(R)-(-)-7,7'-Bis(benzyloxy)-2,2'-dimethoxy-1,1'-binaphthyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-(-)-7,7'-Bis(benzyloxy)-2,2'-dimethoxy-1,1'-binaphthyl
• 英文别名: 2-Methoxy-1-(2-methoxy-7-phenylmethoxynaphthalen-1-yl)-7-phenylmethoxynaphthalene
• 化学式: C₃₆H₃₀O₄
• 分子量: 526.632
• InChiKey: WAROCCFXWAYNKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(-)-7,7'-Bis(benzyloxy)-2,2'-dimethoxy-1,1'-binaphthyl 在 palladium on activated charcoal 氢气 、 甲酸铵 作用下， 以31%的产率得到(R)-(-)-7-Mono(benzyloxy)-7'-monohydroxy-2,2'-dimethoxy-1,1'-binaphthyl
  参考文献：
  名称：

  Chiral recognition in clefts and cyclophane cavities shaped by the 1,1'-binaphthyl major groove

  摘要：

  DOI：

  10.1021/jo00286a003
• 作为产物：
  描述：

  (R)-7,7-bis(benzyloxy)-2,2'-dihydroxy-1,1'-binaphthyl 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到(R)-(-)-7,7'-Bis(benzyloxy)-2,2'-dimethoxy-1,1'-binaphthyl
  参考文献：
  名称：

  Synthesis of (R)- and (S)-7,7′-bis(diphenylphosphino)-2,2′-dimethoxy-1,1′-binaphthyl, a new axially dissymmetric bis(triarylphosphine)

  摘要：

  A new axially dissymmetric bis(triarylphosphine) ligand 7,7'-bis(diphenylphosphino)-2,2'-dimethoxy-1,1'-binaphthyl has been synthesized in enantiomerically pure form.

  DOI：

  10.1016/s0957-4166(00)86197-2

文献信息

• Optically active diphosphine, transition metal complex containing the
  申请人：Takasago International Corporation

  公开号：US05789609A1

  公开（公告）日：1998-08-04

  Disclosed are an optically active diphosphine represented by formula: ##STR1## wherein R represents a lower alkyl group having 1 to 4 carbon atoms; Ar represents a phenyl group which may be substituted with a lower alkyl group having 1 to 4 carbon atoms and/or a lower alkoxy group having 1 to 4 carbon atoms, a transition metal complex containing the diphosphine as a ligand, and a process for producing an optically active .delta.-oxo-.alpha.-cyano ester using the transition metal complex as a catalyst.

  本发明涉及一种光学活性的二膦化合物，其表示为以下公式：##STR1## 其中R代表1至4个碳原子的低碳基团；Ar代表苯基，其可以被取代为1至4个碳原子的低碳基团和/或1至4个碳原子的低烷氧基团。本发明还涉及一种以该二膦化合物为配体的过渡金属配合物，以及一种使用该过渡金属配合物作为催化剂制备光学活性的δ-氧代-α-氰基酯的方法。
• Optically active diphosphine, transition metal complex containing the same, and process for producing optically active compound using the complex
  申请人：Takasago International Corporation

  公开号：EP0839818A1

  公开（公告）日：1998-05-06

  Disclosed are an optically active diphosphine represented by formula: wherein R represents a lower alkyl group having 1 to 4 carbon atoms; Ar represents a phenyl group which may be substituted with a lower alkyl group having 1 to 4 carbon atoms and/or a lower alkoxy group having 1 to 4 carbon atoms, a transition metal complex containing the diphosphine as a ligand, and a process for producing an optically active δ-oxo-α-cyano ester using the transition metal complex as a catalyst.

  本发明公开了一种由式表示的光学活性二膦： 其中 R 代表具有 1 至 4 个碳原子的低级烷基；Ar 代表可被具有 1 至 4 个碳原子的低级烷基和/或具有 1 至 4 个碳原子的低级烷氧基取代的苯基、 含有二膦作为配位体的过渡金属络合物，以及使用该过渡金属络合物作为催化剂生产光学活性 δ-氧代-α-氰基酯的工艺。
• Synthesis of (R)- and (S)-7,7′-bis(diphenylphosphino)-2,2′-dimethoxy-1,1′-binaphthyl, a new axially dissymmetric bis(triarylphosphine)
  作者：Toshihide Horiuchi、Tetsuo Ohta、Massoud Stephan、Hidemasa Takaya

  DOI：10.1016/s0957-4166(00)86197-2

  日期：1994.3

  A new axially dissymmetric bis(triarylphosphine) ligand 7,7'-bis(diphenylphosphino)-2,2'-dimethoxy-1,1'-binaphthyl has been synthesized in enantiomerically pure form.
• Chiral Recognition of Cinchona Alkaloids at the Minor and Major Grooves of 1,1'-Binaphthyl Receptors
  作者：Jon Reeder、Peter P. Castro、Carolyn B. Knobler、Esther Martinborough、Linda Owens、Francois Diederich

  DOI：10.1021/jo00090a037

  日期：1994.6

  A variety of chiral 1,1'-binaphthyl derivatives with one or two hydroxyl groups at either the 2,2'-(minor groove) or the 7,7'-positions (major groove) were prepared for enantioselective recognition of the cinchona alkaloids quinine and quinidine. The study was initiated when it was found that (+/-)-7,7'-bis(benzyloxy)-2,2'-dihydroxy-1,1'-binaphthyl ((+/-)-1a) was readily resolved through simple clathrate formation with quinine and quinidine. Optical resolution of (+/-)-1a was also achieved by fractional crystallization of its cyclic phosphate ester with quinidine. The absolute configuration of the optically pure binaphthyl derivatives was established by transformation of (-)-1a into a binaphthyl derivative of known absolute configuration (R) through reactions of defined stereochemistry. The X-ray crystal structure analysis of the (S)-(+)-1a.quinidine complex showed that ion pairing is the major interaction between the two components. Complexation of quinine and quinidine at both major and minor grooves of the 1,1'-binaphthyl derivatives occurred in CDCl3 with a significant degree of chiral recognition, and differences in stability between diastereomeric complexes were as large as Delta(Delta G degrees) approximate to 1 kcal mol(-1) (293 K). Quinine is consistently better bound by the (R)-receptors whereas quinidine always prefers the (S)-enantiomers. The structures of the complexes, which are stabilized by hydrogen-bonding and aromatic-aromatic interactions, were analyzed on the basis of the complexation-induced changes in H-1 NMR chemical shifts of the binding partners at saturation binding Delta delta(sat), H-1H-1} nuclear Overhauser effects (NOEs), and molecular modeling.
• CASTO, PETER P.;GEORGIADIS, TAXIARCHIS M.;DIEDERICH, FRANCOIS, J. ORG. CHEM., 54,(1989) N5, C. 5835-5838
  作者：CASTO, PETER P.、GEORGIADIS, TAXIARCHIS M.、DIEDERICH, FRANCOIS

  DOI：——

  日期：——