tert-butyl N-[(1S)-1-({[(1S)-2-hydroxy-1-phenylethyl]amino}carbonyl)-2-methylpropyl]carbamate | 496838-62-1

• 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
• 英文名称: tert-butyl N-[(1S)-1-({[(1S)-2-hydroxy-1-phenylethyl]amino}carbonyl)-2-methylpropyl]carbamate
• 英文别名: tert-butyl ((S)-1-(((S)-2-hydroxy-1-phenylethyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate；tert-butyl 1-(2-hydroxy-1-phenylethylamino)-3-methyl-1-oxobutan-2-yl carbamate；tert-butyl N-[(2S)-1-[[(1S)-2-hydroxy-1-phenylethyl]amino]-3-methyl-1-oxobutan-2-yl]carbamate
• CAS: 496838-62-1
• 化学式: C₁₈H₂₈N₂O₄
• 分子量: 336.431
• InChiKey: HPWMDECGGBAKGS-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S)-1-({[(1S)-2-hydroxy-1-phenylethyl]amino}carbonyl)-2-methylpropyl]carbamate 在 盐酸 、 氯化亚砜 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 以43%的产率得到(S)-2-Amino-N-((S)-2-chloro-1-phenyl-ethyl)-3-methyl-butyramide
  参考文献：
  名称：

  新型高度模块化的C 2对称的恶唑啉配体－在钛催化的乙二醛锌加成中的应用

  摘要：

  从α-氨基酸，1,2-氨基醇和1,2-或1,3-二酸有效地制备了新型的C 2对称四齿双恶唑啉配体。将配体用于钛催化的二乙基锌与苯甲醛的加成反应中，并根据所用条件，获得所形成的1-苯基丙醇的中等至高对映选择性。

  DOI：

  10.1016/s0040-4039(02)00087-4
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium hydroxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 tert-butyl N-[(1S)-1-({[(1S)-2-hydroxy-1-phenylethyl]amino}carbonyl)-2-methylpropyl]carbamate
  参考文献：
  名称：

  新型高度模块化的C 2对称的恶唑啉配体－在钛催化的乙二醛锌加成中的应用

  摘要：

  从α-氨基酸，1,2-氨基醇和1,2-或1,3-二酸有效地制备了新型的C 2对称四齿双恶唑啉配体。将配体用于钛催化的二乙基锌与苯甲醛的加成反应中，并根据所用条件，获得所形成的1-苯基丙醇的中等至高对映选择性。

  DOI：

  10.1016/s0040-4039(02)00087-4

文献信息

• Rhodium-Catalyzed Asymmetric Transfer Hydrogenation of Aryl Alkyl Ketones Employing Ligands Derived from Amino Acids
  作者：Jenny Wettergren、Alexey B. Zaitsev、Hans Adolfsson

  DOI：10.1002/adsc.200700345

  日期：2007.12.10

  The combination of (pentamethylcyclopentadienyl)rhodium dichloride dimer [RhCl2Cp*}2] and pseudodipeptide ligands, formed from N-Boc protected amino acids and amino alcohols, resulted in efficient and selective catalysts for the asymmetric transfer hydrogenation of ketones in 2-propanol. A number of different secondary alcohols was obtained in high yields and in excellent enantioselectivity using

  （五甲基环戊二烯基）二氯化铑二聚体[RhCl 2 Cp *} 2 ]和由N- Boc保护的氨基酸和氨基醇形成的假二肽配体的组合，导致了高效且选择性的催化剂，用于2-酮的不对称转移加氢丙醇。使用这些原位形成的催化剂，以高收率和优异的对映选择性获得了许多不同的仲醇。氘标记实验表明，氢化物转移反应是通过单氢途径发生的。
• Direct Asymmetric syn-Aldol Reactions of Linear Aliphatic Ketones with Primary Amino Acid-Derived Diamines
  作者：Anneleen L. W. Demuynck、Jozef Vanderleyden、Bert F. Sels

  DOI：10.1002/adsc.201000419

  日期：2010.10.4

  novel class of chiral diamine organocatalysts based on natural primary amino acids that efficiently catalyze syn-selective aldol reactions of challenging linear ketones, such as 2-butanone, and aromatic aldehydes. In the presence of trifluoroacetic acid (TFA) as Brønsted acid and 2,4-dinitrophenol (DNP) as co-catalyst, syn-aldol products have been obtained with excellent enantioselectivities of up to> 99%

  我们基于天然伯氨基酸设计了新颖的一类手性二胺有机催化剂，其有效催化具有挑战性的线性酮如2-丁酮和芳族醛的顺式-选择性羟醛反应。在三氟乙酸（TFA）作为布朗斯台德酸和2,4-二硝基苯酚（DNP）作为助催化剂的存在下，已获得具有高达> 99％ee的优异对映选择性的顺式醛醇产物。
• Synthesis of the Nonribosomal Peptide Phevalin and Analogs
  作者：Remya Ramesh、Michael T. Bovino、Yibin Zeng、Jeffrey Aubé

  DOI：10.1021/acs.joc.8b03206

  日期：2019.3.15

  Phevalin, a cyclic nonribosomal peptide produced by Staphylococcus aureus, has intriguing biological properties. A synthetic route to access phevalin and similar pyrazinone natural products tyrvalin, leuvalin, phileucin, and a few synthetic analogs is described. The reaction sequence involves a one-pot carbamate deprotection/imine formation/aerobic oxidation to form the pyrazinone-containing products

  Phevalin是一种由金黄色葡萄球菌产生的环状非核糖体肽，具有令人着迷的生物学特性。描述了一种获取麻黄素和类似吡嗪酮天然产物酪氨酸，酪氨酸，phileucin和一些合成类似物的合成途径。反应顺序涉及一锅氨基甲酸酯脱保护/亚胺形成/好氧氧化以形成含吡嗪酮的产物。
• Synthesis, characterization and in vitro DNA binding studies of tin(IV) complexes of tert-butyl 1-(2-hydroxy-1-phenylethylamino)-3-methyl-1-oxobutan-2-yl carbamate
  作者：Farukh Arjmand、Jamsheera A.

  DOI：10.1016/j.jorganchem.2011.08.009

  日期：2011.11

  Tin(IV) complexes 1(a and b) and 2(a and b) of valine derived peptide derivatives were synthesized and characterized on the basis of elemental analysis, IR, (1) H, C-13, Sn-119 NMR, ESI-MS spectra and molar conductance measurements. The C-Sn-C angle was estimated from C-I3 and H-1 NMR data (1)J(Sn-119, C-I3) = 623 Hz; solution (2)J(Sn-119, H-1) = 93.04 Hz to be 149.9 degrees. In vitro binding studies of complexes 1 and 2 under physiological conditions at room temperature with CT-DNA were carried out employing UV-visible, fluorescence, circular dichroism and viscometric studies. The binding affinity of the complexes was quantified by calculating the K-b values and it follows the order 2a > 1a > 2b > 1b. To further examine the specific mode of binding, the interaction of complexes 2(a and b) were carried out with 5'GMP and 5'TMP by using absorption and NMR (H-1, P-31) spectroscopy. The supercoiled pBR322 plasmid DNA cleavage activity of the complexes was ascertained by gel electrophoresis assay. The complexes cleave supercoiled pBR322 plasmid DNA efficiently into its nicked form at micromolar concentrations. (C) 2011 Elsevier B. V. All rights reserved.
• Employing the Structural Diversity of Nature: Development of Modular Dipeptide-Analogue Ligands for Ruthenium-Catalyzed Enantioselective Transfer Hydrogenation of Ketones
  作者：Isidro M. Pastor、Patrik Västilä、Hans Adolfsson

  DOI：10.1002/chem.200304900

  日期：2003.9.5

  stereocenters, it was demonstrated that the absolute configuration of the product alcohol was determined by the configuration of the amino acid part of the ligand. Employing ligands based on L-amino acids generated S-configured products, and catalysts based on D-amino acids favored the formation of the R-configured alcohol. The combination N-Boc-L-alanine and (R)-phenylglycinol (Boc-L-Ab) or its enantiomer

  基于叔丁氧羰基（N-Boc）-保护的α-氨基酸和手性邻位氨基醇的组合，制备了新颖的二肽-类似物配体的文库。这些高度模块化的配体与[[RuCl（2）（p-cymene）]（2）]结合，并筛选得到的金属配合物作为催化剂，用于在转移氢化条件下使用2-丙醇作为氢供体的对苯乙酮对映选择性还原。用几种新颖的催化剂可获得极好的1-苯基乙醇对映体选择性（ee高达98％）。尽管大多数配体包含两个立体中心，但已证明产物醇的绝对构型是由配体的氨基酸部分的构型决定的。利用基于L-氨基酸的配体生成S-构型产物，基于D-氨基酸的催化剂有利于R-构型醇的形成。N-Boc-L-丙氨酸和（R）-苯基甘醇（Boc-L-Ab）或其对映异构体（N-Boc-D-丙氨酸和（S）-苯基甘醇，Boc-D-Aa）的组合被证明是还原过程的最佳配体。评估了许多芳基烷基酮的转移氢化反应，并获得了极佳的对映选择性，最高可达96％ee。