1-(4-hydroxy-4-phenyl-1-butynyl)-1-methoxycyclohexane | 134750-07-5

• 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: 1-(4-hydroxy-4-phenyl-1-butynyl)-1-methoxycyclohexane
• 英文别名: 4-(1-methoxycyclohexyl)-1-phenylbut-3-yn-1-ol
• CAS: 134750-07-5
• 化学式: C₁₇H₂₂O₂
• 分子量: 258.36
• InChiKey: WUCZFVZEOYUIEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  二碘甲烷 、 苯甲醛 、 1-ethynyl-1-methoxy-cyclohexane 生成 1-(4-hydroxy-4-phenyl-1-butynyl)-1-methoxycyclohexane
  参考文献：
  名称：

  Selective mono- and polymethylene homologations of copper reagents using (iodomethyl)zinc iodide

  摘要：

  A wide range of unsaturated aryl-, alkenyl-, alkynylcopper compounds can be selectively homologated by a methylene unit using (iodomethyl)zinc iodide or bis(iodomethyl)zinc. These reactions allow the generation of mixed allylic zinc-copper compounds which can be efficiently trapped with carbonyl compounds. An application to a general preparation of functionalized alpha-methylene-gamma-butyrolactones is described. The homologation of alkynylcoppers with (iodomethyl)zinc iodide allows a one-pot preparation of propargylic copper reagents which in the presence of a carbonyl compound provide various homopropargylic alcohols in excellent yields. In the absence of an electrophile, a clean quadruple methylene homologation of alkynylcoppers occurs to furnish dienic copper reagents. The homologation of other types of copper reagents is also possible, and carbanions at the alpha-position to amines as well as homoenolates of aldehydes or ketones can also be prepared by this method.

  DOI：

  10.1021/jo00062a010

文献信息

• Selective multiple methylene insertion reactions mediated by iodomethylzine iodide: Mechanistic considerations and synthetic applications
  作者：Michael J. Rozema、Paul Knochel

  DOI：10.1016/s0040-4039(00)85980-8

  日期：1991.4

  The reaction of alkynylcoppers 1 with an excess of iodomethylzinc iodide selectively furnishes the quadruple methylene insertion copper organometallics 2 in fair to good yields. The mechanism of the reaction has been investigated and postulated intermediates such as 4 or 8 have been trapped with electrophiles like aldehydes or ketones in excellent yields. A new in situ preparation of propargylic copper

  炔基铜1与过量的碘代甲基碘化锌的反应选择性地以公平至良好的产率提供了四重亚甲基插入铜有机金属化合物2。已经研究了反应的机理，并且假定的中间体（如4或8）已被亲电子试剂（如醛或酮）以优异的产率捕获。已经开发了一种新的就地制备炔丙基铜衍生物4的方法，该方法从易于获得的炔铜化合物开始，从而以80-95％的收率制得了均炔丙基醇。
• Selective mono- and polymethylene homologations of copper reagents using (iodomethyl)zinc iodide
  作者：AchyuthaRao Sidduri、Michael J. Rozema、Paul Knochel

  DOI：10.1021/jo00062a010

  日期：1993.5

  A wide range of unsaturated aryl-, alkenyl-, alkynylcopper compounds can be selectively homologated by a methylene unit using (iodomethyl)zinc iodide or bis(iodomethyl)zinc. These reactions allow the generation of mixed allylic zinc-copper compounds which can be efficiently trapped with carbonyl compounds. An application to a general preparation of functionalized alpha-methylene-gamma-butyrolactones is described. The homologation of alkynylcoppers with (iodomethyl)zinc iodide allows a one-pot preparation of propargylic copper reagents which in the presence of a carbonyl compound provide various homopropargylic alcohols in excellent yields. In the absence of an electrophile, a clean quadruple methylene homologation of alkynylcoppers occurs to furnish dienic copper reagents. The homologation of other types of copper reagents is also possible, and carbanions at the alpha-position to amines as well as homoenolates of aldehydes or ketones can also be prepared by this method.