1,1,2-tribromo-2-(4-methylphenoxy)methylcyclopropane | 244056-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,1,2-tribromo-2-(4-methylphenoxy)methylcyclopropane
• 英文别名: 1-Methyl-4-[(1,2,2-tribromocyclopropyl)methoxy]benzene
• CAS: 244056-21-1
• 化学式: C₁₁H₁₁Br₃O
• 分子量: 398.92
• InChiKey: VNSYKLZOUGHXOX-UHFFFAOYSA-N

物化性质

• 沸点：
  362.8±37.0 °C(Predicted)
• 密度：
  2.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  1,1,2-tribromo-2-(4-methylphenoxy)methylcyclopropane 在 甲基锂 作用下， 以 四氢呋喃 为溶剂， 生成 1-bromo-2-[(4-methylphenoxy)methyl]cyclopropene
  参考文献：
  名称：

  Synthesis and Trapping of Some Substituted 1-Bromocyclopropenes

  摘要：

  Treatment of a number of 2-substituted 1,1,2-tribromocyclopropanes with MeLi at -78 degrees C gave the corresponding 1-bromocyclopropenes, which were reacted with three cyclic dienes to yield the [4 + 2]-cycloadducts. Cycloaddition with 1,3-diphenylisobenzofuran (DPIBF) gave the exo adducts, in most cases in excellent yield, whereas cyclopentadiene afforded endo adducts only, but in moderate yield. In most reactions with furan no adduct was formed, but two 1-bromocyclopropenes derivatives with an aromatic side chain were exceptions and furnished mixtures of exo and endo adducts in moderate yields.

  DOI：

  10.1007/s00706-006-0441-0
• 作为产物：
  描述：

  三溴甲烷 、 2-bromo-3-(4-methylphenoxy)propene 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 水 为溶剂， 以67%的产率得到1,1,2-tribromo-2-(4-methylphenoxy)methylcyclopropane
  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