1-((4-bromophenyl)buta-1,3-diyn-1-yl)cyclohexanol | 1342819-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((4-bromophenyl)buta-1,3-diyn-1-yl)cyclohexanol
• CAS: 1342819-66-2
• 化学式: C₁₆H₁₅BrO
• 分子量: 303.198
• InChiKey: FFKRVBXTIIOBDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-((4-bromophenyl)buta-1,3-diyn-1-yl)cyclohexanol 在 二氧化碳 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 90.0 ℃ 、2.0 MPa 条件下， 反应 36.0h， 以80%的产率得到2-(4-bromobenzyl)-1-oxaspiro[4.5]dec-2-en-4-one
  参考文献：
  名称：

  Carbon dioxide-mediated synthesis of 3(2H)-furanones from diyne alcohols

  摘要：

  A novel type of carbon dioxide-mediated reaction of diyne alcohols without any metal catalysts was reported. Carbon dioxide held the key to the success of this reaction, in which 3(2H)-furanones were selectively obtained in moderate to high yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.130
• 作为产物：
  描述：

  (4-溴苯基)乙炔 在 N-溴代丁二酰亚胺(NBS) 、 盐酸羟胺 、 silver nitrate 、 正丁胺 、 copper(l) chloride 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 1-((4-bromophenyl)buta-1,3-diyn-1-yl)cyclohexanol
  参考文献：
  名称：

  Carbon dioxide-mediated synthesis of 3(2H)-furanones from diyne alcohols

  摘要：

  A novel type of carbon dioxide-mediated reaction of diyne alcohols without any metal catalysts was reported. Carbon dioxide held the key to the success of this reaction, in which 3(2H)-furanones were selectively obtained in moderate to high yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.130

文献信息

• Nonafluorobutanesulfonyl Azide as a Shelf-Stable Highly Reactive Oxidant for the Copper-Catalyzed Synthesis of 1,3-Diynes from Terminal Alkynes
  作者：José Ramón Suárez、Daniel Collado-Sanz、Diego J. Cárdenas、Jose Luis Chiara

  DOI：10.1021/jo5025909

  日期：2015.1.16

  Nonafluorobutanesulfonyl azide is a highly efficient reagent for the copper-catalyzed coupling of terminal alkynes to give symmetrical and unsymmetrical 1,3-diynes in good to excellent yields and with good functional group compatibility. The reaction is extremely fast (<10 min), even at low temperature (-78 degrees C), and requires substoichiometric amounts of a simple copper(I) or copper(II) salt (2-5 mol %) and an organic base (0.6 mol %). A possible mechanistic pathway is briefly discussed on the basis of model DFT theoretical calculations. The quantitative assessment of the safety of use and shelf stability of nonafluorobutanesulfonyl azide has confirmed that this reagent is a superior and safe alternative to other electrophilic azide reagents in use today.