benzyl N-[(2R)-1-hydroxy-6,6-dimethoxyhexan-2-yl]-N-(phenylmethoxycarbonylamino)carbamate | 1108747-25-6

• 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: benzyl N-[(2R)-1-hydroxy-6,6-dimethoxyhexan-2-yl]-N-(phenylmethoxycarbonylamino)carbamate
• CAS: 1108747-25-6
• 化学式: C₂₄H₃₂N₂O₇
• 分子量: 460.527
• InChiKey: MXVURCIIPDYWQL-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2R)-1-hydroxy-6,6-dimethoxyhexan-2-yl]-N-(phenylmethoxycarbonylamino)carbamate 、 三氟乙酸 在 palladium on activated charcoal 、 氢气 、 镍 、 PtO₂*H₂O 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 以95%的产率得到2-hydroxymethylpiperidinium trifluoroacetate
  参考文献：
  名称：

  Efficient syntheses of enantioenriched (R)-pipecolic acid and (R)-proline via electrophilic organocatalytic amination

  摘要：

  Five-step syntheses of (R)-pipecolic acid and (R)-proline are described, respectively, from cyclohexene and cyclopentene. The key step involves the ganocatalytic alpha-amination of functionalized aldehydes. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.054
• 作为产物：
  描述：

  1,1,6,6-四甲氧基己烷 、 偶氮二甲酸二苄酯 在 氯乙酸 、 三氟乙酸 、 (S)-5-(吡咯烷-2-基)-1H-四唑 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 水 、 乙醇 为溶剂， 反应 22.25h， 以78%的产率得到benzyl N-[(2R)-1-hydroxy-6,6-dimethoxyhexan-2-yl]-N-(phenylmethoxycarbonylamino)carbamate
  参考文献：
  名称：

  Acetals: a new organocatalysis chemotype for one-pot enantioselective α-amination

  摘要：

  Conditions are described for one-pot Bronsted acid and organocatalysed enantioselective alpha-amination of acetals and associated functionalities. Of the organocatalysts screened, proline tetrazole gave the highest ee, while aqueous monochloroacetic acid proved to be the best Bronsted acid activator regarding minimizing racemization and maximizing product yield. The reaction opens up the way for using masked carbonyl functionalities in organocatalysis. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.097

文献信息

• Asymmetric α-Amination of Aldehydes and Ketones Catalyzed by tert-Butoxy-L-Proline
  作者：Ramzi Ait-Youcef、Delphine Kalch、Xavier Moreau、Christine Thomassigny、Christine Greck

  DOI：10.2174/157017809788681293

  日期：2009.7.1

  Asymmetric electrophilic α-amination of aldehydes and ketones is described using trans-3-tert-butoxy-Lproline and trans-4-tert-butoxy-L-proline as efficient catalysts. Good yields and high enantioselectivities are obtained working at 0°C or at room temperature with a catalyst loading of only 5 mol%.

  以反式-3-叔丁氧基-L-脯氨酸和反式-4-叔丁氧基-L-脯氨酸为高效催化剂，描述了醛和酮的不对称亲电α-氨基化反应。在 0°C 或室温条件下，催化剂负载量仅为 5 摩尔%，即可获得良好的产率和较高的对映选择性。
• Organocatalytic asymmetric syntheses of functionalized tetrahydropyridazines
  作者：Delphine Kalch、Ramzi Ait Youcef、Xavier Moreau、Christine Thomassigny、Christine Greck

  DOI：10.1016/j.tetasy.2010.07.030

  日期：2010.9

  Four tetrahydropyridazines, respectively, substituted at the C-3 position with hydroxymethyl, a silyloxymethyl, a carboxylic acid, and a methyl ester have been prepared in good yields and high enantiomeric purities using organocatalytic alpha-amination of aldehydes as the key step. These compounds have then been tested as organocatalysts for the same reaction. (C) 2010 Elsevier Ltd. All rights reserved.
• Acetals: a new organocatalysis chemotype for one-pot enantioselective α-amination
  作者：Ath’enkosi Msutu、Roger Hunter

  DOI：10.1016/j.tetlet.2014.02.097

  日期：2014.4

  Conditions are described for one-pot Bronsted acid and organocatalysed enantioselective alpha-amination of acetals and associated functionalities. Of the organocatalysts screened, proline tetrazole gave the highest ee, while aqueous monochloroacetic acid proved to be the best Bronsted acid activator regarding minimizing racemization and maximizing product yield. The reaction opens up the way for using masked carbonyl functionalities in organocatalysis. (C) 2014 Elsevier Ltd. All rights reserved.
• Efficient syntheses of enantioenriched (R)-pipecolic acid and (R)-proline via electrophilic organocatalytic amination
  作者：Delphine Kalch、Nicolas De Rycke、Xavier Moreau、Christine Greck

  DOI：10.1016/j.tetlet.2008.11.054

  日期：2009.1

  Five-step syntheses of (R)-pipecolic acid and (R)-proline are described, respectively, from cyclohexene and cyclopentene. The key step involves the ganocatalytic alpha-amination of functionalized aldehydes. (C) 2008 Elsevier Ltd. All rights reserved.