1-(Benzenesulfonyl)-3-[bis(4-fluorophenyl)methylidene]-2-prop-2-enylpiperidine

• 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: 1-(Benzenesulfonyl)-3-[bis(4-fluorophenyl)methylidene]-2-prop-2-enylpiperidine
• 英文别名: 1-(benzenesulfonyl)-3-[bis(4-fluorophenyl)methylidene]-2-prop-2-enylpiperidine
• 化学式: C₄H₈NO₃Pol
• 分子量: 465.6
• InChiKey: GHMGJNSTGRORKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(Benzenesulfonyl)-3-[bis(4-fluorophenyl)methylidene]-2-prop-2-enylpiperidine 、 在 吡啶 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Solid-phase based synthesis of biologically promising triazolyl aminoacyl (peptidyl) penicillins

  摘要：

  An efficient and versatile methodology for the preparation of valuable triazolyl aminoacyl (peptidyl) penicillins is described. Solid-phase Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition was used as the key step showing general applicability and excellent regioselectivity either with CuI or [Cu(CH3CN)(4)]PF6 as Cu(I) source. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.113
• 作为产物：
  描述：

  在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(Benzenesulfonyl)-3-[bis(4-fluorophenyl)methylidene]-2-prop-2-enylpiperidine
  参考文献：
  名称：

  Solid-phase based synthesis of biologically promising triazolyl aminoacyl (peptidyl) penicillins

  摘要：

  An efficient and versatile methodology for the preparation of valuable triazolyl aminoacyl (peptidyl) penicillins is described. Solid-phase Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition was used as the key step showing general applicability and excellent regioselectivity either with CuI or [Cu(CH3CN)(4)]PF6 as Cu(I) source. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.113

文献信息

• Synthesis and Evaluation of a Dipeptide–Drug Conjugate Library As Substrates for PEPT1
  作者：Lihui Zhang、Li Zhang、Tian Luo、Jie Zhou、Lingyi Sun、Yuhong Xu

  DOI：10.1021/co200141b

  日期：2012.2.13

  The oligopeptide transporter PEPT1 is considered as a valuable target for prodrug design, but its 3D structure and substrate specificity of PEPT1 are not fully understood. In this study, we designed a focused dipeptide 'conjugated azidothymidine (AZT) library and described a convenient and efficient solid phase synthesis scheme based on click chemistry Over 60 candidate structures containing various dipeptide sequences were obtained with high purity, and screened in a PEPT1 overexpressing cell model for their abilities to compete with the known ligand: cephalexin. Some of the compounds selected to have medium or high affinity were tested for their in vivo transport in a single-pass, intestinal perfusion experiment Results showed that the designed library contained some new structure features that have,high affinities toward PEPT1 and could be further explored for their application in prodrug design and development.
• Regioselective synthesis of 2-substituted 3-diarylmethylenylpiperidines
  作者：Meng-Yang Chang、Chung-Han Lin、Tein-Wei Lee

  DOI：10.1016/j.tetlet.2011.11.105

  日期：2012.2

  A simple three-step synthetic routes toward 2-substituted 3-diarylmethylenylpiperidines 7 (Y = CN) and 8 (Y = allyl) starting with 3-diarylmethylenylpiperidines 9 is described. The process was carried out by the bromomethoxylation of skeleton 9 with NBS in MeOH at reflux for 2 h, regioselective alpha-dehydrobromination with DBU in THF at reflux for 10 h, and BF3-OEt(2)catalyzed cross-coupling of the corresponding enamine with trimethylsilyl-based nucleophiles (TMS-Y) in DCM at rt for 2 h. alpha-Amino ester 18 and beta-amino acid 19 are also synthesized via the simple three-step synthetic protocol. (C) 2011 Elsevier Ltd. All rights reserved.
• Solid-phase based synthesis of biologically promising triazolyl aminoacyl (peptidyl) penicillins
  作者：Patricia G. Cornier、Dora B. Boggián、Ernesto G. Mata、Carina M.L. Delpiccolo

  DOI：10.1016/j.tetlet.2011.11.113

  日期：2012.2

  An efficient and versatile methodology for the preparation of valuable triazolyl aminoacyl (peptidyl) penicillins is described. Solid-phase Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition was used as the key step showing general applicability and excellent regioselectivity either with CuI or [Cu(CH3CN)(4)]PF6 as Cu(I) source. (C) 2011 Elsevier Ltd. All rights reserved.