6-(3,4-dichlorophenyl)-1-[(methyloxy)methyl]-3-[(2-nitrophenyl)sulfonyl]-3-azabicyclo[4.1.0]hept-4-ene

• 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: 6-(3,4-dichlorophenyl)-1-[(methyloxy)methyl]-3-[(2-nitrophenyl)sulfonyl]-3-azabicyclo[4.1.0]hept-4-ene
• 英文别名: (1S,6R)-6-(3,4-dichlorophenyl)-1-(methoxymethyl)-3-(2-nitrophenyl)sulfonyl-3-azabicyclo[4.1.0]hept-4-ene
• 化学式: C₂₀H₁₈Cl₂N₂O₅S
• 分子量: 469.345
• InChiKey: DJAJQHWHDYTNIK-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(3,4-dichlorophenyl)-1-[(methyloxy)methyl]-3-[(2-nitrophenyl)sulfonyl]-3-azabicyclo[4.1.0]hept-4-ene 在 DL-半胱氨酸 、 三乙基硅烷 、 三氟乙酸 作用下， 以 水 、 甲苯 为溶剂， 反应 4.0h， 以84.8%的产率得到6-(3,4-dichlorophenyl)-1-[(methyloxy)methyl]-3-[(2-nitrophenyl)sulfonyl]-3-azabicyclo[4.1.0]heptane
  参考文献：
  名称：

  An Enyne Cycloisomerization Approach to the Triple Reuptake Inhibitor GSK1360707F

  摘要：

  The triple reuptake inhibitor GSK1360707F was synthesized via an efficient and scalable route that features an enyne cycloisomerization reaction catalyzed by either Pt(II) or Au(I). Key aspects of this work such as the choice of the nitrogen protecting group and initial en-antioselectivity studies are discussed.

  DOI：

  10.1021/jo102098y
• 作为产物：
  描述：

  2-nitro-N-(prop-2-yn-1-yl)benzenesulfonamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 、 platinum(II) chloride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.33h， 生成 6-(3,4-dichlorophenyl)-1-[(methyloxy)methyl]-3-[(2-nitrophenyl)sulfonyl]-3-azabicyclo[4.1.0]hept-4-ene
  参考文献：
  名称：

  An Enyne Cycloisomerization Approach to the Triple Reuptake Inhibitor GSK1360707F

  摘要：

  The triple reuptake inhibitor GSK1360707F was synthesized via an efficient and scalable route that features an enyne cycloisomerization reaction catalyzed by either Pt(II) or Au(I). Key aspects of this work such as the choice of the nitrogen protecting group and initial en-antioselectivity studies are discussed.

  DOI：

  10.1021/jo102098y

文献信息

• Effects of nitrogen and alkene substitution on the PtCl2 catalyzed cycloisomerization of N-tethered 1,6-enyne precursors to the triple reuptake inhibitor GSK1360707
  作者：Vassil Elitzin、Bing Liu、Matthew Sharp、Elie Tabet

  DOI：10.1016/j.tetlet.2011.05.005

  日期：2011.7

  The effects of nitrogen and alkene substitution on the cycloisomerization of N-tethered 1,6-enynes into 3-azabicyclo[4.1.0]Theptene precursors to the triple reuptake inhibitor GSK1360707 are described. In general, electron donating substituents proved beneficial both in terms of the reaction rate and chemoselectivity. (C) 2011 Elsevier Ltd. All rights reserved.
• An Enyne Cycloisomerization Approach to the Triple Reuptake Inhibitor GSK1360707F
  作者：Nicole M. Deschamps、Vassil I. Elitzin、Bing Liu、Mark B. Mitchell、Matthew J. Sharp、Elie A. Tabet

  DOI：10.1021/jo102098y

  日期：2011.1.21

  The triple reuptake inhibitor GSK1360707F was synthesized via an efficient and scalable route that features an enyne cycloisomerization reaction catalyzed by either Pt(II) or Au(I). Key aspects of this work such as the choice of the nitrogen protecting group and initial en-antioselectivity studies are discussed.