2-bromo-4-iodo-1-butene | 171779-50-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2-bromo-4-iodo-1-butene
• 英文别名: 2-Bromo-4-iodobut-1-ene
• CAS: 171779-50-3
• 化学式: C₄H₆BrI
• 分子量: 260.9
• InChiKey: XTRHELNCOAVOBU-UHFFFAOYSA-N

物化性质

• 沸点：
  186.5±33.0 °C(Predicted)
• 密度：
  2.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  6
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-bromo-4-iodo-1-butene 、 丙二酸二乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以40%的产率得到diethyl (2-bromobutenyl)malonate
  参考文献：
  名称：

  Cu（I）催化的活化亚甲基化合物与乙烯基卤化物的分子内CC偶联：官能化亚烷基环丁烷的有效合成。

  摘要：

  在CuI / L-脯氨酸的催化下，许多2-（3-溴丁-3-烯基）丙二酸酯进行了有效的分子内C-乙烯基化，从而合成了官能化的亚烷基环丁烷。竞争实验表明，与相应的五元环封闭相比，这种四元环封闭从根本上更受青睐。

  DOI：

  10.1021/ol802012q
• 作为产物：
  描述：

  4-碘-1-丁炔 生成 2-bromo-4-iodo-1-butene
  参考文献：
  名称：

  Conformational Control in the Cyclization of an Unsaturated Vinyllithium: Synthesis of (.+-.)-Laurene

  摘要：

  The olefinic vinyllithium 2, derived from 2-bromo-5-methyl-5-(4-methylphenyl)-1,6-heptadiene (3) by low-temperature lithium-bromine exchange, undergoes a diastereoselective B-exo cyclization at 0 degrees C in the presence of TMEDA to afford the naturally occurring sesquiterpene (+/-)-laurene (1) in 60% isolated yield along with 17% of the isomeric (+/-)-epilaurene (4). The diastereoselectivity of the cyclization of 2 is discussed in terms of a transition state for the process that approximates a chair cyclohexane which preferentially adopts a conformation having a pseudoaxial p-tolyl moiety and a pseudoequatorial methyl group at the geminally substituted carbon. In contrast to the behavior of 2, radical-mediated cyclization of 3 proceeds entirely in a 6-endo fashion to give 4-methyl-4-(4-methylphenyl)-1-methylenecyclohexan (6) in 93% yield.

  DOI：

  10.1021/jo00129a020

文献信息

• Synthesis of tryptophan derivatives via a palladium-catalyzed N-heteroannulation
  作者：Christopher A. Dacko、Novruz G. Akhmedov、Björn C.G. Söderberg

  DOI：10.1016/j.tetasy.2008.10.032

  日期：2008.12

  Tryptophan derivatives were prepared from 2-(2-nitrophenyl)-2-propen-1-yl substituted pyrazines, derived from Schöllkopf’s chiral auxiliary, using a palladium-catalyzed, carbon monoxide-mediated reductive N-heteroannulation reaction. A diastereomeric ratio of products ranging from 4:1 to >30:1 was observed.

  使用钯催化的一氧化碳介导的还原性N-杂环化反应，由衍生自Schöllkopf手性助剂的2-（2-硝基苯基）-2-丙烯-1-基取代的吡嗪制备色氨酸衍生物。观察到产物的非对映异构体比率为4：1至> 30：1。
• Tandem radical nitrile transfer-cyclization reactions of 1,3-dioxane-4-nitriles: Synthesis of spirocyclic systems
  作者：Scott D. Rychnovsky、Sonja S. Swenson

  DOI：10.1016/s0040-4020(97)01030-2

  日期：1997.12

  Reduction of remote halogen substituents with n-Bu3SnH leads to efficient 1,4- and 1,5-nitrile transfer from 1,3-dioxane-4-nitriles and subsequent stereoselective reduction. These radical-transfer reactions provide a mild alternative to the Li/NH3 reductive decyanation previously used to generate syn-1,3-diols from 1,3-dioxane-4-nitriles. Compounds containing appropriate unsaturation undergo subsequent radical cyclization reactions to give spirocyclic products. (C) 1997 Elsevier Science Ltd.