benzyl 2,6-difluoro-4-[(1E)-3-hydroxyprop-1-enyl]phenylacrylate | 777089-85-7

• 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: benzyl 2,6-difluoro-4-[(1E)-3-hydroxyprop-1-enyl]phenylacrylate
• 英文别名: benzyl N-[3,5-difluoro-4-[(E)-3-hydroxyprop-1-enyl]phenyl]carbamate
• CAS: 777089-85-7
• 化学式: C₁₇H₁₅F₂NO₃
• 分子量: 319.308
• InChiKey: DTTPCGDIFIVPTF-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  benzyl 2,6-difluoro-4-[(1E)-3-hydroxyprop-1-enyl]phenylacrylate 在 bis(N-tert-butylsalicylaldiminato)copper(II) 锂硼氢 、 1-氯-N,N,2-三甲基丙烯胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 0.67h， 生成 [4-((1S,2R,3S)-2,3-Bis-hydroxymethyl-cyclopropyl)-3,5-difluoro-phenyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of Aza-, Oxa-, and Thiabicyclo[3.1.0]hexane Heterocycles from a Common Synthetic Intermediate

  摘要：

  An efficient and stereospecific approach to the synthesis of structurally constrained aza-, oxa-, and thiabicyclo[3.1.0]hexane heterocycles has been achieved through application of the intramolecular cyclopropanation reaction of diazoacetates. The various constrained heterocycles (X = N, O, or S) are conveniently prepared from a common diol intermediate accessible from readily available cinnamyl alcohols. Application of the methodology to the synthesis of conformationally constrained oxazolidinone antibacterials is also discussed.

  DOI：

  10.1021/ol050730h
• 作为产物：
  描述：

  3,5-二氟苯胺 在 吡啶 、 正丁基锂 、 三甲基氯硅烷 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 23.42h， 生成 benzyl 2,6-difluoro-4-[(1E)-3-hydroxyprop-1-enyl]phenylacrylate
  参考文献：
  名称：

  Synthesis of Aza-, Oxa-, and Thiabicyclo[3.1.0]hexane Heterocycles from a Common Synthetic Intermediate

  摘要：

  An efficient and stereospecific approach to the synthesis of structurally constrained aza-, oxa-, and thiabicyclo[3.1.0]hexane heterocycles has been achieved through application of the intramolecular cyclopropanation reaction of diazoacetates. The various constrained heterocycles (X = N, O, or S) are conveniently prepared from a common diol intermediate accessible from readily available cinnamyl alcohols. Application of the methodology to the synthesis of conformationally constrained oxazolidinone antibacterials is also discussed.

  DOI：

  10.1021/ol050730h

文献信息

• US7279494B2
  申请人：——

  公开号：US7279494B2

  公开（公告）日：2007-10-09
• Synthesis of Aza-, Oxa-, and Thiabicyclo[3.1.0]hexane Heterocycles from a Common Synthetic Intermediate
  作者：Adam R. Renslo、Hongwu Gao、Priyadarshini Jaishankar、Revathy Venkatachalam、Mikhail F. Gordeev

  DOI：10.1021/ol050730h

  日期：2005.6.1

  An efficient and stereospecific approach to the synthesis of structurally constrained aza-, oxa-, and thiabicyclo[3.1.0]hexane heterocycles has been achieved through application of the intramolecular cyclopropanation reaction of diazoacetates. The various constrained heterocycles (X = N, O, or S) are conveniently prepared from a common diol intermediate accessible from readily available cinnamyl alcohols. Application of the methodology to the synthesis of conformationally constrained oxazolidinone antibacterials is also discussed.