1-[2,2-Bis(bromomethyl)-3-(4-methylphenyl)propyl]-4-methylbenzene | 1046446-06-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-[2,2-Bis(bromomethyl)-3-(4-methylphenyl)propyl]-4-methylbenzene
• 英文别名: 1-[2,2-bis(bromomethyl)-3-(4-methylphenyl)propyl]-4-methylbenzene
• CAS: 1046446-06-3
• 化学式: C₁₉H₂₂Br₂
• 分子量: 410.192
• InChiKey: WJYOLURODPWUNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 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-[2,2-Bis(bromomethyl)-3-(4-methylphenyl)propyl]-4-methylbenzene 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到1,1-bis(p-methylbenzyl)cyclopropane
  参考文献：
  名称：

  Radical 3-exo-tet cyclization of 1,3-dihalopropanes with SmI2 to form cyclopropanes

  摘要：

  The preparation of 1,1-disubstituted and monosubstituted cycloproparres from corresponding 2,2-disubstituted and 2-monosubstituted 1,3-dihalopropanes, respectively, with SMI2 in THF was efficiently carried out. The reaction mechanism was proposed to proceed in a radical 3-exo-tet manner based on Baldwin's rule. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.081
• 作为产物：
  描述：

  2,2-Bis[(4-methylphenyl)methyl]propane-1,3-diol 在 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 1-[2,2-Bis(bromomethyl)-3-(4-methylphenyl)propyl]-4-methylbenzene
  参考文献：
  名称：

  Radical 3-exo-tet cyclization of 1,3-dihalopropanes with SmI2 to form cyclopropanes

  摘要：

  The preparation of 1,1-disubstituted and monosubstituted cycloproparres from corresponding 2,2-disubstituted and 2-monosubstituted 1,3-dihalopropanes, respectively, with SMI2 in THF was efficiently carried out. The reaction mechanism was proposed to proceed in a radical 3-exo-tet manner based on Baldwin's rule. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.081

文献信息

• Radical 3-exo-tet cyclization of 1,3-dihalopropanes with SmI2 to form cyclopropanes
  作者：Tsuyoshi Ohkita、Yuhsuke Tsuchiya、Hideo Togo

  DOI：10.1016/j.tet.2008.05.081

  日期：2008.7

  The preparation of 1,1-disubstituted and monosubstituted cycloproparres from corresponding 2,2-disubstituted and 2-monosubstituted 1,3-dihalopropanes, respectively, with SMI2 in THF was efficiently carried out. The reaction mechanism was proposed to proceed in a radical 3-exo-tet manner based on Baldwin's rule. (c) 2008 Elsevier Ltd. All rights reserved.
• 3-exo-tet Cyclization of 2,2-disubstituted 1,3-dihalopropanes with indium in aqueous and ionic liquid solvent system
  作者：Yuhsuke Tsuchiya、Yuhta Izumisawa、Hideo Togo

  DOI：10.1016/j.tet.2009.06.123

  日期：2009.9

  The 3-exo-tet cyclization of 2,2-disubstituted 1,3-dihalopropanes with In powder in THF solution of 20% H2O, dioxane solution of 20% H2O, and ionic liquids, such as [bmim]Br, [bmim]Cl, and [bmin]BF4, respectively, was efficiently carried out to form the corresponding 1,1-disubstituted cyclopropanes in good yields. The cyclopropanation of 2,2-disubstituted 1,3-dihalopropanes with In powder in ionic liquids, such as [bmim]Br, [bmim]Cl, and [bmin]BF4, was markedly accelerated compared with that in a THF solution of 20% H2O and a dioxane solution of 20% H2O. The mechanism was proposed to involve the radical 3-exo-tet cyclization of the formed 3-halopropyl radical. (C) 2009 Elsevier Ltd. All rights reserved.