(2S)-2-[(2-羟基苯基)甲基氨基]-4-甲基戊酸 | 175029-33-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (2S)-2-[(2-羟基苯基)甲基氨基]-4-甲基戊酸
• 中文别名: L-亮氨酸,N-[(2-羟基苯基)甲基]-
• 英文名称: N-(2-hydroxybenzyl)-L-leucine
• 英文别名: (S)-2-(2-hydroxybenzylamino)-4-methylpentanoic acid；(2S)-2-[(2-hydroxyphenyl)methylamino]-4-methylpentanoic acid
• CAS: 175029-33-1
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: CKOZCUWWRVLXLB-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(2-羟基苯基)甲基氨基]-4-甲基戊酸 、 苯硼酸 以 二甲基亚砜 、 苯 为溶剂， 以97%的产率得到(2S,5S,6R)-2-phenyl-6-aza-1,3-dioxa-5-isobutyl-2-borabenzocyclononen-4-one
  参考文献：
  名称：

  X-ray analysis and structural characterization of 2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononenones

  摘要：

  Nine new monomeric boronates of the type 2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononen-4-ones (3a-3i) were prepared from N-(2-hydroxybenzyl)-alpha-aminoacids 1a-1i and phenylboronic acid 2 using 20:1 benzene-DMSO mixtures. The compounds were characterized by H-1-, C-13-, B-11-, N-15- and 2D-NMR (HETCOR, NOESY and COLOC) experiments, FT infrared, mass spectra and elemental analysis. Suitable monocrystals of cis-2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononen-4-one (3a), (2S,5S,6R)-2-phenyl-6-aza- 1,3-dioxa-5-sec butyl-2-borabenzocyclononen-4-one (3c) and 2,5-diphenyl-6-aza-1,3-dioxa-2-borabenzocyclononen-4-one (3h) were obtained and their structures are discussed. The X-ray structures, as well as the NMR data established that the configurations at the nitrogen and boron atoms are 'R' and 'S', respectively and the transannular fusion is cis. A semi-empirical (SAMI) study allowed calculation of the energy for all possible stereoisomers, showing that the stabilization increases as the THC (TetraHedral Character of the boron atom) increases and also as the N --> B bond distance decreases, in agreement with the experimental results. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(02)01418-3
• 作为产物：
  描述：

  L-C6H4(OH)CHNCH(CH2CH(CH3)2)COOH 在 sodium tetrahydroborate 作用下， 生成 (2S)-2-[(2-羟基苯基)甲基氨基]-4-甲基戊酸
  参考文献：
  名称：

  Assessing the Effect of Ligand Proximity on Chiroptical and Other Properties in Cobalt(III) Model, Tyrosine-Like Complexes

  摘要：

  一系列新的钴（III）八面体配合物的通式为Na[Co(ohb-aa)₂]（ohb-aa = N-(o-羟基苯甲基)氨基酸根离子）；氨基酸=甘氨酸，(S)-α-丙氨酸，α-氨基异丁酸，(S)-缬氨酸，(S)-正缬氨酸和( S)-亮氨酸），通过适当配体在碱性水溶液中与[Co(NH₃)₆]³⁺在木炭催化下反应制备。无论使用哪种氨基酸，所得到的配合物具有相同的facial all-trans对称性（CoN₂O₄色团），邻位效应是光学活性的全部来源。¹³C NMR光谱显示，由于立体位阻，亮氨酸衍生物具有不同的基态结构。吸收峰反映了氨基酸侧链碳原子的正电感应效应。具有亲电性烷基基团的配体配合物与甘氨酸衍生物相比，表现出更负的E_1/2，其还原发生在更正的电位。还原电位与由配体调节的钴（III）路易斯酸性不相关。

  DOI：

  10.1135/cccc19952097

文献信息

• Sodium and Potassium Ion Directed Self-Assembled Multinuclear Assembly of Divalent Nickel or Copper and <scp>l</scp>-Leucine Derived Ligand
  作者：Mrigendra Dubey、Rik Rani Koner、Manabendra Ray

  DOI：10.1021/ic9011444

  日期：2009.10.5

  supramolecular assembly with the formula [KNi(HLl-leu)2}3]+ (1). Structural characterization showed three [Ni(HLl-leu)2] units encapsulated K+ similar to organic crown ethers/cryptand. Substituting Ni(II) with Cu(II) and K+ with Na+ in the above reaction resulted in a set of structurally identical assemblies with the general formula [M′M(HLl-leu)2}3]+, where M′ is either K+ or Na+ and M is either Cu(II) or

  1-亮氨酸衍生的配体（H 2 L 1- leu），KOH和Ni（II）盐以2：2：1的比例自组装成较大的（〜13Å）超分子组装体，其分子式为[K Ni （HL 1- leu）2 } 3 ] +（1）。结构表征显示三个[Ni（HL 1 -leu）2 ]单元包封了K +，类似于有机冠醚/穴状配体。在上述反应中，用Cu（II）取代Ni（II），用Na +取代K +，得到了一组结构相同的通式[M'M（HL l-leu）2 } 3 ] +，其中M'为K +或Na +，M为Cu（II）或Ni（II）；[Na Ni（HL 1- leu）2 } 3 ] ClO 4（2），Na Ni（HL 1- leu）2 } 3 ] OTf（3），[K Cu（HL 1- leu）2 } 3 ] ClO 4（4），[Na Cu（HL 1- leu）2 } 3 ] ClO 4（5），[K Cu（HL 1- leu）2
• Highly efficient electrochemical recognition and quantification of amine enantiomers based on a guest-free homochiral MOF
  作者：Rui Kuang、Luyi Zheng、Yanhui Chi、Jingmin Shi、Xuexue Chen、Chengcheng Zhang

  DOI：10.1039/c7ra00205j

  日期：——

  A novel homochiral MOF was facilely synthesized, its nanocrystals exhibit rapid discrimination of α-methylbenzylamine enantiomers and quantitative determination of enantiomeric excess.

  一种新型的同手性金属有机框架（MOF）被轻松地合成，其纳米晶体能够快速区分α-甲基苯乙胺对映异构体并定量测定对映异构体过量。
• Assessing the Effect of Ligand Proximity on Chiroptical and Other Properties in Cobalt(III) Model, Tyrosine-Like Complexes
  作者：František Jursík、Ronald D. Archer

  DOI：10.1135/cccc19952097

  日期：——

  A series of new cobalt(III) octahedral complexes of the general formula Na[Co(ohb-aa)₂] (ohb-aa = N-(o-hydroxybenzyl)amino acid anion); amino acid = glycine, (S)-α-alanine, α-aminoisobutyric acid, (S)-valine, (S)-norvaline and (S)-leucine) were prepared by the charcoal catalyzed reaction of the appropriate ligand with [Co(NH₃)₆]³⁺ in alkaline aqueous solution. Complexes obtained have, regardless of the amino acid used, the same facial all-trans symmetry (CoN₂O₄ chromophore) with the vicinal effects as the entire source of the optical activity. ¹³C NMR spectra reveal that the leucine derivative has, due to the steric reasons, a different ground state structure. Absorption maxima reflect a positive inductive effect from the amino acid side chain carbon atoms. Complexes of the ligands bearing electrophobic alkyl groups exhibit more negative E_1/2 in comparison with the glycine derivative, reduction of which occurs at a more positive potential. Reduction potentials do not correlate with cobalt(III) Lewis acidity modulated by ligands.

  一系列新的钴（III）八面体配合物的通式为Na[Co(ohb-aa)₂]（ohb-aa = N-(o-羟基苯甲基)氨基酸根离子）；氨基酸=甘氨酸，(S)-α-丙氨酸，α-氨基异丁酸，(S)-缬氨酸，(S)-正缬氨酸和( S)-亮氨酸），通过适当配体在碱性水溶液中与[Co(NH₃)₆]³⁺在木炭催化下反应制备。无论使用哪种氨基酸，所得到的配合物具有相同的facial all-trans对称性（CoN₂O₄色团），邻位效应是光学活性的全部来源。¹³C NMR光谱显示，由于立体位阻，亮氨酸衍生物具有不同的基态结构。吸收峰反映了氨基酸侧链碳原子的正电感应效应。具有亲电性烷基基团的配体配合物与甘氨酸衍生物相比，表现出更负的E_1/2，其还原发生在更正的电位。还原电位与由配体调节的钴（III）路易斯酸性不相关。
• X-ray analysis and structural characterization of 2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononenones
  作者：Hiram I Beltrán、Luis S Zamudio-Rivera、Teresa Mancilla、Rosa Santillan、Norberto Farfán

  DOI：10.1016/s0022-328x(02)01418-3

  日期：2002.9

  Nine new monomeric boronates of the type 2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononen-4-ones (3a-3i) were prepared from N-(2-hydroxybenzyl)-alpha-aminoacids 1a-1i and phenylboronic acid 2 using 20:1 benzene-DMSO mixtures. The compounds were characterized by H-1-, C-13-, B-11-, N-15- and 2D-NMR (HETCOR, NOESY and COLOC) experiments, FT infrared, mass spectra and elemental analysis. Suitable monocrystals of cis-2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononen-4-one (3a), (2S,5S,6R)-2-phenyl-6-aza- 1,3-dioxa-5-sec butyl-2-borabenzocyclononen-4-one (3c) and 2,5-diphenyl-6-aza-1,3-dioxa-2-borabenzocyclononen-4-one (3h) were obtained and their structures are discussed. The X-ray structures, as well as the NMR data established that the configurations at the nitrogen and boron atoms are 'R' and 'S', respectively and the transannular fusion is cis. A semi-empirical (SAMI) study allowed calculation of the energy for all possible stereoisomers, showing that the stabilization increases as the THC (TetraHedral Character of the boron atom) increases and also as the N --> B bond distance decreases, in agreement with the experimental results. (C) 2002 Elsevier Science B.V. All rights reserved.