(2S,3S)-3-hydroxy-2-(N-methylamino)-4-pentene | 143817-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S)-3-hydroxy-2-(N-methylamino)-4-pentene
• 英文别名: (3S,4S)-4-(methylamino)pent-1-en-3-ol
• CAS: 143817-98-5
• 化学式: C₆H₁₃NO
• 分子量: 115.175
• InChiKey: WZAVYHKCQFHNPT-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-hydroxy-2-(N-methylamino)-4-pentene 在 lithium aluminium tetrahydride 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 13.0h， 生成 (2S,6S)-N,2-dimethyl-6-(hydroxymethyl)-1,2,5,6-tetrahydropyridine
  参考文献：
  名称：

  An efficient stereoselective synthesis of .DELTA.4,5-pipecolic esters

  摘要：

  The synthesis of racemic and enantiomerically homogeneous pipecolic esters from 1-amino-3-buten-2-ols is reported. The synthesis of enantiomerically homogeneous N-methylpipecolic esters requires four chemical steps from N-t-BOC-protected amino esters. The key step of the sequence is a conformationally restricted Claisen rearrangement. The method affords complete control of the absolute and relative stereochemistry of all three stereogenic centers in pipecolic ester 22 which is obtained in 33% overall yield from N-t-BOC-L-alanine ethyl ester 16a.

  DOI：

  10.1021/jo00048a030
• 作为产物：
  描述：

  tert-butyl (2S)-3-hydroxypent-4-en-2-ylcarbamate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (2S,3R)-3-hydroxy-2-(N-methylamino)-4-pentene 、 (2S,3S)-3-hydroxy-2-(N-methylamino)-4-pentene
  参考文献：
  名称：

  An efficient stereoselective synthesis of .DELTA.4,5-pipecolic esters

  摘要：

  The synthesis of racemic and enantiomerically homogeneous pipecolic esters from 1-amino-3-buten-2-ols is reported. The synthesis of enantiomerically homogeneous N-methylpipecolic esters requires four chemical steps from N-t-BOC-protected amino esters. The key step of the sequence is a conformationally restricted Claisen rearrangement. The method affords complete control of the absolute and relative stereochemistry of all three stereogenic centers in pipecolic ester 22 which is obtained in 33% overall yield from N-t-BOC-L-alanine ethyl ester 16a.

  DOI：

  10.1021/jo00048a030

文献信息

• An efficient stereoselective synthesis of .DELTA.4,5-pipecolic esters
  作者：Steven R. Angle、J. Guy Breitenbucher、Damian O. Arnaiz

  DOI：10.1021/jo00048a030

  日期：1992.10

  The synthesis of racemic and enantiomerically homogeneous pipecolic esters from 1-amino-3-buten-2-ols is reported. The synthesis of enantiomerically homogeneous N-methylpipecolic esters requires four chemical steps from N-t-BOC-protected amino esters. The key step of the sequence is a conformationally restricted Claisen rearrangement. The method affords complete control of the absolute and relative stereochemistry of all three stereogenic centers in pipecolic ester 22 which is obtained in 33% overall yield from N-t-BOC-L-alanine ethyl ester 16a.