(R)-3,3'-bis[3,5-bis(trifluoromethyl)phenyl]-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-disulfonimid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-3,3'-bis[3,5-bis(trifluoromethyl)phenyl]-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-disulfonimid
• 英文别名: 10,16-Bis[3,5-bis(trifluoromethyl)phenyl]-12lambda6,14lambda6-dithia-13-azapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(23),2,8,10,15,17-hexaene 12,12,14,14-tetraoxide；10,16-bis[3,5-bis(trifluoromethyl)phenyl]-12λ6,14λ6-dithia-13-azapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(23),2,8,10,15,17-hexaene 12,12,14,14-tetraoxide
• 化学式: C₃₆H₂₅F₁₂NO₄S₂
• 分子量: 827.712
• InChiKey: LQVQGPIBJBAHCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  55
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  (R)-3,3'-bis[3,5-bis(trifluoromethyl)phenyl]-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-disulfonimid 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 邻二氯苯 为溶剂， 反应 15.0h， 以42%的产率得到3,3’-bis[3,5-bis(perfluoropropan-2-yl)phenyl]-1,1’-binaphthalene-2,2’-sulfonimide
  参考文献：
  名称：

  Direct Interconversion of BINOL and H8-BINOL-Based Chiral Brønsted Acids Using Single-Step Red/Ox Manipulations

  摘要：

  A direct single-step hydrogenation of BINOL-based chiral phosphoric acids, N-triflyl phosphoramides, and disulfonimides to the corresponding H8-BINOL Bronsted acids in excellent yields and chemoselectivities is described. In addition, the conditions for the single-step oxidation of H8-BINOL-based Bronsted acids into the corresponding BINOL-based acids have been identified and employed to accomplish these interconversions in 41-81% yield.

  DOI：

  10.1021/acs.orglett.5b01754
• 作为产物：
  描述：

  3,3’-bis[3,5-bis(perfluoropropan-2-yl)phenyl]-1,1’-binaphthalene-2,2’-sulfonimide 在 二氧化铂 、 氢气 作用下， 以 溶剂黄146 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 以98%的产率得到(R)-3,3'-bis[3,5-bis(trifluoromethyl)phenyl]-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-disulfonimid
  参考文献：
  名称：

  Direct Interconversion of BINOL and H8-BINOL-Based Chiral Brønsted Acids Using Single-Step Red/Ox Manipulations

  摘要：

  A direct single-step hydrogenation of BINOL-based chiral phosphoric acids, N-triflyl phosphoramides, and disulfonimides to the corresponding H8-BINOL Bronsted acids in excellent yields and chemoselectivities is described. In addition, the conditions for the single-step oxidation of H8-BINOL-based Bronsted acids into the corresponding BINOL-based acids have been identified and employed to accomplish these interconversions in 41-81% yield.

  DOI：

  10.1021/acs.orglett.5b01754

文献信息

• CHIRAL DISULFONIMIDES
  申请人：List Benjamin

  公开号：US20110313150A1

  公开（公告）日：2011-12-22

  Chiral disulfonimides having the formula I to III, wherein at least one of the groups A and B in the compound of formula I, C and D of the compound in formula II, and E and F of the compound in formula III is a chiral group, or E and F together form a chiral backbone, X is C, Si, O, N or S, and n is 0, 1, 2, 3, 4, 5 or 6, where n is >1 only if X is C, and G is as defined herein, and to the organic salts, metal salts and metal complexes thereof, are suited as NMR shift reagents and as reagents for racemate splitting, and also as chiral Brønsted acid catalysts or chiral Lewis acid catalysts for activating ketones, aldehydes and alkenes, and also as catalysts in the organic synthesis.

  拥有I至III式的手性二磺酰胺，其中在式I化合物中的A和B基团中至少有一个是手性基团，在式II化合物中的C和D以及在式III化合物中的E和F中，E和F可以共同形成一个手性骨架，X为C、Si、O、N或S，n为0、1、2、3、4、5或6，当X为C时n>1，G如本文所定义，并且适用于其有机盐、金属盐和金属配合物，作为NMR位移试剂和对消旋体分离的试剂，还可作为手性Brønsted酸催化剂或手性Lewis酸催化剂，用于活化酮、醛和烯烃，以及作为有机合成中的催化剂。
• US9079869B2
  申请人：——

  公开号：US9079869B2

  公开（公告）日：2015-07-14