(S)-4-isopropyl-3-[(R)-3-methyl-4-nitrobutanoyl]-5,5-diphenyloxazolidin-2-one | 259857-38-0

• 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: (S)-4-isopropyl-3-[(R)-3-methyl-4-nitrobutanoyl]-5,5-diphenyloxazolidin-2-one
• 英文别名: (4S)-3-[(3R)-3-methyl-4-nitrobutanoyl]-5,5-diphenyl-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 259857-38-0
• 化学式: C₂₃H₂₆N₂O₅
• 分子量: 410.47
• InChiKey: LZJDUENPRUIKOJ-UTKZUKDTSA-N

物化性质

• 沸点：
  579.8±50.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-isopropyl-3-[(R)-3-methyl-4-nitrobutanoyl]-5,5-diphenyloxazolidin-2-one 在 镍 4-二甲氨基吡啶 、 lithium hydroxide 、 水 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 21.0h， 生成 N-BOC-4-氨基-3-甲基-丁酸
  参考文献：
  名称：

  Enantioselective Preparation of γ ‐Amino Acids and γ ‐Lactams from Nitro Olefins and Carboxylic Acids, with the Valine‐Derived 4‐Isopropyl‐5,5‐diphenyl‐1,3‐oxazolidin‐2‐one as an Auxiliary

  摘要：

  DOI：

  10.1002/(sici)1522-2675(19991215)82:12<2365::aid-hlca2365>3.0.co;2-#
• 作为产物：
  描述：

  (1E)-1-硝基-1-丙烯 、 (S)-3-acetyl-4-isopropyl-5,5-diphenyloxazolidin-2-one 在 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到(S)-4-isopropyl-3-[(R)-3-methyl-4-nitrobutanoyl]-5,5-diphenyloxazolidin-2-one
  参考文献：
  名称：

  Intermediates in the synthesis of nitrogen heterocycles: addition of acylated camphorsultams to nitroalkenes

  摘要：

  Reaction of acylated camphorsultam 7 with nitroalkenes in the presence of TiCl4 and Et3N gave addition products in good yields (>70%) and with excellent stereocontrol. Addition of propionylated camphorsultarn 15 to nitrostyrene gave the addition product 16 in which two new asymmetric centres were created, the stereochemical outcome of the reaction was confirmed by X-ray cystallography. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.029

文献信息

• Enantioselective Preparation of <i>γ</i> ‐Amino Acids and <i>γ</i> ‐Lactams from Nitro Olefins and Carboxylic Acids, with the Valine‐Derived 4‐Isopropyl‐5,5‐diphenyl‐1,3‐oxazolidin‐2‐one as an Auxiliary
  作者：Meinrad Brenner、Dieter Seebach

  DOI：10.1002/(sici)1522-2675(19991215)82:12<2365::aid-hlca2365>3.0.co;2-#

  日期：1999.12.15
• Intermediates in the synthesis of nitrogen heterocycles: addition of acylated camphorsultams to nitroalkenes
  作者：Joanna E. Clare、Christine L. Willis、Josephine Yuen、Kenneth W.M. Lawrie、Jonathan P.H. Charmant、Anob Kantacha

  DOI：10.1016/j.tetlet.2003.09.029

  日期：2003.10

  Reaction of acylated camphorsultam 7 with nitroalkenes in the presence of TiCl4 and Et3N gave addition products in good yields (>70%) and with excellent stereocontrol. Addition of propionylated camphorsultarn 15 to nitrostyrene gave the addition product 16 in which two new asymmetric centres were created, the stereochemical outcome of the reaction was confirmed by X-ray cystallography. (C) 2003 Elsevier Ltd. All rights reserved.