(1R,4S)-2-[(1'S,4'R)-2-oxo-1-bornylcarbonyl]-2-aza-3-oxabicyclo[2.2.2]-5-octene | 459124-77-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,4S)-2-[(1'S,4'R)-2-oxo-1-bornylcarbonyl]-2-aza-3-oxabicyclo[2.2.2]-5-octene
• 英文别名: (1S,4R)-7,7-dimethyl-1-[(1S,4R)-2-oxa-3-azabicyclo[2.2.2]oct-5-ene-3-carbonyl]bicyclo[2.2.1]heptan-2-one
• CAS: 459124-77-7
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: NPBHULWSOFUQSP-JBBSTSQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4S)-2-[(1'S,4'R)-2-oxo-1-bornylcarbonyl]-2-aza-3-oxabicyclo[2.2.2]-5-octene 在 lithium aluminium tetrahydride 、 盐酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 5.0h， 以91%的产率得到2-Oxa-3-azabicyclo<2.2.2>oct-5-ene hydrochloride
  参考文献：
  名称：

  Switch in asymmetric induction sense in cycloadditions using camphor-based nitroso dienophiles

  摘要：

  We have observed a unique reversal in the absolute stereochemistry of the principal adducts from the cycloadditions of camphor-based acylnitroso dienophiles as compared to the adducts obtained through reactions of the corresponding camphor-based chloronitroso compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00192-1
• 作为产物：
  描述：

  (S)-(+)-酮基蒎酸 在 氯化亚砜 、 tetraethylammonium metaperiodate 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 (1R,4S)-2-[(1'S,4'R)-2-oxo-1-bornylcarbonyl]-2-aza-3-oxabicyclo[2.2.2]-5-octene
  参考文献：
  名称：

  Switch in asymmetric induction sense in cycloadditions using camphor-based nitroso dienophiles

  摘要：

  We have observed a unique reversal in the absolute stereochemistry of the principal adducts from the cycloadditions of camphor-based acylnitroso dienophiles as compared to the adducts obtained through reactions of the corresponding camphor-based chloronitroso compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00192-1

文献信息

• Switch in asymmetric induction sense in cycloadditions using camphor-based nitroso dienophiles
  作者：Ying-Chuan Wang、Tzung-Min Lu、Shanmugham Elango、Chao-Kuo Lin、Chia-Tzung Tsai、Tu-Hsin Yan

  DOI：10.1016/s0957-4166(02)00192-1

  日期：2002.5

  We have observed a unique reversal in the absolute stereochemistry of the principal adducts from the cycloadditions of camphor-based acylnitroso dienophiles as compared to the adducts obtained through reactions of the corresponding camphor-based chloronitroso compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.