(R)-6,6'-dibromo-2,2'-bis(methoxyethoxymethyloxy)-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)-6,6'-dibromo-2,2'-bis(methoxyethoxymethyloxy)-1,1'-binaphthyl
• 英文别名: 6-Bromo-1-[6-bromo-2-(2-methoxyethoxymethoxy)naphthalen-1-yl]-2-(2-methoxyethoxymethoxy)naphthalene；6-bromo-1-[6-bromo-2-(2-methoxyethoxymethoxy)naphthalen-1-yl]-2-(2-methoxyethoxymethoxy)naphthalene
• 化学式: C₂₈H₂₈Br₂O₆
• 分子量: 620.335
• InChiKey: CAFLZAOOJNSLEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-6,6'-dibromo-2,2'-bis(methoxyethoxymethyloxy)-1,1'-binaphthyl 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 生成 (R)-2,2'-bis[(2-methoxyethoxy)methoxy]-6,6'-divinyl-1,1'-binaphthyl
  参考文献：
  名称：

  Polystyrene Resins Incorporating BINOL Units: New Materials For Asymmetric Catalysis

  摘要：

  The radical crosslinking polymerization of styrene with (R)-divinyl-BINOL derivatives results in the formation of reticulated polystyrene networks containing protected (R)-BINOL entities at each junction of the polystyrene chains, The generation of polystyrene-immobilized free (R)-BINOL was performed by cleaving the protecting ether groups under acidic conditions. The resulting materials containing optically active BINOL units were tested as chiral ligands in the enantio-selective addition of diethylzinc to benzaldehyde. The catalytic properties of the polymer gels were shown to be highly dependent on the degree of reticulation: in the best cases, the resins incorporating (R)-BINOL units showed activities and selectivities similar to those of molecular (R)-BINOL. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

  DOI：

  10.1002/1099-0690(200301)2003:1<99::aid-ejoc99>3.0.co;2-q
• 作为产物：
  描述：

  (R)-1,1'-Bi-2-naphthol 、 alkaline earth salt of/the/ methylsulfuric acid 在 溴 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (R)-6,6'-dibromo-2,2'-bis(methoxyethoxymethyloxy)-1,1'-binaphthyl
  参考文献：
  名称：

  由（R）-或（S）-联萘酚衍生物制备的功能性手性杂化硅胶

  摘要：

  我们描述了从光学纯的（R）-或（S）-2,2'-dihydroxy-1开始的新功能双-三烷氧基甲硅烷基化联萘酚衍生物I - V的合成，这些衍生物包含受保护的OH基和氰基，吡啶基和氨基甲酸酯官能团，1'-联萘（BINOL）及其随后通过溶胶-凝胶过程转化为杂化硅胶。（R）-I是通过用MEM-氯化物保护（R）-6,6'-二溴-BINOL的羟基，用正丁基锂进行卤素金属交换并将金属化的（R）-BINOL物种与三甲氧基甲硅烷偶联而获得的。（R）-的合成II，（R）-III，（R）-IV和（R）/（S）-V是在乙烯基-三乙氧基硅烷和乙酸钯/三邻甲苯基膦。

  DOI：

  10.1016/s0022-328x(01)00758-6

文献信息

• Hybrid silarylene polysiloxanes incorporating chiral BINOL entities: a new class of polymer with main chain chirality
  作者：Peter Hesemann、Joël J.E. Moreau、Cheng Yixiang

  DOI：10.1016/s0957-4166(02)00146-5

  日期：2002.4

  We describe the synthesis of four new chiral silylated (R)-BINOL precursors by coupling of lithiated BINOL intermediates with chlorosilanes. These chiral precursors were submitted to different polycondensation procedures to give silarylene polysiloxanes A-D with main chain chirality: either by hydrolysis-polycondensation of the bis-chlorosilane precursor I or by Pd-catalyzed cross-dehydrocoupling of bis-hydrosilanes II, III and IV. Both monomers and polymers were characterized by NMR. FT-IR, circular dichroism and polarimetry. Polymers with molecular weights of up to 30,200 gmol(-1) were obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.