(S)-6,6'-dibromo-2,2'-binaphtho-20-crown | 55442-72-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-6,6'-dibromo-2,2'-binaphtho-20-crown
• 英文别名: (+/-)-22,27-dibromo-4,5,7,8,10,11,13,14,16,17-decahydrodinaphtho<2,1-q:1',2'-s><1,4,7,10,13,16>hexaoxacycloicosin；6,33-dibromo-12,15,18,21,24,27-hexaoxapentacyclo[26.8.0.02,11.03,8.031,36]hexatriaconta-1(28),2(11),3(8),4,6,9,29,31(36),32,34-decaene
• CAS: 55442-72-3
• 化学式: C₃₀H₃₀Br₂O₆
• 分子量: 646.373
• InChiKey: NJWFKDFVWZOYIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  38
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  4-乙烯基吡啶 、 (S)-6,6'-dibromo-2,2'-binaphtho-20-crown 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以72%的产率得到R(a)-2,2'-(pentaethylene glycol)-1,1'-binaphthalene-6,6'-bis(4-vinylpyridine)
  参考文献：
  名称：

  Interlocked Chiral Nanotubes Assembled from Quintuple Helices

  摘要：

  Homochiral helical chains were rationally synthesized from C2-symmetric 1,1-binaphthyl-6,6'-bipyridine ligands and linear metal-connecting points, Ni(acac)2. Five such homochiral helices associate in parallel to form nanotubes of 2 x 2 nm in dimensions which further intertwine to form periodically ordered, interlocked nanotubular architectures that possess nanometer-scale open channels and have high affinity for aromatic molecules. Chiral crown ethers have also been successfully incorporated into the walls of these nanotubes, which promises to lead to novel chiral zeolitic materials applicable in enantioselective processes.

  DOI：

  10.1021/ja029926s
• 作为产物：
  描述：

  (S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol 、 二对甲苯磺酸戊乙二醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 (S)-6,6'-dibromo-2,2'-binaphtho-20-crown
  参考文献：
  名称：

  手性1,1'-联萘基分子裂隙用于兴奋性氨基酸衍生物的络合

  摘要：

  的络合ñ -苄氧羰基（Cbz）的兴奋性氨基酸的氨基酸衍生物L-天冬氨酸（Asp; 1），L-谷氨酸（谷氨酸; 3），并且，在第一时间，L-红藻氨酸（（2-小号，3 S，3 S）-2-羧基-4-（1-甲基乙烯基）吡咯烷-3-乙酸; Kai; 5）在CDCl 3中进行了研究，该混合物具有由1,1'-联萘基组成的多种手性受体具有（羧酰胺基）吡啶（CONH（py））官能团的间隔基连接到主凹槽的6,6'-位。A型受体具有两个N-（吡啶-2-基）羧酰胺H键位（例如7），而B型受体具有两个连接的N-（吡啶-6,2-二基）乙酰胺残基（例如8和9）。兴奋性氨基酸衍生物与其他非手性α，β-二羧酸与这些受体的配合物主要通过两组CO··HN和OH··N H键稳定。旋光性A型受体（如（R）-和（S）-7显示出对较大的Glu衍生物的偏好，而B型受体（如（R）-和（S）-8和（R）-和（小号） - 9与较小的Cbz-A

  DOI：

  10.1002/hlca.19950780502

文献信息

• Chiral 1,1?-Binaphthyl Molecular Clefts for the Complexation of Excitatory Amino-Acid Derivatives
  作者：Esther Martinborough、Tiziana Mordasini Denti、Peter P. Castro、Tara B. Wyman、Carolyn B. Knobler、Fran�ois Diederich

  DOI：10.1002/hlca.19950780502

  日期：1995.8.9

  as (R)- and (S)-7 showed a preference for the larger Glu derivative, whereas type-B receptors such as (R)- and (S)-8 and (R)- and (S)-9 formed more stable complexes with the smaller Cbz-Asp. To improve the poor enantioselectivity shown by 7–9, additional functionality was introduced at the 7,7′-positions of the 1,1′-binaphthyl spacer, and the nature of the H-bonding sites in the 6,6′-positions was varied

  的络合ñ -苄氧羰基（Cbz）的兴奋性氨基酸的氨基酸衍生物L-天冬氨酸（Asp; 1），L-谷氨酸（谷氨酸; 3），并且，在第一时间，L-红藻氨酸（（2-小号，3 S，3 S）-2-羧基-4-（1-甲基乙烯基）吡咯烷-3-乙酸; Kai; 5）在CDCl 3中进行了研究，该混合物具有由1,1'-联萘基组成的多种手性受体具有（羧酰胺基）吡啶（CONH（py））官能团的间隔基连接到主凹槽的6,6'-位。A型受体具有两个N-（吡啶-2-基）羧酰胺H键位（例如7），而B型受体具有两个连接的N-（吡啶-6,2-二基）乙酰胺残基（例如8和9）。兴奋性氨基酸衍生物与其他非手性α，β-二羧酸与这些受体的配合物主要通过两组CO··HN和OH··N H键稳定。旋光性A型受体（如（R）-和（S）-7显示出对较大的Glu衍生物的偏好，而B型受体（如（R）-和（S）-8和（R）-和（小号） - 9与较小的Cbz-A
• 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.
• Interlocked Chiral Nanotubes Assembled from Quintuple Helices
  作者：Yong Cui、Suk Joong Lee、Wenbin Lin

  DOI：10.1021/ja029926s

  日期：2003.5.1

  Homochiral helical chains were rationally synthesized from C2-symmetric 1,1-binaphthyl-6,6'-bipyridine ligands and linear metal-connecting points, Ni(acac)2. Five such homochiral helices associate in parallel to form nanotubes of 2 x 2 nm in dimensions which further intertwine to form periodically ordered, interlocked nanotubular architectures that possess nanometer-scale open channels and have high affinity for aromatic molecules. Chiral crown ethers have also been successfully incorporated into the walls of these nanotubes, which promises to lead to novel chiral zeolitic materials applicable in enantioselective processes.