(2R,5S)-5-benzyl-2-methyl-4-(4-methylphenyl)sulfonylmorpholine | 1352166-09-6

• 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: (2R,5S)-5-benzyl-2-methyl-4-(4-methylphenyl)sulfonylmorpholine
• CAS: 1352166-09-6
• 化学式: C₁₉H₂₃NO₃S
• 分子量: 345.463
• InChiKey: GCYSUFSZSGPPHZ-AEFFLSMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-N-allyl-N-(1-hydroxy-3-phenylpropan-2-yl)-4-methylbenzenesulfonamide 在 lithium aluminium tetrahydride 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 (2R,5S)-5-benzyl-2-methyl-4-(4-methylphenyl)sulfonylmorpholine
  参考文献：
  名称：

  I₂-Mediated Diversity Oriented Diastereoselective Synthesis of Amino Acid Derived trans-2,5-Disubstituted Morpholines, Piperazines, and Thiomorpholines

  摘要：

  Diastereoselective trans-2,5-disubstituted amino acids derived diverse morpholines, piperazines and thiomorpholines were prepared in 30 min-1 h with high yields through iodine-mediated 6-exotrig type cyclization from a single common synthetic intermediate. The displacement of iodine with hydride ion gave a methyl substituent at the 2-position of morpholines which provides an additional opportunity for diversity oriented nucleophilic substitution on the rings as well as incorporation of substituents at the 5-position from amino acids constituents.

  DOI：

  10.1021/co200129t

文献信息

• I₂-Mediated Diversity Oriented Diastereoselective Synthesis of Amino Acid Derived <i>trans</i>-2,5-Disubstituted Morpholines, Piperazines, and Thiomorpholines
  作者：Saurav Bera、Gautam Panda

  DOI：10.1021/co200129t

  日期：2012.1.9

  Diastereoselective trans-2,5-disubstituted amino acids derived diverse morpholines, piperazines and thiomorpholines were prepared in 30 min-1 h with high yields through iodine-mediated 6-exotrig type cyclization from a single common synthetic intermediate. The displacement of iodine with hydride ion gave a methyl substituent at the 2-position of morpholines which provides an additional opportunity for diversity oriented nucleophilic substitution on the rings as well as incorporation of substituents at the 5-position from amino acids constituents.