(5Z)-1-benzyl-5-benzylidenepiperidin-3-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (5Z)-1-benzyl-5-benzylidenepiperidin-3-ol
• 英文别名: (Z)-1-benzyl-5-benzylidenepiperidin-3-ol
• 化学式: C₁₉H₂₁NO
• 分子量: 279.382
• InChiKey: JHWTZRGXSHTBHM-WQRHYEAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苄基-2-丙炔胺 在 bis(1,5-cyclooctadiene)nickel (0) 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙基硼 、 三丁基膦 、 potassium carbonate 、 三乙胺 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 39.5h， 生成 (5Z)-1-benzyl-5-benzylidenepiperidin-3-ol
  参考文献：
  名称：

  Nickel-Catalyzed Reductive Coupling of Alkynes and Epoxides

  摘要：

  Nickel-catalyzed, intramolecular and intermolecular reductive coupling of alkynes and epoxides affords synthetically useful homoallylic alcohols of defined alkene geometry. Very high regioselectivity is generally observed, and cyclizations proceed with complete selectivity for endo epoxide opening. This catalytic reaction represents the first use of a non-pi-based electrophile in a growing class of nickel-catalyzed, multicomponent coupling reactions, and is the first catalytic method of reductive coupling of alkynes and epoxides that is effective for both intermolecular and intramolecular cases, and mechanistically distinct from these, possibly involving a nickella(II)oxetane.

  DOI：

  10.1021/ja0361401

文献信息

• Ni(II) Salts and 2-Propanol Effect Catalytic Reductive Coupling of Epoxides and Alkynes
  作者：Matthew G. Beaver、Timothy F. Jamison

  DOI：10.1021/ol201702a

  日期：2011.8.5

  A Ni-catalyzed reductive coupling of alkynes and epoxides using Ni(II) salts and simple alcohol reducing agents is described. Whereas previously reported conditions relied on Ni(cod)2 and Et3B, this system has several advantages including the use of air-stable and inexpensive Ni(II) precatalysts (e.g., NiBr2·3H2O) as the source of Ni(0) and simple alcohols (e.g., 2-propanol) as the reducing agent.

  描述了使用 Ni(II) 盐和简单的醇还原剂对炔烃和环氧化物进行 Ni 催化的还原偶联。尽管之前报道的条件依赖于 Ni(cod) 2和 Et 3 B，但该系统具有几个优点，包括使用空气稳定且价格低廉的 Ni(II) 预催化剂（例如 NiBr 2 ·3H 2 O）作为 Ni 的来源(0) 和简单的醇（例如，2-丙醇）作为还原剂。氘标记实验与随着构型反转发生的环氧化物 C-O 键的氧化加成一致。
• Nickel-Catalyzed Reductive Coupling of Alkynes and Epoxides
  作者：Carmela Molinaro、Timothy F. Jamison

  DOI：10.1021/ja0361401

  日期：2003.7.1

  Nickel-catalyzed, intramolecular and intermolecular reductive coupling of alkynes and epoxides affords synthetically useful homoallylic alcohols of defined alkene geometry. Very high regioselectivity is generally observed, and cyclizations proceed with complete selectivity for endo epoxide opening. This catalytic reaction represents the first use of a non-pi-based electrophile in a growing class of nickel-catalyzed, multicomponent coupling reactions, and is the first catalytic method of reductive coupling of alkynes and epoxides that is effective for both intermolecular and intramolecular cases, and mechanistically distinct from these, possibly involving a nickella(II)oxetane.