(S)-(-)-2-amino-2'-hydroxy-6,6'-dimethyl-1,1'-biphenyl

• 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: (S)-(-)-2-amino-2'-hydroxy-6,6'-dimethyl-1,1'-biphenyl
• 英文别名: (S)-2-amino-2'-hydroxy-6,6'-dimethyl-1,1'-biphenyl；2-(2-amino-6-methylphenyl)-3-methylphenol
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: IPAHFYCXPUDSOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(-)-2-amino-2'-hydroxy-6,6'-dimethyl-1,1'-biphenyl 在 (+)-10-camphorsulfonic acid 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 17.0h， 生成 (-)-(S)-2-((D)-10-camphorsulfonylamido)-2'-hydroxy-6,6'-dimethyl-1,1'-diphenyl
  参考文献：
  名称：

  Syntheses and resolutions of new chiral biphenyl backbones: 2-amino-2′-hydroxy-6,6′-dimethyl-1,1′-biphenyl and 2-amino-2′-hydroxy-4,4′,6,6′-tetramethyl-1,1′-biphenyl

  摘要：

  The new chiral backbones (R)-(+)- and S-(-)-2-amino-2'-hydroxy-6,6'-dimethyl-1,1'-biphenyl and (R)-(+)- and (S)- (-)2-amino-2'-hydroxy-4,4',6,6'-tetramethyl-1,1'-biphenyl were synthesized from o-methylaniline and 2,4-dimethyl-aniline respectively in seven steps. A new resolution method was developed to provide homochiral enantiomers (from diastereomeric salts) in reasonably high yields. The absolute configuration of the new biphenyls was confirmed by X-ray structural analysis. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00217-9
• 作为产物：
  描述：

  2-amino-2'-nitro-6,6'-dimethyl-1,1'-biphenyl 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 生成 (S)-(-)-2-amino-2'-hydroxy-6,6'-dimethyl-1,1'-biphenyl
  参考文献：
  名称：

  Syntheses and resolutions of new chiral biphenyl backbones: 2-amino-2′-hydroxy-6,6′-dimethyl-1,1′-biphenyl and 2-amino-2′-hydroxy-4,4′,6,6′-tetramethyl-1,1′-biphenyl

  摘要：

  The new chiral backbones (R)-(+)- and S-(-)-2-amino-2'-hydroxy-6,6'-dimethyl-1,1'-biphenyl and (R)-(+)- and (S)- (-)2-amino-2'-hydroxy-4,4',6,6'-tetramethyl-1,1'-biphenyl were synthesized from o-methylaniline and 2,4-dimethyl-aniline respectively in seven steps. A new resolution method was developed to provide homochiral enantiomers (from diastereomeric salts) in reasonably high yields. The absolute configuration of the new biphenyls was confirmed by X-ray structural analysis. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00217-9

文献信息

• Highly Enantioselective Conjugate Addition of Diethylzinc to Acyclic Enones with Fine-Tunable Phosphite−Pyridine Ligands
  作者：Huihui Wan、Yuanchun Hu、Yuxue Liang、Shuang Gao、Junwei Wang、Zhuo Zheng、Xinquan Hu

  DOI：10.1021/jo0345897

  日期：2003.10.1

  and (S)-2-amino-2'-hydroxy-4,4',6,6'-tetramethyl-1,1'-biphenyl was employed in Cu(I)-catalyzed conjugate addition of diethylzinc to acyclic enones. Excellent enantioselectivities (up to 98% ee) and highly catalytic activities were achieved for a variety of acyclic enones.

  由（S）-2-氨基-2'-羟基-6,6'-二甲基-1,1'-联苯和（S）-2衍生的一系列新的亚磷酸酯-吡啶微调（P，N）配体-氨基-2'-羟基-4,4'，6,6'-四甲基-1,1'-联苯用于二乙基锌与无环烯酮的Cu（I）催化共轭加成反应。各种无环烯酮均具有出色的对映选择性（高达98％ee）和高度催化活性。
• Lanthanide and group 4 metal complexes with new chiral biaryl-based NNO-donor ligands
  作者：Guofu Zi、Qiuwen Wang、Li Xiang、Haibin Song

  DOI：10.1039/b808238c

  日期：——

  A new series of lanthanide and group 4 metal complexes have been prepared from the reactions between Ln[N(SiMe(3))(2)](3) or M(NMe(2))(4) and chiral ligands, (R)-2-(pyrrol-2-ylmethyleneamino)-2'-methoxy-1,1'-binaphthyl (H), (S)-5,5',6,6',7,7',8,8'-octahydro-2-(pyrrol-2-ylmethyleneamino)-2'-methoxy-1,1'-b inaphthyl (H) and (R)-2-(pyrrol-2-ylmethyleneamino)-2'-methoxy-6,6'-dimethyl-1,1'-biphenyl (H)

  从Ln [N（SiMe（3））（2）]（3）或M（NMe（2））（4）与手性配体（R ）-2-（吡咯-2-基亚甲基氨基）-2'-甲氧基-1,1'-联萘基（H），（S）-5,5'，6,6'，7,7'，8,8' -八氢-2-（吡咯-2-基亚甲基氨基）-2'-甲氧基-1,1'-b萘基（H）和（R）-2-（吡咯-2-基亚甲基氨基）-2'-甲氧基-6， 6'-二甲基-1,1'-联苯（H）。配体的空间效应以及离子的尺寸效应在镧系元素络合物的形成中起着重要作用。例如，用1当量的Ln [N（SiMe（3））（2）]（3）（Ln = Y，Yb）在甲苯中处理H得到三-连接的配合物（）（3）YC（7 ）H（8）（.C（7）H（8））和（）（3）Yb.2C（7）H（8）（.2C（7）H（8））且收率高；H与1当量Sm [N（SiMe（3））（2）]（3）的反应也产生了tris连接产物（）（3）Sm（），而H与1当量Ln
• Synthesis, structure, and catalytic activity of binuclear aluminum complexes with chiral biaryl-based N2O ligands
  作者：Ning Zhao、Qiuwen Wang、Guohua Hou、Haibin Song、Guofu Zi

  DOI：10.1016/j.jorganchem.2013.12.035

  日期：2014.3

  spectroscopic techniques, elemental analyses, and X-ray diffraction analyses. Complex 7 derived from 1H2, has a C2v quasi-symmetric N4AlO2AlMe2 core structure, while complexes 8 and 10 derived from 2H2 or 4H2, adopt a C2 quasi-symmetric MeN2AlO2AlN2Me core structure, indicating that the steric effect of the ligand plays an important role in the complex formation. Complexes 7–12 are active catalysts for the

  六个新的双核有机铝配合物（1）2 Al 2 Me 2（7），（2）AlMe} 2（8），（3）AlMe} 2（9），（4）AlMe} 2（10）， （5）AlMe} 2（11）和（6）AlMe} 2（12）是通过从AlMe 3和基于手性联芳基的N 2 O配体中消除烷烃而以高收率制备的（p）-2-（吡咯-2-亚甲基氨基）-2'-羟基-1,1'-联萘基（1 H 2），（S）-5,5'，6,6'，7,7'，8， 8'-八氢-2-（吡咯-2-亚甲基氨基）-2'-羟基-1,1'-联萘基（2 H 2），（S）-2-（吡咯-2-亚甲基氨基）-2'-羟基-6,6'-二甲基-1,1'-联苯（3 H 2），（S）-2-（吡啶-2-基甲基氨基）-2'-羟基-1,1'-联萘基（4 H 2） ，（S）-5,5'，6,6'，7,7'，8,8'-八氢-2-（吡啶-2-基甲基氨基）-2'-羟基-1,1'-联萘基（5
• Development of new chiral P,N ligands and their applications in enantioselective 1,4-conjugate additions of diethylzinc to chalcones
  作者：Yuxue Liang、Shuang Gao、Huihui Wan、Yuanchun Hu、Huilin Chen、Zhuo Zheng、Xinquan Hu

  DOI：10.1016/j.tetasy.2003.09.001

  日期：2003.10

  Examples of a new type of chiral phosphine-pyridine ligand have been synthesized from (R)-2-amino-2'-hydroxy-6,6'-dimethyl-1.1'-biphenyl and (R)-2-amino-2'-hydroxy-4,4',6,6'-tetramethyl-l,l'-biphenyl in six steps and successfully employed in Cu(I)-catalysed conjugate additions of diethylzine to chalcones. Up to 96.1% ee and high activities were achieved. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis, structure, and catalytic activity of organoaluminum complexes with chiral biaryl Schiff-base ligands
  作者：Ning Zhao、Qiuwen Wang、Guohua Hou、Haibin Song、Guofu Zi

  DOI：10.1016/j.ica.2014.01.009

  日期：2014.3

  A new series of organoaluminum complexes have been prepared by alkane elimination in good yields from AlMe3 and chiral biaryl Schiff-base NO2 ligands, 1H(2)-7H(2), which are derived from (S)-2-amino-2 ' hydroxy-1,1 '-binaphthyl or (S)-2-amino-2 '-hydroxy-6,6 '-dimethyl-1,1 '-biphenyl, respectively. However, solvent plays an important role in the formation of the aluminum complexes. For example, treatment of ligand 1H(2) with 1 equiv of AlMe3 in THF gives the mononuclear complex (1)AlMe(THF) (8) in 90% yield. While reaction of 2H(2), 3H(2), 4H(2), 5H(2), 6H(2) or 7H(2) with 1 equiv of AlMe3 in benzene gives the binuclear complexes (2)AlMe}(2) (9), (3)AlMe}(2) (10), (4)AlMe}(2) (11), (5)AlMe}(2) (12), (6)AlMe}(2) (13) and (7)AlMe}(2) (14), respectively, in good yields. Complexes 8-14 have been characterized by various spectroscopic techniques, elemental analyses, and X-ray diffraction analyses. The complexes 8-14 are active catalysts for the polymerization of rac-lactide in the presence of isopropanol, leading to the heterotacticrich polylactides. (C) 2014 Elsevier B.V. All rights reserved.