N-(R)-1-(1-naphthyl)ethyl methyl carbamate | 71872-01-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(R)-1-(1-naphthyl)ethyl methyl carbamate
• 英文别名: (R)-(+)-N-methoxycarbonyl-1-(1-naphthyl)ethylamine；methyl N-[(1R)-1-naphthalen-1-ylethyl]carbamate
• CAS: 71872-01-0
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: JEHSZZXIWRHTSJ-SNVBAGLBSA-N

物化性质

• 沸点：
  393.1±21.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(R)-1-(1-naphthyl)ethyl methyl carbamate 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-bromo-N-methyl-N-[(1R)-1-naphthalen-1-ylethyl]prop-2-en-1-amine
  参考文献：
  名称：

  1,5-Asymmetric Induction in Squarate Cascades. Conformational Control of Helicity by Chiral Amino Substituents during Conrotatory Octatetraene Cyclization Prior to β-Elimination

  摘要：

  Both the sigmatropic and electrocyclic rearrangement pathways that can arise when a pair of alkenyl anions are added to a squarate ester have high stereochemical demands. The distinction is nontrivial. When cis addition occurs initially, the stereoinduction that materializes at this point is fully transmitted into the product(s). The more commonly observed trans addition exhibits fleeting stereochemical consequences because of rapid equilibration of the octatetraenyl intermediates. In this instance, product distribution is governed by the relative rates of conrotatory cyclization at this advanced stage. Herein reported is a complete dissection of a squarate cascade when a stereogenic center attached to an amino substituent effects 1,5-asymmetric induction prior to B-elimination of the entire fragment. Deuterium labeling permits a direct measure of the contrasting kinetic imbalances associated with the two possible modes of alkenyl anion addition. Furthermore; quantitative analysis of the partitioning experienced by the two helical octatetraenes is readily accomplished. This work constitutes the first example where a complete dynamic profile for these complex processes has been possible. The fact that long-range asymmetric induction has been instrumental in solving the mechanistic puzzle is noteworthy.

  DOI：

  10.1021/jo9722921
• 作为产物：
  描述：

  1-萘乙胺 生成 N-(R)-1-(1-naphthyl)ethyl methyl carbamate
  参考文献：
  名称：

  Cross-Linked Crystals of Subtilisin:  Versatile Catalyst for Organic Synthesis

  摘要：

  Cross-linked enzyme crystals (CLECs) of subtilisin exhibit excellent activity in aqueous and various organic solvents. This catalyst is more stable than the native enzyme in both aqueous and mixed aqueous/organic solutions. Subtilisin-CLEC was shown to be a versatile catalyst. It was used for the syntheses of peptides and peptidomimetics, mild hydrolysis of amino acid and peptide amides, enantio- and regioselective reactions, and transesterifications.

  DOI：

  10.1021/jo9618334

文献信息

• COMPOUNDS AND METHODS FOR TREATING RESPIRATORY DISEASES
  申请人：Ghosh Arun K.

  公开号：US20110269834A1

  公开（公告）日：2011-11-03

  Described herein are compounds and compositions, and methods for using the compounds and compositions, for treating respiratory diseases and illness, such as severe acute respiratory syndrome (SARS).

  本文描述了化合物和组合物，以及使用这些化合物和组合物治疗呼吸道疾病和疾病，如严重急性呼吸综合征（SARS）的方法。
• Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction
  作者：Marek Stankevič

  DOI：10.1039/c4ob02440k

  日期：——

  Treatment of diarylphosphinous acid-borane amides possessing chiral amido functionality with an alkali metal solution in liquid ammonia induced a preferential dearomatization of one aryl substituent at phosphorus leading to the formation of non-equimolar amounts of diastereomers. Diastereoselectivity of dearomatization depends strongly on the structure of a chiral auxiliary.

  用碱金属溶液在液氨中处理具有手性酰胺基官能团的二芳基次膦酸-硼烷酰胺会诱导一个芳基取代基在磷上优先脱芳香化，导致形成非等摩尔量的非对映异构体。脱芳香化的非对映选择性很大程度上取决于手性助剂的结构。
• Syntheses of Bile Pigments. Part 17. Synthesis of a non-racemizable urobilin derivative
  作者：Lubomir Floch、Fredy Nydegger、Albert Gossauer、Christoph Kratky

  DOI：10.1002/hlca.19940770205

  日期：1994.3.23

  the eleven-step synthesis of 7 is the 1,4,5,10-tetrahydro-10-hydroxy-1-oxo-11H-dipyrrin-9-carboxylate rac-2, which could be resolved into enantiomers by fractional crystallization of the corresponding methyl N-[1-(naphth-1-yl)ethyl]carbamates 3 and 4. The absolute configuration of enantiomerically pure (−)-2 was determined by X-ray diffraction analysis of its camphor-10-sulfonate 5. As the CD spectrum

  合成了具有光学活性的尿嘧啶模型化合物7，其中Me基团代替H原子与不对称中心键合，从而防止了互变异构引起的手性损失。7的11步合成的关键中间体是1,4,5,10-四氢-10-羟基-1-氧代-11 H-二吡喃-9-羧酸盐rac - 2，可通过拆分为对映体N- [1-（萘-1-基）乙基]氨基甲酸甲酯3和4的分步结晶。对映体纯的（-）- 2的绝对构型是通过对其樟脑10磺酸盐的X射线衍射分析确定的5。由于从（-）-（R）-2获得的尿嘧啶类似物7的CD光谱显示出正的Cotton效应，因此，与先前的工作相关，本结果证明，用Me基团取代了与H原子键合的H原子。手性尿嘧啶发色团的不对称中心不影响后者的绝对构型与其螺旋度之间的关系。
• Dynamic kinetic resolution of amines by using palladium nanoparticles confined inside the cages of amine-modified MIL-101 and lipase
  作者：Sen Xu、Meng Wang、Bo Feng、Xinchen Han、Zijie Lan、Huajun Gu、Hexing Li、Hui Li

  DOI：10.1016/j.jcat.2018.04.006

  日期：2018.7

  Dynamic kinetic resolution (DKR) of amines is an important strategy for the synthesis of chiral drugs and their building blocks; however, improving the matchability of metal-catalyzed racemization and enzymatic resolution is still a task. In this paper, Pd nanoparticles (NPs) were encapsulated inside the cages of ethylenediamine-grafted MIL-101 (ED-MIL-101), giving highly efficient catalysts (Pd/ED-MIL-101)

  胺的动态动力学拆分（DKR）是合成手性药物及其结构单元的重要策略；然而，改善金属催化的外消旋和酶促拆分的匹配性仍然是一项任务。本文将Pd纳米颗粒（NPs）封装在乙二胺接枝的MIL-101（ED-MIL-101）的笼内，从而为伯胺的外消旋化提供了高效的催化剂（Pd / ED-MIL-101）。外消旋可与脂肪酶催化的拆分反应结合在rac -1-苯乙胺的一锅DKR中，得到光学纯的产物（ee大于99％最高的转化率和选择性分别高达99％和93％，优于其他催化剂，例如Pd / MIL-101，Pd / MCM-41和市售Pd / C。此外，非均相化学酶催化剂组合可以被回收和再循环8次而没有明显的效率损失。发现增强的催化性能取决于MIL-101的胺修饰，该修饰不仅赋予其笼罩表面以基本性质，而且使之能够有效地将笼罩中的Pd NPs限制在笼罩内。另外，可以通过在微波辐射下进行DKR工艺来进一步增强这种化学酶催化剂组合的匹配性。
• Structure-Based Design, Synthesis, and Biological Evaluation of a Series of Novel and Reversible Inhibitors for the Severe Acute Respiratory Syndrome−Coronavirus Papain-Like Protease
  作者：Arun K. Ghosh、Jun Takayama、Yoann Aubin、Kiira Ratia、Rima Chaudhuri、Yahira Baez、Katrina Sleeman、Melissa Coughlin、Daniel B. Nichols、Debbie C. Mulhearn、Bellur S. Prabhakar、Susan C. Baker、Michael E. Johnson、Andrew D. Mesecar

  DOI：10.1021/jm900611t

  日期：2009.8.27

  We describe here the design, Synthesis, molecular modeling. and biological evaluation of a series of small molecule, nonpeptide inhibitors of SARS-CoV PLpro. Our initial lead compound was identified via high-throughput screening of a diverse chemical library. We subsequently carried out structure-activity relationship studies and optimized the lead structure to potent inhibitors that have shown antiviral activity against SARS-CoV infected Vero E6 cells, Upon the basis of the X-ray crystal structure of inhibitor 24-bound to SARS-CoV PLpro, a drug design template was created. Our structure-based modification led to the design of a more potent inhibitor, 2 (enzyme IC50 = 0.46 mu M; antiviral EC50 = 6 mu M). Interestingly. its methylamine derivative, 49, displayed good enzyme inhibitory potency (IC50 = 1.3 mu M) and the most potent SARS antiviral activity (EC50 = 5.2 mu M) in the series, We have carried our computational docking studies and generated a predictive 3D-QSAR model for SARS-CoV PLpro inhibitors.