(+/-)-8-amino-2'-hydroxy-1,1'-binaphthyl | 503818-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-8-amino-2'-hydroxy-1,1'-binaphthyl
• 英文别名: Iso nobin；1-(8-aminonaphthalen-1-yl)naphthalen-2-ol
• CAS: 503818-07-3；504406-37-5；504406-39-7
• 化学式: C₂₀H₁₅NO
• 分子量: 285.345
• InChiKey: GJQFDXAGSRKUPO-UHFFFAOYSA-N

物化性质

• 沸点：
  490.6±35.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (+/-)-8-amino-2'-hydroxy-1,1'-binaphthyl 在 吡啶 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (+/-)-8-acetamido-2'-hydroxy-1,1'-binaphthyl
  参考文献：
  名称：

  2,8′-Disubstituted-1,1′-Binaphthyls: A New Pattern in Chiral Ligands

  摘要：

  The title binaphthyls 19 and 26, which are the positional isomers of 2-methoxy-2'-(diphenylphosphino)-1,1'-binaphthyl (MOP, 19) and 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN, 26), have been synthesized by Suzuki coupling as the key step (10 + 15 --> 18), followed by functional group transformations, involving C-P and C-N bond formation (18 --> 19 and 18 --> 23). Racemic intermediate 22 was resolved by co-crystallization with N-benzylcinchonidinium chloride and the absolute configuration determined by X-ray crystallography. These novel binaphthyls are configurationally stable and, as such, potentially usable as chiral ligands in asymmetric reactions. Michael addition of the glycine-derived enolate 40 to methyl acrylate, carried out in the presence of (R)-(-)-27 as the chiral phase-transfer catalyst, afforded L-glutamic acid (S)-(+)-43 of 92% ee (after hydrolysis of the primary product).

  DOI：

  10.1002/1521-3765(20021018)8:20<4633::aid-chem4633>3.0.co;2-n
• 作为产物：
  描述：

  1,8-二氨基萘 在 四(三苯基膦)钯 、 [Pd(dibenzylideneacetone)2] 盐酸 、 硫酸 、 三溴化硼 、 sodium carbonate 、 溶剂黄146 、 双(2-二苯基磷苯基)醚 、 sodium t-butanolate 、 sodium nitrite 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 66.5h， 生成 (+/-)-8-amino-2'-hydroxy-1,1'-binaphthyl
  参考文献：
  名称：

  2,8′-Disubstituted-1,1′-Binaphthyls: A New Pattern in Chiral Ligands

  摘要：

  The title binaphthyls 19 and 26, which are the positional isomers of 2-methoxy-2'-(diphenylphosphino)-1,1'-binaphthyl (MOP, 19) and 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN, 26), have been synthesized by Suzuki coupling as the key step (10 + 15 --> 18), followed by functional group transformations, involving C-P and C-N bond formation (18 --> 19 and 18 --> 23). Racemic intermediate 22 was resolved by co-crystallization with N-benzylcinchonidinium chloride and the absolute configuration determined by X-ray crystallography. These novel binaphthyls are configurationally stable and, as such, potentially usable as chiral ligands in asymmetric reactions. Michael addition of the glycine-derived enolate 40 to methyl acrylate, carried out in the presence of (R)-(-)-27 as the chiral phase-transfer catalyst, afforded L-glutamic acid (S)-(+)-43 of 92% ee (after hydrolysis of the primary product).

  DOI：

  10.1002/1521-3765(20021018)8:20<4633::aid-chem4633>3.0.co;2-n

文献信息

• Synthesis of α-Amino Acids via Asymmetric Phase Transfer-Catalyzed Alkylation of Achiral Nickel(II) Complexes of Glycine-Derived Schiff Bases
  作者：Yuri N. Belokon、Natalia B. Bespalova、Tatiana D. Churkina、Ivana Císařová、Marina G. Ezernitskaya、Syuzanna R. Harutyunyan、Radim Hrdina、Henri B. Kagan、Pavel Kočovský、Konstantin A. Kochetkov、Oleg V. Larionov、Konstantin A. Lyssenko、Michael North、Miroslav Polášek、Alexander S. Peregudov、Vladimir V. Prisyazhnyuk、Štěpán Vyskočil

  DOI：10.1021/ja035465e

  日期：2003.10.1

  halides, carried out under the PTC conditions in the presence of 10% mol of (S)- or (R)-2-hydroxy-2'-amino-1,1'-binaphthyl 31a (NOBIN) and/or its N-acyl derivatives and by (S)- or (R)-2-hydroxy-8'-amino-1,1'-binaphthyl 32a (iso-NOBIN) and its N-acyl derivatives, respectively, gave rise to alpha-amino acids with high enantioselectivities (90-98.5% ee) in good-to-excellent chemical yields at room temperature

  非手性、抗磁性 Ni(II) 配合物 1 和 3 由 Ni(II) 盐和席夫碱合成，分别由甘氨酸和 PBP (7) 和 PBA (11) 在 MeONa/MeOH 溶液中生成。必要的羰基衍生剂吡啶-2-羧酸（2-苯甲酰基-苯基）-酰胺 7（PBP）和吡啶-2-羧酸（2-甲酰基-苯基）-酰胺 11（PBA）很容易从吡啶甲酸中制备。酸和邻氨基二苯甲酮或吡啶甲酸和邻氨基苯甲酸甲酯，分别。1 的结构是通过 X 射线晶体学确定的。发现配合物 1 和 3 在 PTC 条件下，在 β-萘酚或苄基三乙基溴化铵作为催化剂存在下，与卤代烷进行 C-烷基化，分别得到单-和双-烷基化产物。在温和条件下用 HCl 水溶液分解复合物，得到所需的氨基酸，并回收 PBP 和 PBA。在 PTC 条件下，在 10% mol (S)-或 (R)-2-hydroxy-2'-amino-1,1'-binaphthyl 31a (NOBIN
• 2,8′-Disubstituted-1,1′-Binaphthyls: A New Pattern in Chiral Ligands
  作者：Štěpán Vyskočil、Luděk Meca、Iva Tišlerová、Ivana Císařová、Miroslav Polášek、Syuzanna R. Harutyunyan、Yuri N. Belokon、Russel M. J. Stead、Louis Farrugia、Stephen C. Lockhart、William L. Mitchell、Pavel Kočovský

  DOI：10.1002/1521-3765(20021018)8:20<4633::aid-chem4633>3.0.co;2-n

  日期：2002.10.18

  The title binaphthyls 19 and 26, which are the positional isomers of 2-methoxy-2'-(diphenylphosphino)-1,1'-binaphthyl (MOP, 19) and 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN, 26), have been synthesized by Suzuki coupling as the key step (10 + 15 --> 18), followed by functional group transformations, involving C-P and C-N bond formation (18 --> 19 and 18 --> 23). Racemic intermediate 22 was resolved by co-crystallization with N-benzylcinchonidinium chloride and the absolute configuration determined by X-ray crystallography. These novel binaphthyls are configurationally stable and, as such, potentially usable as chiral ligands in asymmetric reactions. Michael addition of the glycine-derived enolate 40 to methyl acrylate, carried out in the presence of (R)-(-)-27 as the chiral phase-transfer catalyst, afforded L-glutamic acid (S)-(+)-43 of 92% ee (after hydrolysis of the primary product).