(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。
• C2-Symmetric Bisphosphine Ligands Derived from 1,1′-Binaphthyldiamines and Diphenylphosphinobenzoic Acid for Palladium Catalyzed Desymmetrizations
  作者：Chung Woo Lim、Sang-gi Lee

  DOI：10.1016/s0040-4020(00)00420-8

  日期：2000.7

  A series of novel C-2-symmetric bisphosphine ligands derived from DPPBA and C-2-symmetric 1,1'-binaphthyldiamines has been synthesized. In palladium catalyzed desymmetrization of meso cyclic carbamates, the enantioselectivity and the stereochemistry of the major enantiomers are largely affected by the substitution position of DPPBA moiety on the 1,1'-binaphthyl chiral scaffold. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 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：——