meso-2,2-dimethyl-4,5-bis(2-bromophenyl)-1,3-dioxolane | 1115639-85-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: meso-2,2-dimethyl-4,5-bis(2-bromophenyl)-1,3-dioxolane
• 英文别名: (4S,5R)-4,5-bis(2-bromophenyl)-2,2-dimethyl-1,3-dioxolane
• CAS: 1115639-85-4
• 化学式: C₁₇H₁₆Br₂O₂
• 分子量: 412.121
• InChiKey: LEPZQCAVCSCMHG-IYBDPMFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  meso-2,2-dimethyl-4,5-bis(2-bromophenyl)-1,3-dioxolane 在 正丁基锂 、 calcium hydride 、 鹰爪豆碱 、 重水 作用下， 以 正己烷 、 甲苯 为溶剂， 以72%的产率得到4-(2-bromophenyl)-5-(2-deuterophenyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Two aspects of the desymmetrization of selected prochiral aromatic or vinylic dihalides: enantioselective halogen–lithium exchange and prochiral recognition in chiral liquid crystals

  摘要：

  Several classes of prochiral dihalides have been identified as potential candidates for asymmetric halogen-lithium exchange. Bis-aryl compounds I and 2, 2,3-dibromonorbornadiene 3, and 1,2-diiodoferrocene 4 were prepared and used as substrates in the asymmetric halogen-lithium exchange reaction. The enantioselective mono-lithiation was achieved in good yields by various combinations of n-BuLi and chiral ligands. Enantioselectivities in the range of 20-35% ee have been detected for this new type of asymmetric synthesis. The prochiral compounds 3 and 4 were also dissolved in a chiral liquid crystal based on organic solutions of poly-gamma-benzyl-L-glutamate and analyzed using natural abundance deuterium 2D NMR spectroscopy. The spectroscopic discrimination of enantiotopic sites in these solutes has been observed and discussed from the point of view of orientational order. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.003
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 1,2-乙二醇,1,2-二(2-溴苯基)-,(1R,2S)-rel- 在 对甲苯磺酸 作用下， 以 正己烷 为溶剂， 反应 6.5h， 以95%的产率得到meso-2,2-dimethyl-4,5-bis(2-bromophenyl)-1,3-dioxolane
  参考文献：
  名称：

  Two aspects of the desymmetrization of selected prochiral aromatic or vinylic dihalides: enantioselective halogen–lithium exchange and prochiral recognition in chiral liquid crystals

  摘要：

  Several classes of prochiral dihalides have been identified as potential candidates for asymmetric halogen-lithium exchange. Bis-aryl compounds I and 2, 2,3-dibromonorbornadiene 3, and 1,2-diiodoferrocene 4 were prepared and used as substrates in the asymmetric halogen-lithium exchange reaction. The enantioselective mono-lithiation was achieved in good yields by various combinations of n-BuLi and chiral ligands. Enantioselectivities in the range of 20-35% ee have been detected for this new type of asymmetric synthesis. The prochiral compounds 3 and 4 were also dissolved in a chiral liquid crystal based on organic solutions of poly-gamma-benzyl-L-glutamate and analyzed using natural abundance deuterium 2D NMR spectroscopy. The spectroscopic discrimination of enantiotopic sites in these solutes has been observed and discussed from the point of view of orientational order. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.003

文献信息

• Two aspects of the desymmetrization of selected prochiral aromatic or vinylic dihalides: enantioselective halogen–lithium exchange and prochiral recognition in chiral liquid crystals
  作者：Chun-An Fan、Benoît Ferber、Henri B. Kagan、Olivier Lafon、Philippe Lesot

  DOI：10.1016/j.tetasy.2008.12.003

  日期：2008.12

  Several classes of prochiral dihalides have been identified as potential candidates for asymmetric halogen-lithium exchange. Bis-aryl compounds I and 2, 2,3-dibromonorbornadiene 3, and 1,2-diiodoferrocene 4 were prepared and used as substrates in the asymmetric halogen-lithium exchange reaction. The enantioselective mono-lithiation was achieved in good yields by various combinations of n-BuLi and chiral ligands. Enantioselectivities in the range of 20-35% ee have been detected for this new type of asymmetric synthesis. The prochiral compounds 3 and 4 were also dissolved in a chiral liquid crystal based on organic solutions of poly-gamma-benzyl-L-glutamate and analyzed using natural abundance deuterium 2D NMR spectroscopy. The spectroscopic discrimination of enantiotopic sites in these solutes has been observed and discussed from the point of view of orientational order. (C) 2008 Elsevier Ltd. All rights reserved.