4-chlorobutyl propargyl ether | 1002-51-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-chlorobutyl propargyl ether
• 英文别名: 3-(4-chloro-butoxy)-propyne；(4-Chlor-butyl)-(prop-2-inyl)-aether；1-Chloro-4-prop-2-ynoxybutane
• CAS: 1002-51-3
• 化学式: C₇H₁₁ClO
• mdl: MFCD19234547
• 分子量: 146.617
• InChiKey: CXKSSGHSXNEEOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  85 °C(Press: 15 Torr)
• 密度：
  1.0500 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-chlorobutyl propargyl ether 在 吡啶 、 4-二甲氨基吡啶 、 水 、 caesium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 146.0h， 生成 N-4-(2-propynyloxy)butyl-N'-2-(4,4'-dimethoxytrityloxy)ethyl-N'-2-hydroxyethyl oxalamide
  参考文献：
  名称：

  Oligonucleotide Functionalization by a Novel Alkyne-Modified Nonnucleosidic Reagent Obtained by Versatile Building Block Chemistry

  摘要：

  A convenient synthetic strategy has been designed to prepare an alkyne-modified synthon for automated DNA synthesis. It is based on the key O-DMTr-protected 4-(2-hydroxyethyl)morpholin-2,3-dione and building blocks obtained by its functionalization by various aliphatic amines. A respective nonnucleosidic phosphoramidite monomer containing a terminal alkyne in the side-chain was synthesized, and corresponding oligothymidylates incorporating the modification in various positions were prepared. The presence of the alkyne group was confirmed by Cu(I)-catalyzed azidealkyne cycloaddition (CuAAC) between the functionalized oligonucleotide and an azide derivative of 7-nitro-2,1,3-benzoxadiazole.

  DOI：

  10.1080/15257770.2013.787147
• 作为产物：
  描述：

  4-(prop-2-ynyloxy)butan-1-ol 在 氯化亚砜 作用下， 反应 24.0h， 生成 4-chlorobutyl propargyl ether
  参考文献：
  名称：

  Oligonucleotide Functionalization by a Novel Alkyne-Modified Nonnucleosidic Reagent Obtained by Versatile Building Block Chemistry

  摘要：

  A convenient synthetic strategy has been designed to prepare an alkyne-modified synthon for automated DNA synthesis. It is based on the key O-DMTr-protected 4-(2-hydroxyethyl)morpholin-2,3-dione and building blocks obtained by its functionalization by various aliphatic amines. A respective nonnucleosidic phosphoramidite monomer containing a terminal alkyne in the side-chain was synthesized, and corresponding oligothymidylates incorporating the modification in various positions were prepared. The presence of the alkyne group was confirmed by Cu(I)-catalyzed azidealkyne cycloaddition (CuAAC) between the functionalized oligonucleotide and an azide derivative of 7-nitro-2,1,3-benzoxadiazole.

  DOI：

  10.1080/15257770.2013.787147

文献信息

• Copper(I)-Catalyzed Interrupted Click Reaction: Synthesis of Diverse 5-Hetero-Functionalized Triazoles
  作者：Weiguo Wang、Xianglong Peng、Fang Wei、Chen-Ho Tung、Zhenghu Xu

  DOI：10.1002/anie.201509124

  日期：2016.1.11

  The 5‐heterofunctionalized triazoles are important scaffolds in bioactive compounds, but current click reactions (CuAAC) cannot produce these core structures. A copper(I)‐catalyzed interrupted click reaction to access diverse 5‐functionalized triazoles is reported. Various 5‐amino‐, thio‐, and selenotriazoles were readily assembled in one step in high yields. The reaction proceeds under mild conditions

  5杂功能化的三唑是生物活性化合物中的重要支架，但是当前的点击反应（CuAAC）无法产生这些核心结构。据报道，铜（I）催化的间断点击反应可访问各种5官能化的三唑。多种5-氨基，硫代和硒代三唑易于一步一步组装，高收率。反应在温和条件下进行，具有完全的区域选择性。它还具有广泛的底物范围和良好的官能团相容性。
• Duchon d'Engenieres,M. et al., Bulletin de la Societe Chimique de France, 1964, p. 2471 - 2476
  作者：Duchon d'Engenieres,M. et al.

  DOI：——

  日期：——
• TALYBOV, G. M.;GUSEJNOV, M. M.;GUSEJNOV, SH. O.;KARAEV, S. F., DOKL. AN AZSSR, 45,(1989) N, S. 26-29
  作者：TALYBOV, G. M.、GUSEJNOV, M. M.、GUSEJNOV, SH. O.、KARAEV, S. F.

  DOI：——

  日期：——