(1R)-2,2,2-trifluoro-1-(tert-butyldimethylsilyloxymethyl)ethyl-1-(N-benzyloxycarbonyl)amine | 959610-14-1

• 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: (1R)-2,2,2-trifluoro-1-(tert-butyldimethylsilyloxymethyl)ethyl-1-(N-benzyloxycarbonyl)amine
• 英文别名: benzyl N-[(2R)-3-[tert-butyl(dimethyl)silyl]oxy-1,1,1-trifluoropropan-2-yl]carbamate
• CAS: 959610-14-1
• 化学式: C₁₇H₂₆F₃NO₃Si
• 分子量: 377.479
• InChiKey: BAINPZRZCILALB-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R)-2,2,2-trifluoro-1-(tert-butyldimethylsilyloxymethyl)ethyl-1-(N-benzyloxycarbonyl)amine 、 5-溴-1-戊烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到(1R)-2,2,2-trifluoro-1-(tert-butyldimethylsilyloxymethyl)ethyl-1-(N-benzyloxycarbonyl-N-4-pentyl)amine
  参考文献：
  名称：

  Asymmetric Synthesis of Fluorinated Amino Macrolactones through Ring-Closing Metathesis

  摘要：

  The synthesis of new chiral fluorinated amino and azamacrolactones of types 1 and 2 is described. A ring-closing metathesis (RCM) reaction constitutes the key step in this methodology, which uses fluorinated amino alcohols 7 as starting materials. The influence of the CF2 group, which is located in the (x-position relative to the carbon bearing the amino group, on the efficiency of the RCM reaction is noteworthy. This method allows for the preparation of the desired fluorinated macrolactones in excellent yields.

  DOI：

  10.1021/jo701484w
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 (-)-(2R)-2-(N-benzyloxycarbonyl)amino-3,3,3-trifluoropropanol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到(1R)-2,2,2-trifluoro-1-(tert-butyldimethylsilyloxymethyl)ethyl-1-(N-benzyloxycarbonyl)amine
  参考文献：
  名称：

  Asymmetric Synthesis of Fluorinated Amino Macrolactones through Ring-Closing Metathesis

  摘要：

  The synthesis of new chiral fluorinated amino and azamacrolactones of types 1 and 2 is described. A ring-closing metathesis (RCM) reaction constitutes the key step in this methodology, which uses fluorinated amino alcohols 7 as starting materials. The influence of the CF2 group, which is located in the (x-position relative to the carbon bearing the amino group, on the efficiency of the RCM reaction is noteworthy. This method allows for the preparation of the desired fluorinated macrolactones in excellent yields.

  DOI：

  10.1021/jo701484w

文献信息

• Asymmetric Synthesis of Fluorinated Amino Macrolactones through Ring-Closing Metathesis
  作者：Santos Fustero、Begoña Fernández、Juan F. Sanz-Cervera、Natalia Mateu、Silvia Mosulén、Rodrigo J. Carbajo、Antonio Pineda-Lucena、Carmen Ramírez de Arellano

  DOI：10.1021/jo701484w

  日期：2007.11.1

  The synthesis of new chiral fluorinated amino and azamacrolactones of types 1 and 2 is described. A ring-closing metathesis (RCM) reaction constitutes the key step in this methodology, which uses fluorinated amino alcohols 7 as starting materials. The influence of the CF2 group, which is located in the (x-position relative to the carbon bearing the amino group, on the efficiency of the RCM reaction is noteworthy. This method allows for the preparation of the desired fluorinated macrolactones in excellent yields.