(R,4Sp,13Rp)-4-bromo-13-(4-phenyloxazolin-2-yl)[2.2]paracyclophane

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: (R,4Sp,13Rp)-4-bromo-13-(4-phenyloxazolin-2-yl)[2.2]paracyclophane
• 英文别名: (4R)-2-(12-bromo-5-tricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaenyl)-4-phenyl-4,5-dihydro-1,3-oxazole
• 化学式: C₂₅H₂₂BrNO
• 分子量: 432.36
• InChiKey: WYJXIBNBSZRPOF-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R,4Sp,13Rp)-4-bromo-13-(4-phenyloxazolin-2-yl)[2.2]paracyclophane 在 正丁基锂 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 、 正戊烷 为溶剂， 反应 6.5h， 生成
  参考文献：
  名称：

  基于[2.2]对环烷的平面手性咪唑并[1,5- a ]吡啶鎓盐的合成，用于烯酮的不对称β-硼化反应

  摘要：

  合成了新型的平面手性伪锗烷和伪邻恶唑啉取代的[2.2]对环吡啶基咪唑并[1,5- a ]吡啶鎓三氟甲磺酸酯。在基于[2.2]对环环烷的三氟甲磺酸假邻位咪唑并[1,5 - a ]吡啶鎓的合成过程中，分离了4-氨基-12-恶唑啉基[2.2]对环烷的非对映异构体。咪唑并[1,5- a ]吡啶三氟甲烷用作卡宾的前体在铜催化的烯酮的对映选择性共轭β-硼化反应中使用。在一系列配体和底物的初步测试中，我们获得了高达84％的对映选择性。

  DOI：

  10.1016/j.tetasy.2011.06.023
• 作为产物：
  描述：

  12-Bromo-tricyclo[8.2.2.2^4,7]hexadeca-1(13),4,6,10(14),11,15-hexaene-5-carboxylic acid ((R)-2-hydroxy-1-phenyl-ethyl)-amide 在 四氯化碳 、 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 生成 (R,4Sp,13Rp)-4-bromo-13-(4-phenyloxazolin-2-yl)[2.2]paracyclophane
  参考文献：
  名称：

  Synthesis of novel N,O-planar chiral [2,2]paracyclophane ligands and their application as catalysts in the addition of diethylzinc to aldehydes

  摘要：

  A series of novel planar chiral N,O-[2,2]paracyclophane ligands were synthesised and applied as catalysts in the enantioselective addition of diethylzinc to aldehydes. The results indicate that the planar chirality of [2,2]paracyclophane, not the central chirality of the oxazoline, is the dominant stereocontrolling element. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00102-1

文献信息

• Novel planar chiral P,N-[2.2]paracyclophane ligands: synthesis and application in palladium-catalyzed allylic alkylation
  作者：Xun-Wei Wu、Ke Yuan、Wei Sun、Ming-Jie Zhang、Xue-Long Hou

  DOI：10.1016/s0957-4166(02)00790-5

  日期：2003.1

  A series of planar chiral P,N-[2.2]paracyclophane ligands were synthesized and applied in enantio selective palladium-catalyzed allylic alkylation, in which the central chirality of [2.2]paracyclophane is the dominant stereocontrol element. The effect of the substituents attached to the phosphorus atom of these ligands on the yield and stereoselectivity of the reaction was also investigated. (C) 2003 Published by Elsevier Science Ltd.
• Synthesis of novel N,O-planar chiral [2,2]paracyclophane ligands and their application as catalysts in the addition of diethylzinc to aldehydes
  作者：Xun-Wei Wu、Xue-Long Hou、Li-Xin Dai、Ju Tao、Bo-Xun Cao、Jie Sun

  DOI：10.1016/s0957-4166(01)00102-1

  日期：2001.3

  A series of novel planar chiral N,O-[2,2]paracyclophane ligands were synthesised and applied as catalysts in the enantioselective addition of diethylzinc to aldehydes. The results indicate that the planar chirality of [2,2]paracyclophane, not the central chirality of the oxazoline, is the dominant stereocontrolling element. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of planar chiral imidazo[1,5-a]pyridinium salts based on [2.2]paracyclophane for asymmetric β-borylation of enones
  作者：Bing Hong、Yudao Ma、Lei Zhao、Wenzeng Duan、Fuyan He、Chun Song

  DOI：10.1016/j.tetasy.2011.06.023

  日期：2011.5

  Novel planar chiral pseudo-geminal and pseudo-ortho-oxazoline substituted [2.2]paracyclophanyl imidazo[1,5-a]pyridinium triflates were synthesized. During the synthesis of a pseudo-ortho imidazo[1,5-a]pyridinium triflate based on [2.2]paracyclophane, the diastereoisomers of 4-amino-12-oxazolinyl[2.2]paracyclophane were separated. The imidazo[1,5-a]pyridinium triflates were used as carbene precursors

  合成了新型的平面手性伪锗烷和伪邻恶唑啉取代的[2.2]对环吡啶基咪唑并[1,5- a ]吡啶鎓三氟甲磺酸酯。在基于[2.2]对环环烷的三氟甲磺酸假邻位咪唑并[1,5 - a ]吡啶鎓的合成过程中，分离了4-氨基-12-恶唑啉基[2.2]对环烷的非对映异构体。咪唑并[1,5- a ]吡啶三氟甲烷用作卡宾的前体在铜催化的烯酮的对映选择性共轭β-硼化反应中使用。在一系列配体和底物的初步测试中，我们获得了高达84％的对映选择性。