenoxy)-butan-2-ylcarbamate | 872864-63-6

• 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-(trimethylsilyl)ethyl 1-hydroxy-4-(4-nitrophenoxy)-butan-2-ylcarbamate
• 英文别名: 2-trimethylsilylethyl N-[(2R)-1-hydroxy-4-(4-nitrophenoxy)butan-2-yl]carbamate
• CAS: 872864-63-6
• 化学式: C₁₆H₂₆N₂O₆Si
• 分子量: 370.478
• InChiKey: AROFPZAXVKFRNT-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-2-(trimethylsilyl)ethyl 1-hydroxy-4-(4-nitrophenoxy)-butan-2-ylcarbamate 在 1% Pd/C 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  The asymmetric aminohydroxylation route to GABOB and homoserine derivatives

  摘要：

  The 4-nitrophenyl ether is an efficient directing group in the asymmetric aminohydroxylation reaction of homoallylic ether derivatives. Either regioisomeric product can be obtained with useful levels of enantioselectivity allowing for the short enantioselective synthesis of GABOB and homoserine derivatives. A model based on substrate-catalyst interactions is presented to explain the regio- and enantioselectivity of the aminohydroxylation reactions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.037
• 作为产物：
  描述：

  2-三甲基甲硅烷基乙基氨基甲酸酯 、 1-(but-3-en-1-yloxy)-4-nitrobenzene 在 potassium osmate(VI) dihydrate 、 sodium hydroxide 、 1,3-二氯-5,5-二甲基海因 、 水 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 丙醇 为溶剂， 反应 18.0h， 以65%的产率得到(R)-2-(trimethylsilyl)ethyl 1-hydroxy-4-(4-nitrophenoxy)-butan-2-ylcarbamate
  参考文献：
  名称：

  The asymmetric aminohydroxylation route to GABOB and homoserine derivatives

  摘要：

  The 4-nitrophenyl ether is an efficient directing group in the asymmetric aminohydroxylation reaction of homoallylic ether derivatives. Either regioisomeric product can be obtained with useful levels of enantioselectivity allowing for the short enantioselective synthesis of GABOB and homoserine derivatives. A model based on substrate-catalyst interactions is presented to explain the regio- and enantioselectivity of the aminohydroxylation reactions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.037

文献信息

• Substrate Control in the Asymmetric Aminohydroxylation of ­Monosubstituted Alkenes: The Enantioselective Synthesis of GABOB and ­Homoserine Derivatives
  作者：Malcolm D. McLeod、Michael Harding、Jennifer A. Bodkin、Craig A. Hutton

  DOI：10.1055/s-2005-918939

  日期：——

  group in the asymmetric aminohydroxylation reaction of but-3-en-1-ol derivatives. Either regioisomeric product can he obtained with useful levels of eoantioselectivity, allowing for the short enantioselective synthesis of GABOB and homoserine derivatives.

  4-硝基苯基醚是but-3-en-1-ol衍生物的不对称氨基羟基化反应中的有效导向基团。可以获得具有有用水平的对映选择性的任一区域异构产物，允许GABOB和高丝氨酸衍生物的短对映选择性合成。