5-(1-戊炔-1-基)嘧啶 | 202828-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-(1-戊炔-1-基)嘧啶
• 英文名称: 5-Pent-1-ynylpyrimidine
• CAS: 202828-83-9
• 化学式: C₉H₁₀N₂
• 分子量: 146.192
• InChiKey: LIDZNYAVBUGJNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  diethylzinc 、 5-(1-戊炔-1-基)嘧啶 在 N-甲基吡咯烷酮 、 bis(acetylacetonate)nickel(II) 、 碘 作用下， 生成 5-((E)-2-Ethyl-1-iodo-pent-1-enyl)-pyrimidine 、 5-((Z)-2-Ethyl-1-iodo-pent-1-enyl)-pyrimidine
  参考文献：
  名称：

  A nickel-catalyzed carbozincation of aryl-substituted alkynes

  摘要：

  The addition of dialkylzincs or diphenylzinc to substituted phenylacetylenes in the presence of catalytic amounts of Ni(acac)(2) in THF : NMP mixtures produces syn-carbozincation products with good to excellent regio-and stereoselectivity. After quenching with an electrophile (iodine, acyl chloride, allyl bromide) tetrasubstituted olefines are obtained in good to satisfactory yields. An intramolecular version of the reaction is possible using a terminal triple bond bearing an iodine at a remote position. More substituted iodo-alkynes furnish only reductive elimination products. An application to a stereoselective synthesis of (Z)-tamoxifen (Z: E > 99: 1) has been developed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10226-5
• 作为产物：
  描述：

  5-溴嘧啶 、 1-戊炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 作用下， 以 二乙胺 为溶剂， 反应 20.0h， 以77%的产率得到5-(1-戊炔-1-基)嘧啶
  参考文献：
  名称：

  A nickel-catalyzed carbozincation of aryl-substituted alkynes

  摘要：

  The addition of dialkylzincs or diphenylzinc to substituted phenylacetylenes in the presence of catalytic amounts of Ni(acac)(2) in THF : NMP mixtures produces syn-carbozincation products with good to excellent regio-and stereoselectivity. After quenching with an electrophile (iodine, acyl chloride, allyl bromide) tetrasubstituted olefines are obtained in good to satisfactory yields. An intramolecular version of the reaction is possible using a terminal triple bond bearing an iodine at a remote position. More substituted iodo-alkynes furnish only reductive elimination products. An application to a stereoselective synthesis of (Z)-tamoxifen (Z: E > 99: 1) has been developed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10226-5

文献信息

• A nickel-catalyzed carbozincation of aryl-substituted alkynes
  作者：Thomas Stüdemann、Malika Ibrahim-Ouali、Paul Knochel

  DOI：10.1016/s0040-4020(97)10226-5

  日期：1998.2

  The addition of dialkylzincs or diphenylzinc to substituted phenylacetylenes in the presence of catalytic amounts of Ni(acac)(2) in THF : NMP mixtures produces syn-carbozincation products with good to excellent regio-and stereoselectivity. After quenching with an electrophile (iodine, acyl chloride, allyl bromide) tetrasubstituted olefines are obtained in good to satisfactory yields. An intramolecular version of the reaction is possible using a terminal triple bond bearing an iodine at a remote position. More substituted iodo-alkynes furnish only reductive elimination products. An application to a stereoselective synthesis of (Z)-tamoxifen (Z: E > 99: 1) has been developed. (C) 1998 Elsevier Science Ltd. All rights reserved.