(+)-(2R,3S)-methyl 3-(ethoxycarbonylamino)-2-hydroxy-3-phenylpropanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+)-(2R,3S)-methyl 3-(ethoxycarbonylamino)-2-hydroxy-3-phenylpropanoate
• 英文别名: methyl (2R,3S)-3-(ethoxycarbonylamino)-2-hydroxy-3-phenylpropanoate
• 化学式: C₁₃H₁₇NO₅
• 分子量: 267.282
• InChiKey: XHHWXGAOTLHODC-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Methyl cinnamate 、 ethyl N-chloro-N-sodiocarbamate 在 Hydroquinone 1,4-phthalazinediyl diether 、 potassium dioxotetrahydroxoosmate(VI) 、 水 作用下， 以 丙醇 为溶剂， 反应 0.75h， 以78%的产率得到(+)-(2R,3S)-methyl 3-(ethoxycarbonylamino)-2-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  Li, Guigen; Angert, Hubert H.; Sharpless, K. Barry, Angewandte Chemie, 1996, vol. 108, # 23/24, p. 2995 - 2999

  摘要：

  DOI：

文献信息

• Osmium-Catalyzed Vicinal Oxyamination of Alkenes by <i>N</i>-(4-Toluenesulfonyloxy)carbamates
  作者：Masruri、Anthony C. Willis、Malcolm D. McLeod

  DOI：10.1021/jo301372y

  日期：2012.10.5

  N-(4-Toluenesulfonyloxy)carbamates based on a range of common amine protecting groups serve as preformed nitrogen sources in the intermolecular osmium-catalyzed oxyamination reaction of a variety of mono-, di-, and trisubstituted alkenes. The reactions occur with low catalyst loadings and good yields and afford high regioselectivity for unsymmetrically substituted alkenes.

  在一系列单，二和三取代烯烃的分子间催化的氧化胺化反应中，基于一系列常见胺保护基的N-（4-甲苯磺酰氧基）氨基甲酸酯用作预制的氮源。该反应以低的催化剂负载量和良好的收率进行，并且对于不对称取代的烯烃提供高的区域选择性。
• [EN] IMPROVED AMINOHYDROXYLATION OF ALKENES<br/>[FR] AMINOHYDROXYLATION AMÉLIORÉE D'ALCÈNES
  申请人：IND RES LTD

  公开号：WO2011159177A1

  公开（公告）日：2011-12-22

  The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.

  该发明涉及一种使用N-氧羰酸酯试剂（例如N-酰氧羰酸酯、N-烷氧羰酸酯和N-芳基氧羰酸酯试剂）对烯烃进行氨羟基化的方法。该发明特别涉及一种可以在无需添加碱的情况下进行的分子间氨羟基化反应。该发明还涉及新颖的N-氧羰酸酯试剂，这些试剂是稳定的结晶材料。该发明的方法在合成具有邻位氨基醇基团的化合物方面非常有用，例如具有生物活性的化合物。
• Heterogeneous asymmetric aminohydroxylation of alkenes using a silica gel-supported bis-cinchona alkaloid
  作者：Choong Eui Song、Chun Rim Oh、Sung Woo Lee、Sang-gi Lee、Laetitia Canali、David C. Sherrington

  DOI：10.1039/a806959j

  日期：——

  Excellent enantioselectivities of up to >99% ee have been achieved in the heterogeneous asymmetric aminohydroxylation of trans-cinnamate derivatives using silica gel-supported (QN)2PHAL [SGS-(QN)2PHAL 1]; the dark brown 1·Os complex, recovered by simple filtration after reaction, could be reused without any loss of enantioselectivity.

  在使用硅胶支撑的 (QN)2PHAL [SGS-(QN)2PHAL 1] 进行反式肉桂酸酯衍生物的异相不对称氨基羟基化反应中，实现了高达 >99% ee 的优异对映选择性；反应后通过简单过滤回收的深棕色 1-Os 复合物可重复使用，而不会损失任何对映选择性。
• AMINOHYDROXYLATION OF ALKENES
  申请人：Mee Simon Peter Harold

  公开号：US20130274479A1

  公开（公告）日：2013-10-17

  The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.

  本发明涉及使用N-氧化氨基甲酸酯试剂（例如N-酰氧基氨基甲酸酯、N-烷氧羰氧甲酸酯和N-芳烃氧羰氧甲酸酯试剂）进行烯烃氨基羟化的方法。本发明特别涉及可以在无添加碱的情况下进行的分子间氨基羟化反应。本发明还涉及新颖的N-氧化氨基甲酸酯试剂，其为稳定的晶体材料。本发明的方法在合成具有邻位氨基醇基团的化合物（例如具有生物活性的化合物）方面非常有用。
• Alkyl 4-Chlorobenzoyloxycarbamates as Highly Effective Nitrogen Source Reagents for the Base-Free, Intermolecular Aminohydroxylation Reaction
  作者：Lawrence Harris、Simon P. H. Mee、Richard H. Furneaux、Graeme J. Gainsford、Andreas Luxenburger

  DOI：10.1021/jo1018816

  日期：2011.1.21

  Ethyl- (7), benzyl- (8), tert-butyl- (9), and fluorenylmethyl-4-chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.