2-hydroxy-2'-nitro-6,6'-dimethyl-1,1'-biphenyl | 57568-91-9

• 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: 2-hydroxy-2'-nitro-6,6'-dimethyl-1,1'-biphenyl
• 英文别名: 3-methyl-2-(2-methyl-6-nitrophenyl)phenol
• CAS: 57568-91-9；58960-58-0
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: OLCPCTLUTKKMFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  63.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-2'-nitro-6,6'-dimethyl-1,1'-biphenyl 在 palladium on activated charcoal 氢气 、 (+)-10-camphorsulfonic acid 、 三乙胺 作用下， 以 乙醇 、 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 盐酸 、 sodium nitrite 、 硫酸 作用下， 以 乙醇 、 甲苯 为溶剂， 以60%的产率得到2-hydroxy-2'-nitro-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

• Racemization Catalyst for Amino Acid. IV Enantiomer Differentiating Racemization with (<i>S</i>)-2′-Nitro-5-nitroso-6,6′-dimethylbiphenyl-2-ol
  作者：Kazuhiro Hirota

  DOI：10.1246/bcsj.48.2509

  日期：1975.9

  racemizations of both enantiomers of alanine were carried out with (S)-2′-nitro-5-nitroso-6,6′-dimethylbiphenyl-2-ol (1) in the presence of cupric ion. In time course studies, the apparent half-life of D-alanine is longer than that of L-alanine. Such an enantiomer differentiating ability is explained by a mechanism involving a reactive product formed from the preferred conformation of the diastereomeric

  在铜离子的存在下，丙氨酸的两种对映异构体的外消旋化是用 (S)-2'-nitro-5-nitroso-6,6'-二甲基联苯-2-ol (1) 进行的。在时间进程研究中，D-丙氨酸的表观半衰期长于 L-丙氨酸。这种对映异构体的区分能力可以通过一种机制来解释，该机制涉及由非对映体铜配合物的优选构象形成的反应产物，分别由 1 和 D-或 L-丙氨酸组成。还介绍了通过拆分 2'-硝基-6,6'-二甲基联苯-2-胺合成 1。