4-(tert-butoxycarbonylamino)but-2-ynyl benzoate | 917365-40-3

• 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: 4-(tert-butoxycarbonylamino)but-2-ynyl benzoate
• 英文别名: 4-[(2-Methylpropan-2-yl)oxycarbonylamino]but-2-ynyl benzoate
• CAS: 917365-40-3
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: CQVXFRYDNLNWOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(tert-butoxycarbonylamino)but-2-ynyl benzoate 在 [RuCl₂(=CHPh)(PCy)3)2] 三乙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 1.66h， 生成 (R)-2-(1-((4-bromophenyl)sulfonyl)-5-((tert-butoxycarbonyl)amino)-1,2,5,6-tetrahydropyridin-3-yl)allyl benzoate
  参考文献：
  名称：

  An Oligomer-Based Approach to Skeletal Diversity in Small-Molecule Synthesis

  摘要：

  Access to small molecules of widely varying molecular shapes has been identified as an enabling step in the discovery of biologically active materials. In this communication we introduce an approach to the systematic development of architecturally distinct chemical compounds based upon the assembly of reactive monomers into linear oligomers, each of which encodes a unique molecular framework under a common set of reaction conditions. Certain products of the initial chemical transformation (Ru-catalyzed metathesis reaction) encode additional skeletons upon treatment with a second common set of reagents (Diels-Alder dienophiles). Application of this oligomerization approach has led to the discovery of a previously unreported tandem ene-yne-yne metathesis-6pi-electrocyclization-1,5-hydride migration that converts a linear substrate into a complex tricyclic 1,3-diene in a single step. Thus, the reported strategy might serve not only as a generator of skeletally diverse small molecules but also as a discovery platform for the identification of novel chemical transformations.

  DOI：

  10.1021/ja065724a
• 作为产物：
  描述：

  N-(叔丁氧羰基)-2-硝基苯酰胺 在 吡啶 、 lithium hydroxide 、 巯基乙酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 53.75h， 生成 4-(tert-butoxycarbonylamino)but-2-ynyl benzoate
  参考文献：
  名称：

  An Oligomer-Based Approach to Skeletal Diversity in Small-Molecule Synthesis

  摘要：

  Access to small molecules of widely varying molecular shapes has been identified as an enabling step in the discovery of biologically active materials. In this communication we introduce an approach to the systematic development of architecturally distinct chemical compounds based upon the assembly of reactive monomers into linear oligomers, each of which encodes a unique molecular framework under a common set of reaction conditions. Certain products of the initial chemical transformation (Ru-catalyzed metathesis reaction) encode additional skeletons upon treatment with a second common set of reagents (Diels-Alder dienophiles). Application of this oligomerization approach has led to the discovery of a previously unreported tandem ene-yne-yne metathesis-6pi-electrocyclization-1,5-hydride migration that converts a linear substrate into a complex tricyclic 1,3-diene in a single step. Thus, the reported strategy might serve not only as a generator of skeletally diverse small molecules but also as a discovery platform for the identification of novel chemical transformations.

  DOI：

  10.1021/ja065724a

文献信息

• Total Synthesis of <i>ent</i>-Plagiochianin B
  作者：Richard K. Jackson、John L. Wood

  DOI：10.1021/acs.orglett.0c04219

  日期：2021.2.19

  An enantioselective total synthesis of plagiochianin B is described that employs (+)-3-carene as its point of departure and delivers the enantiomer of the natural product. Key features of the synthesis include a palladium-mediated regioselective oxidative cleavage of an olefin residing on a pyridine derived from a 6π-azatriene electrocyclization.

  描述了一种对映选择性全合成 plagiochianin B，它采用 (+)-3-carene 作为其出发点并提供天然产物的对映异构体。该合成的关键特征包括钯介导的区域选择性氧化裂解位于 6π-氮杂三烯电环化衍生的吡啶上的烯烃。
• An Oligomer-Based Approach to Skeletal Diversity in Small-Molecule Synthesis
  作者：David A. Spiegel、Frank C. Schroeder、Jeremy R. Duvall、Stuart L. Schreiber

  DOI：10.1021/ja065724a

  日期：2006.11.1

  Access to small molecules of widely varying molecular shapes has been identified as an enabling step in the discovery of biologically active materials. In this communication we introduce an approach to the systematic development of architecturally distinct chemical compounds based upon the assembly of reactive monomers into linear oligomers, each of which encodes a unique molecular framework under a common set of reaction conditions. Certain products of the initial chemical transformation (Ru-catalyzed metathesis reaction) encode additional skeletons upon treatment with a second common set of reagents (Diels-Alder dienophiles). Application of this oligomerization approach has led to the discovery of a previously unreported tandem ene-yne-yne metathesis-6pi-electrocyclization-1,5-hydride migration that converts a linear substrate into a complex tricyclic 1,3-diene in a single step. Thus, the reported strategy might serve not only as a generator of skeletally diverse small molecules but also as a discovery platform for the identification of novel chemical transformations.