(2S)-2-[benzyl(methyl)amino]-2-phenylethan-1-ol | 573701-29-8

• 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: (2S)-2-[benzyl(methyl)amino]-2-phenylethan-1-ol
• 英文别名: (2S)-N-benzyl-N-methyl-2-phenylglycinol；(2S)-2-[benzyl(methyl)amino]-2-phenylethanol
• CAS: 573701-29-8
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: SNUUNSDZCIEWPI-MRXNPFEDSA-N

物化性质

• 沸点：
  354.7±27.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-[benzyl(methyl)amino]-2-phenylethan-1-ol 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 氯仿 为溶剂， 以43%的产率得到benzyl[(2R)-2-bromo-2-phenylethyl]methylamine
  参考文献：
  名称：

  氮丙啶鎓离子的立体选择性和区域选择性分子内傅克反应合成 4-取代四氢异喹啉

  摘要：

  通过氮丙啶鎓离子的分子内弗里德尔-克来福特 (FC) 反应以高度区域和立体选择性方式合成了光学活性 4-取代四氢异喹啉。对照实验表明氮丙啶鎓离子的形成和开环是路易斯酸催化 FC 反应中的关键中间体。

  DOI：

  10.1021/ol4013537
• 作为产物：
  描述：

  (2S)-N-benzyl-N-methyl-2-phenylglycine methyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以92%的产率得到(2S)-2-[benzyl(methyl)amino]-2-phenylethan-1-ol
  参考文献：
  名称：

  L-氨基酸的“ N-立体异构季铵盐”：合成，分离和绝对构型

  摘要：

  Abstractmagnified imageDiastereoisomeric linear and cyclic ‘N‐chiral quaternary ammonium salts’ (QASs) were efficiently synthesized from corresponding L‐amino acids in high yields. The diastereoisomers of each pair of ‘N‐chiral QASs’ were successfully separated. The absolute configurations of these QASs were determined predominately by X‐ray single‐crystal analysis. The 1H‐NMR data of ‘N‐chiral QASs’ provided characteristic information on the configuration of the N‐chiral center. ‘N‐Chiral QASs’ exemplified by [N(R)]‐2a and [N(S)]‐2a are stable in protic and aprotic solvents within a broad pH and temperature range.

  DOI：

  10.1002/hlca.200800326

文献信息

• Stereoselective formation and rearrangement of morpholinium ylides derived from copper carbenoids
  作者：Kevin W. Glaeske、B.N. Naidu、F.G. West

  DOI：10.1016/s0957-4166(03)00095-8

  日期：2003.4

  Amino diazoacetoacetates 4a–e and 7a,b were prepared from readily available amino alcohols and subjected to copper-catalyzed carbene-transfer reaction. Substrates 4c–e furnished the morpholin-2-ones 5c–e in good yield via the corresponding cyclic ammonium ylides, albeit with poor diastereoselectivity. Substrates 4a,b failed to provide the corresponding morpholinones, perhaps as a result of steric congestion

  氨基重氮乙酰乙酸酯4a – e和7a，b由容易获得的氨基醇制备，并进行铜催化的卡宾转移反应。尽管非对映选择性差，但底物4c – e通过相应的环状铵盐以高收率提供了吗啉-2-酮5c – e。底物4a，b可能不能提供相应的吗啉酮，这可能是由于空间拥挤的结果。环状底物7a，b经历转化为双环吗啉酮8和9收率高，非对映选择性中等。通过控制中间双环烷基化物的瞬时立体异构的铵中心，可以合理化该结果。
• Stereoselective and Regioselective Intramolecular Friedel–Crafts Reaction of Aziridinium Ions for Synthesis of 4-Substituted Tetrahydroisoquinolines
  作者：Hyun-Soon Chong、Yunwei Chen

  DOI：10.1021/ol4013537

  日期：2013.12.6

  Optically active 4-substituted tetrahydroisoquinolines were synthesized via intramolecular Friedel–Crafts (FC) reactions of aziridinium ions in a highly regio- and stereoselective manner. Control experiments suggest the formation and ring-opening of aziridinium ions as the key intermediates in the Lewis acid catalyzed FC reactions.

  通过氮丙啶鎓离子的分子内弗里德尔-克来福特 (FC) 反应以高度区域和立体选择性方式合成了光学活性 4-取代四氢异喹啉。对照实验表明氮丙啶鎓离子的形成和开环是路易斯酸催化 FC 反应中的关键中间体。
• ‘N-Stereogenic Quaternary Ammonium Salts’ from L-Amino Acids: Synthesis, Separation, and Absolute Configuration
  作者：Hua-Fang Wu、Wen-Bin Lin、Li-Zi Xia、Ying-Gang Luo、Xiao-Zhen Chen、Guo-You Li、Guo-Lin Zhang、Xin-Fu Pan

  DOI：10.1002/hlca.200800326

  日期：2009.4

  Abstractmagnified imageDiastereoisomeric linear and cyclic ‘N‐chiral quaternary ammonium salts’ (QASs) were efficiently synthesized from corresponding L‐amino acids in high yields. The diastereoisomers of each pair of ‘N‐chiral QASs’ were successfully separated. The absolute configurations of these QASs were determined predominately by X‐ray single‐crystal analysis. The 1H‐NMR data of ‘N‐chiral QASs’ provided characteristic information on the configuration of the N‐chiral center. ‘N‐Chiral QASs’ exemplified by [N(R)]‐2a and [N(S)]‐2a are stable in protic and aprotic solvents within a broad pH and temperature range.