ethyl (1R)-2-hydroxy-1-phenylethylcarbamate | 161533-41-1

• 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: ethyl (1R)-2-hydroxy-1-phenylethylcarbamate
• 英文别名: ethyl N-[(1R)-2-hydroxy-1-phenylethyl]carbamate
• CAS: 161533-41-1
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: GGXTXKPEZSYEOB-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (1R)-2-hydroxy-1-phenylethylcarbamate 在 lithium aluminium tetrahydride 、 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 11.0h， 以36%的产率得到(R)-2-(甲基氨基)-2-苯基乙醇
  参考文献：
  名称：

  TNF-α产生的高效抑制剂。第二部分：新发现的化学铅的代谢稳定性和活性非对映异构体的构象分析。

  摘要：

  据报道可能是新药候选者的代谢稳定的TNF-α抑制剂的设计和合成。基于构象固定的茚满衍生物17和18的生物学评价，进行了活性非对映异构体的构象分析。还讨论了基于光学活性衍生物的生物学评价的构效关系（SAR）。报告了包括化学在内的全部详细信息。

  DOI：

  10.1016/s0968-0896(02)00380-2
• 作为产物：
  描述：

  methyl (R)-N-(ethoxycarbonyl)-phenylglycinate 在 sodium tetrahydroborate 、 calcium chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以96%的产率得到ethyl (1R)-2-hydroxy-1-phenylethylcarbamate
  参考文献：
  名称：

  从 α-氨基酸制备手性 2-恶唑烷酮的简单有效方法

  摘要：

  摘要 描述了标题转化的改进程序，它避免了：(i) 潜在危险的硼烷还原步骤，和 (ii) 水溶性氨基醇的中间体。

  DOI：

  10.1080/00397919508011390

文献信息

• Modified Mg : Al hydrotalcite in the synthesis of oxazolidin-2-ones
  作者：Agnieszka Cwik、Aliz Fuchs、Zoltán Hell、Ildikó Böjtös、Dóra Halmai、Petra Bombicz

  DOI：10.1039/b418848a

  日期：——

  The modified Mg : Al (3 : 1) hydrotalcite has been found to be an efficient catalyst in the conversion of carbamates into oxazolidin-2-ones under mild reaction conditions. A wide variety of oxazolidin-2-ones were obtained with excellent chemical yield.

  改性Mg : Al（3 : 1）水滑石已被证实是一种高效催化剂，在温和反应条件下能将氨基甲酸酯转化为噁唑烷-2-酮。多种噁唑烷-2-酮以优异的化学产率获得。
• Synthesis and Characterization of Tetrahedral Ru₃O Clusters with Intrinsic Framework Chirality:  A Chiral Probe of the Intact Cluster Catalysis Concept
  作者：Ludovic Vieille-Petit、Georg Süss-Fink、Bruno Therrien、Thomas R. Ward、Helen Stœckli-Evans、Gaël Labat、Lydia Karmazin-Brelot、Antonia Neels、Thomas Bürgi、Richard G. Finke、Collin M. Hagen

  DOI：10.1021/om050643t

  日期：2005.12.1

  intact trinuclear arene ruthenium clusters containing an oxo cap, cationic Ru3O clusters with three different arene ligands (intrinsically chiral tetrahedra) have been synthesized as racemic mixtures. By introduction of a chiral auxiliary substituent at one of the three different arene ligands, the separation of the two diastereomers was possible. The chiral Ru3O framework was evidenced by X-ray crystallography

  为了提供证据支持或反对通过完整的含氧代帽的三核芳烃钌簇进行催化氢化的假说，已将具有三种不同芳烃配体的阳离子Ru 3 O簇（本征上为手性四面体）合成为外消旋混合物。通过在三个不同的芳烃配体之一处引入手性辅助取代基，可以分离两种非对映异构体。X射线晶体学，UV和IR区域的圆二色性以及NMR光谱中的手性位移试剂证明了手性Ru 3 O骨架。使用手性Ru 3催化前手性底物2-乙酰氨基丙烯酸甲酯的氢化反应O团簇未显示不对称诱导，表明催化活性物种不是完整的Ru 3 O团簇。
• [EN] SYNTHESIS OF OXAZOLINE COMPOUNDS<br/>[FR] SYNTHÈSE DE COMPOSÉS D'OXAZOLINE
  申请人：UNIV HONG KONG POLYTECHNIC

  公开号：WO2010015211A1

  公开（公告）日：2010-02-11

  The present invention provides an improved process for preparing an oxazoline compound of the formula: (I) wherein R1 and R2 are independently hydrogen, sulfide, sulfoxide, sulfonyl, optionally substituted lower alkyl, optionally substituted aralkyl, optionally substituted aryl or optionally substituted polycyclic arylyl; or R1 and R2 combined together with the carbon atoms to which they are attached form an optionally substituted fused 6-member aromatic ring provided that R1 and R2 are attached to carbon atoms adjacent to each other; and R3 is hydrogen, sulfide, sulfoxide, sulfonyl, optionally substituted lower alkyl, optionally substituted aralkyl, optionally substituted aryl or optionally substituted polycyclic arylyl; or an enantiomer therof; or an enantiomeric mixture therof; comprising the step of contacting an acylamino alcohol compound to a suitable amount of fluoroalkanesulfonyl fluoride compound and organic basic reagent. By using a fluoroalkanesulfonyl fluoride compound with an organic basic reagent, the present invention efficiently converts acylamino alcohol compounds into highly chemoselective oxazoline compounds with a remarkable variety of substrates, mild conditions and relatively short reaction time.

  本发明提供了一种改进的制备氧杂环丙烯酮化合物的方法，其化学式为：(I)，其中R1和R2分别为氢、硫化物、亚氧化物、磺酰基、可选择取代的较低烷基、可选择取代的芳基烷基、可选择取代的芳基或可选择取代的多环芳基；或者R1和R2与它们附着的碳原子结合在一起形成可选择取代的融合6-环芳香环，前提是R1和R2附着在彼此相邻的碳原子上；而R3为氢、硫化物、亚氧化物、磺酰基、可选择取代的较低烷基、可选择取代的芳基烷基、可选择取代的芳基或可选择取代的多环芳基；或其对映体；或其对映体混合物；包括将酰胺醇化合物与适量的氟代烷磺酰氟化合物和有机碱性试剂接触的步骤。通过使用氟代烷磺酰氟化合物和有机碱性试剂，本发明能够高效地将酰胺醇化合物转化为高度化学选择性的氧杂环丙烯酮化合物，适用于多种底物，反应条件温和，反应时间相对较短。
• Asymmetric aminohydroxylation of substituted styrenes: applications in the synthesis of enantiomerically enriched arylglycinols and a diamine
  作者：Peter O’Brien、Simon A. Osborne、Daniel D. Parker

  DOI：10.1039/a803821j

  日期：——

  The catalytic asymmetric aminohydroxylation of a variety of styrene derivatives and vinyl aromatics using osmium tetroxide in conjunction with alkaloid-derived ligands [e.g. (DHQ)2PHAL or (DHQD)2PHAL] and haloamine salts of alkyl carbamates (e.g. ethyl carbamate or tert-butyl carbamate) has been investigated. By observing the effect of different aromatic substituents and alkyl carbamates on the regioselectivity, yield and enantioselectivity of the aminohydroxylation reactions, a number of conclusions have been reached: (i) the 1-aryl-2-hydroxyethylamine regioisomers were obtained as the major products in reasonable yield and high (87%) enantiomeric excess; (ii) tert-butyl carbamate was superior to ethyl carbamate in terms of yield, enantioselectivity and ease of removal of the N-protecting group; (iii) high (96%) enantioselectivity was observed with a 4-methoxy-substituted styrene whereas ortho-substituted styrenes gave lower enantioselectivities; (iv) chiral ligands (DHQ)2PHAL and (DHQD)2PHAL gave essentially equal and opposite senses and degrees of asymmetric induction; (v) regioselectivity was ligand dependent with better regioselectivity (and therefore higher isolated yields) obtained with (DHQ)2PHAL than with (DHQD)2PHAL. The products of the aminohydroxylation reactions were used to prepare enantiomerically enriched arylglycinols and a chiral diamine.

  研究人员使用四氧化锇与生物碱衍生配体[如 (DHQ)2PHAL 或 (DHQD)2PHAL] 以及氨基甲酸烷基酯的卤胺盐（如氨基甲酸乙酯或氨基甲酸叔丁酯）共同催化多种苯乙烯衍生物和乙烯基芳烃的不对称氨基羟基化反应。通过观察不同芳香取代基和烷基氨基甲酸酯对氨基羟化反应的区域选择性、产率和对映选择性的影响，得出了一些结论：(i) 主要产物为 1-芳基-2-羟乙基胺，产率合理，对映体过量率高（87%）；(ii) 氨基甲酸叔丁酯在产率、对映体选择性和 N-保护基的易去除性方面优于氨基甲酸乙酯；(iii) 4-甲氧基取代苯乙烯的对映选择性高（96%），而正交取代苯乙烯的对映选择性较低；(iv) 手性配体(DHQ)2PHAL 和(DHQD)2PHAL 的不对称诱导作用和程度基本相同；(v) 区域选择性与配体有关，(DHQ)2PHAL 比 (DHQD)2PHAL 的区域选择性更好（因此分离产率更高）。氨基羟化反应的产物被用于制备对映体富集的芳基甘氨醇和手性二胺。
• Ligand-free Ullmann-type arylation of oxazolidinones by diaryliodonium salts
  作者：Ekaterina V. Podrezova、Alina A. Okhina、Artem D. Rogachev、Sergey V. Baykov、Andreas Kirschning、Mekhman S. Yusubov、Natalia S. Soldatova、Pavel S. Postnikov

  DOI：10.1039/d2ob02122f

  日期：——

  the copper-catalyzed N-arylation of hindered oxazolidinones using diaryliodonium salts. The method succeeds in good to excellent yields for the arylation of 4-alkyloxazolidinones, including sterically hindered isopropyl- and tert-butyl-substituted. The efficiency of the method was demonstrated for a wide range of diaryliodonium salts – symmetric and unsymmetric as well as ortho-substituted derivatives

  氮杂杂环的芳基化可被认为是制备各种生物活性化合物最重要的过程之一。在目前的工作中，我们描述了一种使用二芳基碘盐对受阻恶唑烷酮进行铜催化N-芳基化的方法。该方法成功实现了 4-烷基恶唑烷酮的芳基化，包括空间位阻的异丙基和叔丁基取代的化合物。该方法的有效性在广泛的二芳基碘盐（对称和不对称以及邻位）中得到了证明-取代的衍生物。所开发的方法将为开发和制备含有恶唑烷酮部分的新型药物和生物活性分子做出重要贡献。