(9H-fluoren-9-yl)methyl 4-chlorobenzoyloxycarbamate | 1262306-23-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (9H-fluoren-9-yl)methyl 4-chlorobenzoyloxycarbamate
• 英文别名: (9H-fluoren-9-ylmethoxycarbonylamino) 4-chlorobenzoate
• CAS: 1262306-23-9
• 化学式: C₂₂H₁₆ClNO₄
• 分子量: 393.826
• InChiKey: AOYCDPXHUWAVDB-UHFFFAOYSA-N

物化性质

• 熔点：
  156 °C
• 密度：
  1.346±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl 4-chlorobenzoyloxycarbamate 、 Methyl cinnamate 在 四氧化锇 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 乙腈 、 水 为溶剂， 反应 0.17h， 以58%的产率得到methyl (2S,3R)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  Alkyl 4-Chlorobenzoyloxycarbamates as Highly Effective Nitrogen Source Reagents for the Base-Free, Intermolecular Aminohydroxylation Reaction

  摘要：

  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.

  DOI：

  10.1021/jo1018816
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 在 盐酸羟胺 、 碳酸氢钠 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 1.17h， 生成 (9H-fluoren-9-yl)methyl 4-chlorobenzoyloxycarbamate
  参考文献：
  名称：

  [EN] IMPROVED AMINOHYDROXYLATION OF ALKENES
  [FR] AMINOHYDROXYLATION AMÉLIORÉE D'ALCÈNES

  摘要：

  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。

  公开号：

  WO2011159177A1

文献信息

• Asymmetric Synthesis of Fmoc-Protected β-Hydroxy and β-Methoxy Amino Acids via a Sharpless Aminohydroxylation Reaction Using FmocNHCl
  作者：Ryan Moreira、Scott D. Taylor

  DOI：10.1021/acs.orglett.8b03458

  日期：2018.12.7

  An efficient asymmetric synthesis of l-threo-β-hydroxyasparagine and l-threo-β-methoxyaspartate that are suitably protected for Fmoc solid phase peptide synthesis is described. The key step in these syntheses was a Sharpless asymmetric aminohydroxylation reaction under basic conditions using N-chlorofluorenyl carbamate (FmocNHCl), a readily prepared and storable nitrogen source.

  的有效不对称合成升-苏-β-hydroxyasparagine和升-苏-β-methoxyaspartate被适当地用于Fmoc固相肽合成的保护进行说明。这些合成的关键步骤是在碱性条件下使用易于制备且可存储的氮源N-氯芴基氨基甲酸酯（FmocNHCl）在Sharpless上进行不对称的氨基羟基化反应。
• 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。
• Aminohydroxylation of alkenes
  申请人：Mee Simon Peter Harold

  公开号：US08987504B2

  公开（公告）日：2015-03-24

  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）对烯烃进行氨羟化反应的方法。本发明特别涉及在无添加碱的情况下进行的分子间氨羟化反应。本发明还涉及新型N-氧化氨酸酯试剂，其为稳定的晶体材料。本发明的方法在合成具有邻二醇氨基基团的化合物方面有用，例如生物活性化合物。
• US8987504B2
  申请人：——

  公开号：US8987504B2

  公开（公告）日：2015-03-24
• 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.