1,1-dibromo-4-(p-tolyl)-1-buten-3-yne | 919087-42-6

• 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: 1,1-dibromo-4-(p-tolyl)-1-buten-3-yne
• 英文别名: 1-(4,4-dibromobut-3-en-1-ynyl)-4-methylbenzene
• CAS: 919087-42-6
• 化学式: C₁₁H₈Br₂
• 分子量: 299.993
• InChiKey: XGNOFLWJMFAUGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,1-dibromo-4-(p-tolyl)-1-buten-3-yne 在 丁二酰亚胺 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以65%的产率得到1-(buta-1,3-diyn-1-yl)-4-methylbenzene
  参考文献：
  名称：

  干反应条件下炔烃的合成

  摘要：

  开发了一种简单的合成方法，该方法在干燥反应条件下由1,1-二溴烯烃制备丁炔，并在作为亲核试剂和质子供体的琥珀酰亚胺存在下制备。广泛的末端炔烃的合成证明了这一点，并在串联反应条件下扩展到合成内部炔烃。

  DOI：

  10.1016/j.tetlet.2021.153051
• 作为产物：
  描述：

  四溴化碳 、 (4-甲基苯基)炔丙醛 在 2,6-二甲基吡啶 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1,1-dibromo-4-(p-tolyl)-1-buten-3-yne
  参考文献：
  名称：

  Highly Efficient and Selective Synthesis of Conjugated Triynes and Higher Oligoynes of Biological and Materials Chemical Interest via Palladium-Catalyzed Alkynyl−Alkenyl Coupling

  摘要：

  Iteration of a Pd-catalyzed reaction of alkynyl- and oligoynylzincs with (E)-ICH-CHCI followed by metalation-termination with electrophiles(E) has provided a linear route to conjugated tri- and tetraynes, and Pd-catalyzed monoalkynylation of 1,1-dibromoenynes accompanied by dehydrobromination has provided a convergent route to conjugated tri-, tetra-, and pentaynes. Both display unprecedented high efficiency and selectivity.

  DOI：

  10.1021/ol0623825

文献信息

• De Novo Synthesis of Tricyclic 5,5-Benzannulated Spiroketals
  作者：Maddali L. N. Rao、Sk Shamim Islam

  DOI：10.1021/acs.orglett.1c01109

  日期：2021.5.21

  The synthesis of tricyclic 5,5-benzannulated spiroketal scaffolds was accomplished from 2′-hydroxyacetophenones and gem-dibromoalkenes involving a one-pot domino strategy. The hitherto unknown transformation afforded the tricyclic 5,5-benzannulated spiroketals as single diastereomers in high yields with a broad substrate scope.

  三环5,5-苯基环化的螺缩酮骨架的合成从2'-羟基苯乙完成和宝石-dibromoalkenes涉及一釜骨牌策略。迄今未知的转化以高收率和广泛的底物范围提供了三环5,5-苯甲酰化螺环酮，为单一非对映异构体。
• Synthesis of alkynes under dry reaction conditions
  作者：Maddali L.N. Rao、Sk Shamim Islam

  DOI：10.1016/j.tetlet.2021.153051

  日期：2021.5

  method was developed under dry reaction conditions for the preparation of terminal alkynes from 1,1-dibromoalkenes and in the presence of succinimide which acts as a nucleophile and proton donor. It was demonstrated with the synthesis of a broad spectrum of terminal alkynes and extended to synthesize internal alkynes under tandem reaction conditions.

  开发了一种简单的合成方法，该方法在干燥反应条件下由1,1-二溴烯烃制备丁炔，并在作为亲核试剂和质子供体的琥珀酰亚胺存在下制备。广泛的末端炔烃的合成证明了这一点，并在串联反应条件下扩展到合成内部炔烃。
• Highly Efficient and Selective Synthesis of Conjugated Triynes and Higher Oligoynes of Biological and Materials Chemical Interest via Palladium-Catalyzed Alkynyl−Alkenyl Coupling
  作者：Estelle Métay、Qian Hu、Ei-ichi Negishi

  DOI：10.1021/ol0623825

  日期：2006.12.1

  Iteration of a Pd-catalyzed reaction of alkynyl- and oligoynylzincs with (E)-ICH-CHCI followed by metalation-termination with electrophiles(E) has provided a linear route to conjugated tri- and tetraynes, and Pd-catalyzed monoalkynylation of 1,1-dibromoenynes accompanied by dehydrobromination has provided a convergent route to conjugated tri-, tetra-, and pentaynes. Both display unprecedented high efficiency and selectivity.