(Z)-4-Bromo-4-hexen-3-one | 134891-16-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-4-Bromo-4-hexen-3-one
• 英文别名: (4Z)-4-bromo-4-hexen-3-one；(Z)-4-bromohex-4-en-3-one
• CAS: 134891-16-0
• 化学式: C₆H₉BrO
• 分子量: 177.041
• InChiKey: CLMCVDJPNABWMJ-HYXAFXHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-己炔-2-醇 在 N-溴代丁二酰亚胺(NBS) 、 silver tetrafluoroborate 作用下， 以 various solvent(s) 为溶剂， 以80%的产率得到(Z)-4-Bromo-4-hexen-3-one
  参考文献：
  名称：

  α-Haloenones from secondary alkynols

  摘要：

  alpha-Iodoenones and alpha-bromoenones are formed from secondary alkynols by the use of the appropriate N-halosuccinimide and a catalytic amount of certain Lewis acids. For example, 3-hexyn-2-ol (1) was converted to (Z)-4-iodo-4-hexen-3-one (2) in 85-95% yields with an equimolar quantity of NIS and tenth molar (hydroxy (toxyloxy) iodo) benzene (3) in methanol or 1-methyl-2-pyrrolididone.

  DOI：

  10.1016/s0040-4039(00)71246-9

文献信息

• SYNTHESIS OF ALPHA-HALO ENONES AND ENALS
  申请人：Zhang Liming

  公开号：US20110021806A1

  公开（公告）日：2011-01-27

  A method for preparing an α-halo enal or enone from an unprotected propargyl alcohol and an electrophilic halogen source catalyzed by the combination of a gold catalyst complex and a metal co-catalyst complex is disclosed. The method can be further enhanced by addition of an additive that facilitates suppression of a des-halo derivative.

  本发明公开了一种通过金催化剂配合金属共催化剂，从未保护的丙炔醇和电泳卤素源制备α-卤代烯醇或烯酮的方法。该方法可以通过添加有助于抑制去卤代衍生物的添加剂来进一步增强。
• US8269047B2
  申请人：——

  公开号：US8269047B2

  公开（公告）日：2012-09-18
• α-Haloenones from secondary alkynols
  作者：Geetha J. Angara、Edward McNelis

  DOI：10.1016/s0040-4039(00)71246-9

  日期：1991.5

  alpha-Iodoenones and alpha-bromoenones are formed from secondary alkynols by the use of the appropriate N-halosuccinimide and a catalytic amount of certain Lewis acids. For example, 3-hexyn-2-ol (1) was converted to (Z)-4-iodo-4-hexen-3-one (2) in 85-95% yields with an equimolar quantity of NIS and tenth molar (hydroxy (toxyloxy) iodo) benzene (3) in methanol or 1-methyl-2-pyrrolididone.