2-bromo-3-(4-chlorophenoxy)propene | 244056-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-bromo-3-(4-chlorophenoxy)propene
• 英文别名: 1-((2-bromoallyl)oxy)-4-chlorobenzene；1-(2-Bromoprop-2-enoxy)-4-chlorobenzene
• CAS: 244056-17-5
• 化学式: C₉H₈BrClO
• 分子量: 247.519
• InChiKey: XSDBAPITNYYTGP-UHFFFAOYSA-N

物化性质

• 沸点：
  292.9±25.0 °C(Predicted)
• 密度：
  1.486±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-3-(4-chlorophenoxy)propene 在 sodium hydroxide 、 苄基三乙基氯化铵 、 (三溴甲基)苯汞 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 生成 3,3-diethoxy-4-(4-chlorophenoxy)-1-butyne
  参考文献：
  名称：

  Neighbouring-group Influence on the Ring Opening of 2-Aryloxymethyl-1,1,2-tribromocyclopropanes under Phase-transfer Conditions.

  摘要：

  When a number of 2-aryloxymethyl-1,1,2-tribromocyclopropa were treated with sodium hydroxide and ethanol under phase-transfer conditions, ring opening occurred to give mixtures of acetylenic diethyl acetals and ketals in better than 80% total isolated yield. The acetylenic diethyl ketals predominated significantly and were, in some cases, almost the exclusive product. It is argued that this ketal selectivity is in part caused by hydrogen bonding between ethanol and the aryloxy group.

  DOI：

  10.3891/acta.chem.scand.53-0465
• 作为产物：
  描述：

  4-氯-烯丙氧基 在 pyridinium hydrobromide perbromide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以94%的产率得到2-bromo-3-(4-chlorophenoxy)propene
  参考文献：
  名称：

  烯丙醇衍生物区域选择性溴化和顺序碳-碳键形成反应的一锅法

  摘要：

  已经开发了一种有效的一锅法，用于烯丙醇衍生物的区域选择性溴化（两步反应顺序），然​​后在同一反应容器中进行 Sonogashira、Negishi 或 Suzuki-Miyaura 偶联反应（三步反应顺序）。这些一锅系统中的关键反应是区域选择性 DBU 促进的反式 HBr 消除带有相邻 O 官能团的邻位二溴化物。

  DOI：

  10.1002/ejoc.201300173

文献信息

• Conversion of 3-<i>O</i>-Substituted 1,2-Dibromoalkanes into 2-Bromo-1-alkenes by the Selective Elimination: Its Application to Total Synthesis of 12-Oxygenated Tremetones
  作者：Tadaaki Ohgiya、Shigeru Nishiyama

  DOI：10.1246/cl.2004.1084

  日期：2004.9

  2-Bromo-1-alkenes were efficiently synthesized in good yields by the regioselective HBr-elimination reaction of 3-aryloxy- or 3-acyloxy-1,2-dibromoalkanes. Total synthesis of several oxygenated tremetones has been accomplished by using the 2-bromo-1-alkene derivative produced by this elimination reaction.

  通过 3-芳氧基-或 3-酰氧基-1,2-二溴烷烃的区域选择性 HBr 消除反应，2-溴-1-烯烃以良好的产率有效合成。通过使用该消除反应产生的 2-bromo-1-烯烃衍生物，已经完成了几种含氧曲美酮的全合成。
• TBAF-Promoted Elimination of Vicinal Dibromides Having an Adjacent O-Functional Group: Syntheses of 2-Bromoalk-1-enes and Alkynes
  作者：Noriki Kutsumura、Takao Saito、Keisuke Kubokawa

  DOI：10.1055/s-0030-1260089

  日期：2011.8

  2-bromoalk-1-enes and alkynes were achieved in good yields by dehydrobromination of vicinal dibromides with tetrabutylammonium fluoride. Neighboring O-functional-group participation is important in determining elimination reactivity. tetrabutylammonium fluoride - elimination - 2-bromo­alk-1-enes - alkynes - vicinal dibromides

  通过用氟化四丁基铵将邻位二溴化物脱氢溴化，可以高收率地合成2-溴烷基-1-烯和炔烃。相邻的O-官能团的参与对于确定消除反应性很重要。 四丁基氟化铵-消除-2-溴烷基-1-烯-炔烃-邻二溴化物
• TBAF-Promoted Dehydrobrominations of Vicinal Dibromides Having an Adjacent O-Functional Group
  作者：Noriki Kutsumura、Takao Saito、Keisuke Kubokawa

  DOI：10.1055/s-0030-1258813

  日期：2010.11

  Regioselective HBr elimination of vicinal dibromides having an adjacent oxygen functional group to give the corresponding 2-bromoalk-1-enes was controlled using 1.1 equivalents of TBAF. Two-step elimination to give the corresponding alkynes was controlled using 5.0 equivalents of TBAF. High yield and high selectivity require the presence of an oxygen functional group at the neighboring position of the elimination site.

  使用 1.1 当量的 TBAF 可控制具有相邻氧官能团的邻位二溴化物的区域选择性 HBr 消去，得到相应的 2-溴烷基-1-烯。使用 5.0 等量的 TBAF 可以控制两步消去生成相应的炔烃。高产率和高选择性要求在消除位点的邻近位置存在氧官能团。
• Electrochemical Reductive Cross-Coupling of Vinyl Bromides for the Synthesis of 1,3-Dienes
  作者：Hong Zhang、Zenghui Ye、Yanqi Wu、Xi Zhang、Weiyuan Ma、Zha-Jun Zhan、Fengzhi Zhang

  DOI：10.1021/acs.orglett.3c03940

  日期：2024.2.9

  An electroreductive cross-electrophile coupling protocol was developed for the construction of valuable 1,3-dienes from vinyl bromides. Furthermore, this scalable method can also be used to forge complex [4 + 2] cycloadducts in a one-pot manner. One of the most important advantages of this green and sustainable protocol is the in situ release of nickel catalyst from the inexpensive electrodes without

  开发了一种电还原交叉亲电子偶联方案，用于从溴化乙烯构建有价值的 1,3-二烯。此外，这种可扩展的方法还可用于以一锅法制备复杂的[4 + 2]环加合物。这种绿色和可持续协议最重要的优点之一是从廉价的电极中原位释放镍催化剂，而不添加额外的有害金属催化剂和还原剂。
• Novel One-Pot Method for Chemoselective Bromination and Sequential Sonogashira Coupling
  作者：Noriki Kutsumura、Kentaro Niwa、Takao Saito

  DOI：10.1021/ol101110v

  日期：2010.8.6

  An efficient one-pot method for bromination-elimination of allyl alcohol derivatives and sequential Sonogashira coupling has been developed. A highlight of the method is chemoselective DBU-promoted elimination of vicinal dibromoalkanes having an adjacent O-functional group.