(R)-5,5'-diamino-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-5,5'-diamino-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl
• 英文别名: (R)-5,5'-diamino-2,2'-di(biphenylphosphino)-1,1'-binaphthyl；(R)-5,5'-diamino BINAP；(R)-5,5'-diamino-BINAP；1,1'-Bi[2-(diphenylphosphino)naphthalene-5-amine]；5-(5-amino-2-diphenylphosphanylnaphthalen-1-yl)-6-diphenylphosphanylnaphthalen-1-amine
• 化学式: C₄₄H₃₄N₂P₂
• 分子量: 652.715
• InChiKey: RVZRKTNERMCUSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  48
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-二羟基苯甲酸 、 (R)-5,5'-diamino-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl 在 吡啶 、 三苯基膦 、 calcium chloride 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成
  参考文献：
  名称：

  A novel system consisting of easily recyclable dendritic Ru-BINAP catalyst for asymmetric hydrogenationElectronic supplementary information (ESI) available: synthesis details, partition coefficients of dendritic BINAP ligands and their Ru complexes, hydrogenation and recycling procedure. See http://www.rsc.org/suppdata/cc/b2/b203117e/

  摘要：

  外围烷基链功能化的树枝状Ru-BINAP催化剂与添加少量水引起相分离的有机二元溶剂体系一起用于不对称氢化反应，具有高催化活性和对映选择性以及易于催化剂回收。

  DOI：

  10.1039/b203117e

文献信息

• Assembling Behavior of BINAP Derivative
  作者：Peng Wu、Guojun Deng、Qinghua Fan、Qingdao Zeng、Chen Wang、Lijun Wan、Chunli Bai

  DOI：10.1246/cl.2002.706

  日期：2002.7

  Ordered assembly of dendritic BINAP ligand has been studied by using scanning tunneling microscopy (STM). It is proposed that the molecules are arranged in a dimeric manner in the assembly.

  使用扫描隧道显微镜 (STM) 研究了树状 BINAP 配体的有序组装。建议分子在装配体中以二聚体方式排列。
• Highly effective and recyclable dendritic BINAP ligands for asymmetric hydrogenation
  作者：Qing-Hua Fan、Yong-Ming Chen、Xiao-Min Chen、Da-Zhi Jiang、Fu Xi、Albert S. C. Chan

  DOI：10.1039/b001503m

  日期：——

  A series of dendritic BINAP ligands have been synthesised and their ruthenium complexes used as catalysts in asymmetric hydrogenation.

  已经合成了一系列树枝状 BINAP 配体，并将它们的钌配合物用作不对称氢化的催化剂。
• Phosphine compounds for complex catalysts for asymmetric syntheses
  申请人：Takasago Perfumery Co., Ltd.

  公开号：EP0235450A1

  公开（公告）日：1987-09-09

  A phosphine compound is represented by formula: wherein R represents a hydrogen atom or an acetyl group; and Ph represents a phenyl group. Synthesis is from BINAP dioxide by nitration at the 5,5 positions, conversion of the nitro groups to amino groups by reduction, e.g. with SnCl₂, reduction of the carbon with H Si Cl₃ and optional acetylation of the -NH₂ groups. The compound is reacted with a compound of rhodium, ruthenium or palladium [Rh(nobornadiene)₂] ClO₄, to form a metal complex.

  膦化合物由式表示：其中 R 代表氢原子或乙酰基；Ph 代表苯基。 合成方法是以二氧化 BINAP 为原料，在 5,5 位上进行硝化，通过还原（例如用 SnCl₂）将硝基转化为氨基，用 H Si Cl₃还原碳，然后任选对-NH₂基团进行乙酰化。 该化合物与铑、钌或钯的化合物[Rh(nobornadiene)₂] ClO₄反应，形成金属配合物。
• Catalytic production of optically active carboxylic acid
  申请人：Takasago International Corporation

  公开号：EP0272787A2

  公开（公告）日：1988-06-29

  A carboxylic acid having optically active C atom, of formula: wherein R1, R2 and R3 each represents hydrogen, alkyl, alkenyl, or phenyl or naphthyl which may have a substituent, provided that all of R1 to R3 are not simultaneously hydrogen; when R1 and R2 are both hydrogen then R3 is not methyl and when R3 is hydrogen, R1 and R2 are each other than hydrogen, is produced by dissolving an a,β-unsaturated carboxylic acid represented by the formula: in an aprotic solvent, optionally adding equimolar tertiary amine and adding a ruthenium-optically active phosphine complex as a catalyst, hydrogenating under pressure of 4-135 kg/cm2, and distilling off the solvent. Three classes of such catalyst, containing a 'BINAP' group, are shown, and syntheses thereof. The carboxylic acids produced can be used as raw materials for syntheses, e.g. of physiologically active substances of natural materials, and also as liquid crystal materials.

  具有光学活性 C 原子的羧酸，其式如下 式中 R1、R2 和 R3 分别代表氢、烷基、烯基或苯基或萘基，它们可以有一个取代基，但 R1 至 R3 不能同时为氢；当 R1 和 R2 都为氢时，R3 不是甲基，当 R3 为氢时，R1 和 R2 不是氢： 将 a，β-不饱和羧酸溶解于非烷基溶剂中，选择性地加入等摩尔叔胺，并加入钌-光活性膦络合物作为催化剂，在 4-135 kg/cm2 的压力下进行氢化，然后蒸馏掉溶剂。 图中展示了三类含有 "BINAP "基团的催化剂及其合成方法。 生成的羧酸可用作合成原料，如天然材料中的生理活性物质，也可用作液晶材料。
• Process for the preparation of non-chiral and optically active organic compounds containing hydroxyl groups
  申请人：——

  公开号：US20020111515A1

  公开（公告）日：2002-08-15

  Non-chiral and, in particular, optically active alcohols are prepared from a carbonyl compound with hydrogen in the presence of a catalyst, a base and optionally a diamine in an advantageous manner if a catalyst it used which contains both a support-bonded Ru(II) complex bisphosphine liquid and also a diamine ligand.

  在催化剂、碱和二胺存在的情况下，用羰基化合物加氢制备非手性，特别是光学活性醇，如果使用的催化剂既含有支撑键合的 Ru(II) 复合物双膦液，又含有二胺配体，则制备方法更为有利。