(R)-N-Hydroxy-N-(1-benz[b]thien-2-yl-ethyl)amine | 162750-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (R)-N-Hydroxy-N-(1-benz[b]thien-2-yl-ethyl)amine
• 英文别名: N-[(1R)-1-(1-benzothiophen-2-yl)ethyl]hydroxylamine
• CAS: 162750-04-1
• 化学式: C₁₀H₁₁NOS
• 分子量: 193.269
• InChiKey: YPKATNMCYFSXKB-SSDOTTSWSA-N

物化性质

• 沸点：
  366.8±44.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  60.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三甲基硅基异氰酸酯 、 (R)-N-Hydroxy-N-(1-benz[b]thien-2-yl-ethyl)amine 以 四氢呋喃 为溶剂， 以72%的产率得到1-[(1R)-1-(1-苯并噻吩-2-基)乙基]-1-羟基脲
  参考文献：
  名称：

  Enantioselective synthesis of 5-LO inhibitors using a gulofuranose auxiliary

  摘要：

  The pure R-(+)-enantiomer of 5-lipoxygenase inhibitor Zileuton was prepared by diastereoselective methyl Grignard addition to an aldonitrone bearing a D-gulofuranose-derived chiral auxiliary. Addition of the Lewis acid trimethylaluminum leads to a reversal of the alkylation stereochemistry and the potent pyrido analogue, R-(+)-RS-27871 was prepared in this way from an L-gulofuranose-derived nitrone.

  DOI：

  10.1016/s0040-4039(00)79952-7
• 作为产物：
  描述：

  苯并噻吩 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 13.0h， 生成 (R)-N-Hydroxy-N-(1-benz[b]thien-2-yl-ethyl)amine
  参考文献：
  名称：

  Enantioselective synthesis of 5-LO inhibitors using a gulofuranose auxiliary

  摘要：

  The pure R-(+)-enantiomer of 5-lipoxygenase inhibitor Zileuton was prepared by diastereoselective methyl Grignard addition to an aldonitrone bearing a D-gulofuranose-derived chiral auxiliary. Addition of the Lewis acid trimethylaluminum leads to a reversal of the alkylation stereochemistry and the potent pyrido analogue, R-(+)-RS-27871 was prepared in this way from an L-gulofuranose-derived nitrone.

  DOI：

  10.1016/s0040-4039(00)79952-7

文献信息

• Addition of Organometallic Reagents to N-Glycosyl Nitrones. Enantioselective Syntheses of (+)-(R)- and (-)-(S)-Zileuton
  作者：Anwer Basha、Rodger Henry、Maureen A. McLaughlin、James D. Ratajczyk、Steven J. Wittenberger

  DOI：10.1021/jo00099a052

  日期：1994.10
• US5663368A
  申请人：——

  公开号：US5663368A

  公开（公告）日：1997-09-02
• Enantioselective synthesis of 5-LO inhibitors using a gulofuranose auxiliary
  作者：John C. Rohloff、Thomas V. Alfredson、Martin A. Schwartz

  DOI：10.1016/s0040-4039(00)79952-7

  日期：1994.2

  The pure R-(+)-enantiomer of 5-lipoxygenase inhibitor Zileuton was prepared by diastereoselective methyl Grignard addition to an aldonitrone bearing a D-gulofuranose-derived chiral auxiliary. Addition of the Lewis acid trimethylaluminum leads to a reversal of the alkylation stereochemistry and the potent pyrido analogue, R-(+)-RS-27871 was prepared in this way from an L-gulofuranose-derived nitrone.