(S_p)-4-amino-12-trifluoromethanesulfonyloxy[2.2]paracyclophane

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (S_p)-4-amino-12-trifluoromethanesulfonyloxy[2.2]paracyclophane
• 英文别名: (11-Amino-5-tricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaenyl) trifluoromethanesulfonate；(11-amino-5-tricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaenyl) trifluoromethanesulfonate
• 化学式: C₁₇H₁₆F₃NO₃S
• 分子量: 371.38
• InChiKey: ASSWGAGJEHNQGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S_p)-4-amino-12-trifluoromethanesulfonyloxy[2.2]paracyclophane 、 3,5-二甲氧基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 12.0h， 以89%的产率得到(Sp)-4-amino-12-(3,5-dimethoxyphenyl)[2.2]paracyclophane
  参考文献：
  名称：

  Synthesis of planar chiral pseudo–ortho-substituted aryl[2.2]paracyclophanes by stepwise successive palladium-catalyzed coupling reactions

  摘要：

  Planar chiral aryl[2.2]paracyclophanyl-thioureas and -phosphine with a pseudo-ortho substitution pattern have been designed and efficiently synthesized by stepwise successive palladium-catalyzed crosscoupling reactions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.05.023
• 作为产物：
  描述：

  (Sp)-12-bromo[2.2]paracyclophan-4-yl trifluoromethanesulfonate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三叔丁基膦 、 sodium phenoxide 、 三氟乙酸 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 34.0h， 生成 (S_p)-4-amino-12-trifluoromethanesulfonyloxy[2.2]paracyclophane
  参考文献：
  名称：

  Synthesis of planar chiral pseudo–ortho-substituted aryl[2.2]paracyclophanes by stepwise successive palladium-catalyzed coupling reactions

  摘要：

  Planar chiral aryl[2.2]paracyclophanyl-thioureas and -phosphine with a pseudo-ortho substitution pattern have been designed and efficiently synthesized by stepwise successive palladium-catalyzed crosscoupling reactions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.05.023

文献信息

• Synthesis of new alkoxy/sulfonate-substituted carbene precursors derived from [2.2]paracyclophane and their application in the asymmetric arylation of aldehydes
  作者：Wenzeng Duan、Yudao Ma、Bo Qu、Lei Zhao、Jianqiang Chen、Chun Song

  DOI：10.1016/j.tetasy.2012.09.001

  日期：2012.10

  A series of novel planar chiral alkoxy/sulfonate-substituted carbene precursors have been designed and synthesized. They were used as N-heterocyclic carbene ligands in the Rh-catalyzed asymmetric addition of arylboronic acids to aromatic aldehydes, affording chiral diarylmethanols with high yields and moderate enantioselectivities. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of planar chiral pseudo–ortho-substituted aryl[2.2]paracyclophanes by stepwise successive palladium-catalyzed coupling reactions
  作者：Shinji Kitagaki、Yuu Ohta、Shoichirou Tomonaga、Ryohei Takahashi、Chisato Mukai

  DOI：10.1016/j.tetasy.2011.05.023

  日期：2011.5

  Planar chiral aryl[2.2]paracyclophanyl-thioureas and -phosphine with a pseudo-ortho substitution pattern have been designed and efficiently synthesized by stepwise successive palladium-catalyzed crosscoupling reactions. (C) 2011 Elsevier Ltd. All rights reserved.