(3R,5R)-methyl 3-(benzylthio-methyl)-3-methyl-2-oxo-5-phenylmorpholine-4-carboxylate | 1367363-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (3R,5R)-methyl 3-(benzylthio-methyl)-3-methyl-2-oxo-5-phenylmorpholine-4-carboxylate
• 英文别名: methyl (3R,5R)-3-(benzylsulfanylmethyl)-3-methyl-2-oxo-5-phenylmorpholine-4-carboxylate
• CAS: 1367363-42-5
• 化学式: C₂₁H₂₃NO₄S
• 分子量: 385.484
• InChiKey: KRPWIROFVMDYGW-RXVVDRJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,5R)-methyl 3-(benzylthio-methyl)-3-methyl-2-oxo-5-phenylmorpholine-4-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到(R)-5-(benzylthiomethyl)-1-((R)-2-hydroxy-1-phenylethyl)-5-methylimidazolidine-2,4-dione
  参考文献：
  名称：

  Stereoselective synthesis of a dialkylhydantoin featuring an asymmetric Strecker reaction on an acyclic dialkyl ketone

  摘要：

  A diastereoselective Strecker reaction using (R)-(-)-phenylglycinol forms the basis of a concise scalemic route to dialkylhydantoin 1. The phenylglycinol functionality was exploited in the manipulation of the aminonitrile Strecker product through to the dialkylhydantoin via a short, efficient sequence involving crystalline intermediates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.008
• 作为产物：
  描述：

  (R)-2-benzylsulfanylmethyl-2-methyl-4-phenyl-oxazolidine 在 盐酸 、 lithium hydride 、 magnesium bromide ethyl etherate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 78.92h， 生成 (3R,5R)-methyl 3-(benzylthio-methyl)-3-methyl-2-oxo-5-phenylmorpholine-4-carboxylate
  参考文献：
  名称：

  Stereoselective synthesis of a dialkylhydantoin featuring an asymmetric Strecker reaction on an acyclic dialkyl ketone

  摘要：

  A diastereoselective Strecker reaction using (R)-(-)-phenylglycinol forms the basis of a concise scalemic route to dialkylhydantoin 1. The phenylglycinol functionality was exploited in the manipulation of the aminonitrile Strecker product through to the dialkylhydantoin via a short, efficient sequence involving crystalline intermediates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.008

文献信息

• Stereoselective synthesis of a dialkylhydantoin featuring an asymmetric Strecker reaction on an acyclic dialkyl ketone
  作者：Neil Barnwell、Andrew Watts、Lindsay Purdie、Duncan M. Gill

  DOI：10.1016/j.tetlet.2012.02.008

  日期：2012.4

  A diastereoselective Strecker reaction using (R)-(-)-phenylglycinol forms the basis of a concise scalemic route to dialkylhydantoin 1. The phenylglycinol functionality was exploited in the manipulation of the aminonitrile Strecker product through to the dialkylhydantoin via a short, efficient sequence involving crystalline intermediates. (C) 2012 Elsevier Ltd. All rights reserved.