(S)-6-bromo-3,3'-dimethyl-2,2'-dihydroxy-1,1'-binaphthyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-6-bromo-3,3'-dimethyl-2,2'-dihydroxy-1,1'-binaphthyl
• 英文别名: 6-Bromo-1-(2-hydroxy-3-methylnaphthalen-1-yl)-3-methylnaphthalen-2-ol；6-bromo-1-(2-hydroxy-3-methylnaphthalen-1-yl)-3-methylnaphthalen-2-ol
• 化学式: C₂₂H₁₇BrO₂
• 分子量: 393.28
• InChiKey: KHGHJQAUNWJOKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-6-bromo-3,3'-dimethyl-2,2'-dihydroxy-1,1'-binaphthyl 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 咪唑 、 氢氧化钾 、 四丁基氟化铵 、 magnesium 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 277.0h， 生成 10,37-dimethyl-2-(undec-10-en-1-yl)-12,13,15,16,31,32,34,35-octahydrotetranaphtho[2,1-h:1',2'-j:2'',1''-s:1''',2'''-u][1,4,7,12,15,18]hexaoxacyclodocosine
  参考文献：
  名称：

  Monofunctional chiral crowns. Part 1

  摘要：

  A siloxane oligomer bearing a chiral crown with high affinity for alpha-amino acids has been synthesised. The host is a modified form of a coronand first prepared by Cram, in which two 1,1'-binaphthol system are linked through the oxygen atoms at the 2,2'-positions to form a 22-membered ring system containing six ether oxygen atoms attached to each other by four ethylene units. This was selectively mono-alkenylated to form an undec-10-en-1-yl derivative, which was bonded to linear siloxanes [HSiMe2O(SiMe2O)nSiMe2H] and [Me3SiO(Me2SiO)x(MeHSiO)ySiMe3] with total chain lengths of ca 4 and 200 Si atoms respectively, via a Pt catalysed hydrosilylation reaction.

  DOI：

  10.1016/s0040-4020(01)86291-8
• 作为产物：
  描述：

  (S)-6-bromo-3,3'-dimethyl-2-hydroxy-2'-pivaloyloxy-1,1'-binaphthyl 在 二异丁基氢化铝 作用下， 以 乙醚 、 甲苯 为溶剂， 以93%的产率得到(S)-6-bromo-3,3'-dimethyl-2,2'-dihydroxy-1,1'-binaphthyl
  参考文献：
  名称：

  Polymer-carrying optically active binaphthyl type oxazoline compound

  摘要：

  一种携带聚合物的具有轴向不对称性的光学活性联萘基氧唑啉化合物，由下列一般式（1）表示（其中R1和R2可以相同也可以不同，且分别表示氢原子、具有1至6个碳原子的烷基基团或类似物；R3表示氢原子或—R5—X—R6；R4表示氢原子或类似物；R5表示可直接或间接连接的直链或支链脂肪烃链，可能具有直接或间接连接的取代基；X为CH2、CO2、O、CONR7或NR7；R6表示直接或间接连接的聚合物；R7表示氢原子或类似物），以及使用该化合物作为配体的过渡金属配合物。

  公开号：

  US20040097738A1

文献信息

• Polymer-carrying optically active binaphthyl type oxazoline compound
  申请人：Takasago International Corporation

  公开号：US20040097738A1

  公开（公告）日：2004-05-20

  A polymer-carrying optically active binaphthyl type oxazoline compound having axial asymmetry, represented by the following general formula (1) 1 (wherein R 1 and R 2 may be the same or different from each other and each represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms or the like; R 3 is a hydrogen atom or —R 5 —X—R 6 ; R 4 is a hydrogen atom or the like; R 5 is a straight- or branched-chain aliphatic hydrocarbon chain which may have a directly or indirectly bonded substituent; X is CH 2 , CO 2 , O, CONR 7 or NR 7 ; R 6 is a directly or indirectly bonded polymer; and R 7 is a hydrogen atom or the like), and to a transition metal complex which uses the compound as the ligand.

  一种携带聚合物的具有轴向不对称性的光学活性联萘基氧唑啉化合物，由下列一般式（1）表示（其中R1和R2可以相同也可以不同，且分别表示氢原子、具有1至6个碳原子的烷基基团或类似物；R3表示氢原子或—R5—X—R6；R4表示氢原子或类似物；R5表示可直接或间接连接的直链或支链脂肪烃链，可能具有直接或间接连接的取代基；X为CH2、CO2、O、CONR7或NR7；R6表示直接或间接连接的聚合物；R7表示氢原子或类似物），以及使用该化合物作为配体的过渡金属配合物。
• Monofunctional chiral crowns. Part 1
  作者：Brian J. Brisdon、Richard England、Khalid Reza、Malcolm Sainsbury

  DOI：10.1016/s0040-4020(01)86291-8

  日期：1993.1

  A siloxane oligomer bearing a chiral crown with high affinity for alpha-amino acids has been synthesised. The host is a modified form of a coronand first prepared by Cram, in which two 1,1'-binaphthol system are linked through the oxygen atoms at the 2,2'-positions to form a 22-membered ring system containing six ether oxygen atoms attached to each other by four ethylene units. This was selectively mono-alkenylated to form an undec-10-en-1-yl derivative, which was bonded to linear siloxanes [HSiMe2O(SiMe2O)nSiMe2H] and [Me3SiO(Me2SiO)x(MeHSiO)ySiMe3] with total chain lengths of ca 4 and 200 Si atoms respectively, via a Pt catalysed hydrosilylation reaction.
• A simple synthetic approach to homochiral 6- and 6′-substituted 1,1′-binaphthyl derivatives
  作者：Heiko Hocke、Yasuhiro Uozumi

  DOI：10.1016/s0040-4020(02)01584-3

  日期：2003.1

  Various homochiral binaphthyl derivatives having functional groups at the 6-position are important key intermediates for the immobilization of binaphthyl compounds on various solid-supports and have been prepared from commercially available 1,1'-bi-2-naphthol via controlled monopivalation of the 2-hydroxyl group and electrophilic aromatic substitution at the 6-position. (S)-2,2'-Bis-((S)-4-alkyloxazol-2-yl)-6-(2-methoxycarbonyl)ethyl-1,1'-binaphthyls (6-functionalized (S,S)-boxax)) were prepared and immobilized on various polymer supports including PS-PEG, PS, PEGA and MeO-PEG resin. (C) 2003 Elsevier Science Ltd. All rights reserved.