(-)-(2R)-2-(N-benzyloxycarbonyl)amino-3,3-difluoro-5-hexen-1-ol | 364049-71-8

• 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: (-)-(2R)-2-(N-benzyloxycarbonyl)amino-3,3-difluoro-5-hexen-1-ol
• 英文别名: benzyl N-[(2R)-3,3-difluoro-1-hydroxyhex-5-en-2-yl]carbamate
• CAS: 364049-71-8
• 化学式: C₁₄H₁₇F₂NO₃
• 分子量: 285.291
• InChiKey: MYMGGHDUXBVGBR-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(2R)-2-(N-benzyloxycarbonyl)amino-3,3-difluoro-5-hexen-1-ol 在 Grubbs catalyst first generation 4-二甲氨基吡啶 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.58h， 生成 (-)-(9aR)-9,9-difluoro-5,8,9,9a-tetrahydro-1H-[1,3]oxazolo[3,4-a]azepin-3-one
  参考文献：
  名称：

  Enantioselective Synthesis of Fluorinated α-Amino Acids and Derivatives in Combination with Ring-Closing Metathesis:  Intramolecular π-Stacking Interactions as a Source of Stereocontrol

  摘要：

  [GRAPHICS]Hydride reduction of C=N bonds stereocontrolled by intramolecular m-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta -amino alcohols and alpha -amino acid derivatives, respectively.

  DOI：

  10.1021/ol016087q
• 作为产物：
  描述：

  N-(4-methoxyphenyl)-1-chloro-2,2-difluoro-4-pentenimidoyl chloride 在 2,4,6-三甲基吡啶 、 ammonium cerium(IV) nitrate 、 tetrabutylammonium borohydride 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 乙腈 为溶剂， 反应 13.83h， 生成 (-)-(2R)-2-(N-benzyloxycarbonyl)amino-3,3-difluoro-5-hexen-1-ol
  参考文献：
  名称：

  Enantioselective Synthesis of Fluorinated α-Amino Acids and Derivatives in Combination with Ring-Closing Metathesis:  Intramolecular π-Stacking Interactions as a Source of Stereocontrol

  摘要：

  [GRAPHICS]Hydride reduction of C=N bonds stereocontrolled by intramolecular m-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta -amino alcohols and alpha -amino acid derivatives, respectively.

  DOI：

  10.1021/ol016087q

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.
• Enantioselective Synthesis of Fluorinated α-Amino Acids and Derivatives in Combination with Ring-Closing Metathesis:  Intramolecular π-Stacking Interactions as a Source of Stereocontrol
  作者：Santos Fustero、Antonio Navarro、Belén Pina、Juan García Soler、Ana Bartolomé,、Amparo Asensio、Antonio Simón、Pierfrancesco Bravo、Giovanni Fronza、Alessandro Volonterio、Matteo Zanda

  DOI：10.1021/ol016087q

  日期：2001.8.1

  [GRAPHICS]Hydride reduction of C=N bonds stereocontrolled by intramolecular m-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta -amino alcohols and alpha -amino acid derivatives, respectively.