(1S,4R)-N-羟基-7,7-二甲基-2-氧代双环[2.2.1]庚烷-1-甲酰胺 | 459124-75-5

• 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
• 中文名称: (1S,4R)-N-羟基-7,7-二甲基-2-氧代双环[2.2.1]庚烷-1-甲酰胺
• 英文名称: (1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid hydroxyamide
• 英文别名: (1S,4R)-N-hydroxy-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxamide
• CAS: 459124-75-5
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: JVJGVVLLVCSDOM-LDWIPMOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,4R)-N-羟基-7,7-二甲基-2-氧代双环[2.2.1]庚烷-1-甲酰胺 在 lithium aluminium tetrahydride 、 氯化亚砜 、 jones reagent 、 tetraethylammonium metaperiodate 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 18.0h， 生成 ketopinic acid chloride
  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 、 三甲基氯硅烷 、 盐酸羟胺 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以96%的产率得到(1S,4R)-N-羟基-7,7-二甲基-2-氧代双环[2.2.1]庚烷-1-甲酰胺
  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

• Syntheses of Optically Pure Conduramines via the Strategy of Hetero Diels−Alder Reaction of Masked <i>o</i>-Benzoquinones with Homochiral Nitroso Dienophiles
  作者：Ping-Hsun Lu、Ching-Shun Yang、Badugu Devendar、Chun-Chen Liao

  DOI：10.1021/ol100840n

  日期：2010.6.4

  Highly stereoselective hetero Diels−Alder reactions of masked o-benzoquinones (MOBs) with homochiral nitroso dienophiles are described along with their application in the syntheses of (+)-ent-conduramine F-1, (+)-conduramine E-1, (−)-conduramine A-1, (+)-conduramine A-1 tetraacetate, and (−)-ent-conduramine A-1 tetraacetate.

  描述了被掩盖的邻苯甲醌（MOB）与同手性亚硝基二烯亲和体的高度立体选择性杂Diels-Alder反应及其在（+）- ent -conduramine F-1，（+）-conduramine E-1，（ -）-conduramine A-1，（+）-conduramine A-1四乙酸盐和（-）- ent -conduramine A-1四乙酸盐。
• 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.