(S)-o-(1-phenylethylaminomethyl)phenol | 77382-97-9

• 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: (S)-o-(1-phenylethylaminomethyl)phenol
• 英文别名: N-(2-hydroxybenzyl)-(S)-α-methylbenzylamine；(S)-(+)-N-(1-phenylethyl) salicylideneamine；2-[[[(1S)-1-phenylethyl]amino]methyl]phenol
• CAS: 77382-97-9
• 化学式: C₁₅H₁₇NO
• mdl: MFCD24870932
• 分子量: 227.306
• InChiKey: BYIZBEHMSPRAPK-LBPRGKRZSA-N

物化性质

• 沸点：
  354.7±22.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-o-(1-phenylethylaminomethyl)phenol 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 N-(2-hydroxybenzyl)-N-((S)-1-phenylethyl)phenylsulfinamide
  参考文献：
  名称：

  Hiroi, Kunio; Sato, Shuko; Kitayama, Ryuichi, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 10, p. 3471 - 3485

  摘要：

  DOI：
• 作为产物：
  描述：

  2-N-((S)-1-phenylethyl)salicylaldimine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (S)-o-(1-phenylethylaminomethyl)phenol
  参考文献：
  名称：

  Synthesis of Chiral 1,4,2-Oxazaphosphepines

  摘要：

  本文描述了1,4,2-氧杂磷氮杂环己二烯的合成及其结构表征。这些化合物是通过手性的1,3-苯并噁嗪与二氯苯基膦或三乙基磷酸酯反应得到的。其中一些化合物的构型是通过X射线分析确定的。

  DOI：

  10.3390/molecules200813794

文献信息

• Dicopper(II) Complexes with the Enantiomers of a Bidentate Chiral Reduced Schiff Base: Inclusion of Chlorinated Solvents and Chiral Recognition of1,2‐Dichloroethane Rotamers in the Crystal Lattice
  作者：Vamsee Krishna Muppidi、Samudranil Pal

  DOI：10.1002/ejic.200600248

  日期：2006.7

  groups. 1·CH 2 Cl 2 and 2·CH 2 Cl 2 crystallise in the P2 1 space group while 1·CHCl 3 , 2·CHCl 3 , 1·Cl(CH 2 ) 2 Cl and 2·Cl(CH 2 ) 2 Cl crystallise in the P2 1 2 1 2 1 space group. In these inclusion crystals, the C-H···Cl interactions between the guest and the host molecules are primarily responsible for enclatheration of the chloroalkane molecules. In the case of CH 2 Cl 2 , one of its Cl atoms acts

  Bisphenoxo-bridged dicopper(II) 配合物 [Cu 2 L n 2 Cl 2 ] 1 (n = 1) 和 2 (n = 2)} 与 N,O-供体还原的席夫碱 N-(2-羟基苄基)- (R)-α-甲基苄胺(HL 1 )和N-(2-羟基苄基)-(S)-α-甲基苄胺(HL 2 )已被合成和表征。在 1 和 2 中，双齿手性配体通过仲胺 N 原子和桥接酚盐 O 原子与金属中心配位。氯离子占据第四个配位点，并在每个铜 (II) 中心周围完成一个略微扭曲的方形平面 NO 2 Cl 环境。固态磁化率测量表明两种配合物中金属中心之间存在强烈的反铁磁相互作用。1 和 2 都容易与氯化溶剂如 CH 2 Cl 2 、CHCl 3 和 Cl(CH 2 ) 2 Cl 形成 1:1 的主客体化合物。所有的主客体化合物都在非中心对称空间群中结晶。1·CH 2 Cl 2 和2·CH 2 Cl
• Generation of chiral bis(cyclopentadienyl)neodymium Schiff base complex bearing internal C-C bond formation and hydrogen transfer
  作者：Qiancai Liu、Mengxian Ding、Yonghua Lin、Yan Xing

  DOI：10.1016/s0022-328x(97)00463-4

  日期：1997.12

  NdCl3 reacts with excess CpNa (Cp=Cyclopentadienyl) in THF, followed by sequent treatment with (S)-(+)-N-(1-phenylethyl)salicylideneamine led to the formation of title compound, . The X-ray structure determination shows that it is a dimer with internal C-C bond formation and hydrogen transfer between one of Cp ring and the C=N bond of Schiff base ligand.

  NdCl 3与过量的CpNa（Cp =环戊二烯基）在THF中反应，然后依次用（S）-（+）- N-（1-苯乙基）水杨亚胺处理，形成标题化合物。X射线结构测定表明，它是具有内部CC键形成且Cp环之一与席夫碱配体的C ＝ N键之间的氢转移的二聚体。
• Synthesis and crystal structure of chiral bis(cyclopentadienyl) samarium Schiff base complexes bearing intramolecular CC bond formation and hydrogen transfer
  作者：Qiancai Liu、Mengxian Ding、Yonghua Lin、Yan Xing

  DOI：10.1016/s0277-5387(97)00511-1

  日期：1998.1

  Abstract SmCl3 reacted with CpNa (Cp = Cyclopentadienyl) in the ratio of 1 : 3 in THF, which then was reacted with (S)−(+)-N-1-(phenylethyl)salicylideneamine/toluene to yield the title complex, The X-ray crystal structure determination of the title complex reveals that 1 is a dimer with intramolecular CC bond formation and hydrogen transfer, which leads to the configuration turnover of the carbon

  摘要SmCl3与CpNa（Cp =环戊二烯基）在THF中以1：3的比例反应，然后与（S）-（+）-N-1-（苯乙基）水杨亚胺/甲苯反应生成标题化合物，标题配合物的X射线晶体结构测定表明，1是具有分子内CC键形成和氢转移的二聚体，这导致配体苄基位置的碳原子的构型转换，而新分子则为碳原子的构型转换。形成的不对称中心可以具有R型或S型配置。
• Asymmetric synthesis of new chiral long chain alcohols
  作者：Tülay Yıldız、Ayşe Yusufoğlu

  DOI：10.1016/j.tetasy.2010.12.010

  日期：2010.12

  Sixteen new chiral alcohols with alkyl (C-11-C-19) and aryl, substituted aryl, hetero aryl and biaryl groups 2a-2t were synthesized by three different asymmetric reduction methods from their corresponding ketones 1a-1t. Chiral NaBH4 (method A), chiral BH3 (method B) and chiral AIP (method C) were used as asymmetric reduction catalysts. Chiral NaBH4 was modified by four different ligands 3a-3d, chiral BH3 and chiral AIP by four different ligands 4a-4d. Ligand 4c was synthesized for the first time in this work. Chiral NaBH4 generated chiral alcohols of (R)-configuration and chiral BH3 and chiral AIP of (S)-configuration with high enantiomeric excesses, were analysed by chiral HPLC. In order to determine the ee values by chiral HPLC, sixteen corresponding racemic alcohols, synthesized by reducing their corresponding ketones via NaBH4, were used for chiral resolution on a Daicel OD HPLC column. The sixteen starting ketones were synthesized in this study by Friedel-Craft acylation. The new chiral alcohols were characterized by IR, NMR, (H-1 and C-13), MS, elemental analyses and specific rotation. The reduction methods A, B and C were applied to these ketones for the first time in this study and were compared with each other. The relationship between the structure of the ketone and the yield and the enantiomeric excess was discussed. (C) 2010 Elsevier Ltd. All rights reserved.
• Enantioselective cyclopropanation of 1,1-diphenylethylene and diazoacetic acid ester with copper catalysts
  作者：Henri Brunner、Wolfgang Miehling

  DOI：10.1007/bf00809355

  日期：1984.10