(4S)-(1H-indol-3-ylmethyl)-3-[(1S)-phenylethyl]-oxazolidin-2-one | 395063-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (4S)-(1H-indol-3-ylmethyl)-3-[(1S)-phenylethyl]-oxazolidin-2-one
• 英文别名: (4S)-4-(1H-indol-3-ylmethyl)-3-[(1S)-1-phenylethyl]-1,3-oxazolidin-2-one
• CAS: 395063-37-3
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: KIYLHMOMEFGEFM-YOEHRIQHSA-N

物化性质

• 沸点：
  585.0±33.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S)-(1H-indol-3-ylmethyl)-3-[(1S)-phenylethyl]-oxazolidin-2-one 在 氨 、 lithium 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到S-4-(1H-吲哚-3-甲基)-2-噁唑烷酮
  参考文献：
  名称：

  Synthesis of Substituted-(l)-Tryptophanols from an Enantiomerically Pure Aziridine-2-methanol

  摘要：

  [GRAPHICS]Enantiomerically pure (l)-tryptophanol (5) was synthesized from 4(R)-iodomethyl-2-oxazolidinone (2) and indolylmagnesium bromide in three steps (52% overall yield). Using this procedure, we also prepared various tryptophanols with substituent(s) on the indole ring. Furthermore, optically active 4(R)-iodomethyl-2-oxazolidinone was readily prepared from an enantiomerically pure aziridine-2(S)-methanol in high yield.

  DOI：

  10.1021/ol016861+
• 作为产物：
  描述：

  吲哚 、 4(R)-(iodomethyl)-3-[(1S)-phenylethyl]oxazolidin-2-one 在 乙基溴化镁 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 以62%的产率得到(4S)-(1H-indol-3-ylmethyl)-3-[(1S)-phenylethyl]-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of Substituted-(l)-Tryptophanols from an Enantiomerically Pure Aziridine-2-methanol

  摘要：

  [GRAPHICS]Enantiomerically pure (l)-tryptophanol (5) was synthesized from 4(R)-iodomethyl-2-oxazolidinone (2) and indolylmagnesium bromide in three steps (52% overall yield). Using this procedure, we also prepared various tryptophanols with substituent(s) on the indole ring. Furthermore, optically active 4(R)-iodomethyl-2-oxazolidinone was readily prepared from an enantiomerically pure aziridine-2(S)-methanol in high yield.

  DOI：

  10.1021/ol016861+

文献信息

• Synthesis of Substituted-(<i>l</i>)-Tryptophanols from an Enantiomerically Pure Aziridine-2-methanol
  作者：Do Kyu Pyun、Cheol Hae Lee、Hyun-Joon Ha、Chan Sun Park、Jae-Won Chang、Won Koo Lee

  DOI：10.1021/ol016861+

  日期：2001.12.1

  [GRAPHICS]Enantiomerically pure (l)-tryptophanol (5) was synthesized from 4(R)-iodomethyl-2-oxazolidinone (2) and indolylmagnesium bromide in three steps (52% overall yield). Using this procedure, we also prepared various tryptophanols with substituent(s) on the indole ring. Furthermore, optically active 4(R)-iodomethyl-2-oxazolidinone was readily prepared from an enantiomerically pure aziridine-2(S)-methanol in high yield.