(1S)-7,7-dimethyl-2-oximino-bicyclo<2.2.1>heptane-1-carboxylic acid methyl ester | 226557-11-5

• 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
• 英文名称: (1S)-7,7-dimethyl-2-oximino-bicyclo<2.2.1>heptane-1-carboxylic acid methyl ester
• CAS: 226557-11-5
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: KLDSAUNTGCBVAR-HQJQHLMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  58.89
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S)-7,7-dimethyl-2-oximino-bicyclo<2.2.1>heptane-1-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (1S,2R)-1-(hydroxymethyl)-2-amino-7,7-dimethyl-bicyclo<2.2.1>heptane
  参考文献：
  名称：

  New 1,3-amino alcohols derived from ketopinic acid and their application in catalytic enantioselective reduction of prochiral ketones

  摘要：

  New 1,3-amino alcohols, (1S,2S)- and (1S,2R)-1-hydroxylmethyl-2-amino-7,7-dimethyl bicyclo[2,2,1]heptane (endo-4 and exo-4), were prepared from ketopinic acid via oximation and reduction. The enantioselective borane reduction of prochiral ketones catalyzed by the borane complex of exo-4 was examined. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00043-9
• 作为产物：
  描述：

  ketopinic acid methyl ester 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 45.0h， 生成 (1S)-7,7-dimethyl-2-oximino-bicyclo<2.2.1>heptane-1-carboxylic acid methyl ester
  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

• Preparation and conversion of chiral O-isopropylidene-protected 4-aminocyclohexenol to various key intermediates toward narcissus alkaloids
  作者：Shanmugham Elango、Ying-Chuan Wang、Chien-Liang Cheng、Tu-Hsin Yan

  DOI：10.1016/s0040-4039(02)00543-9

  日期：2002.5

  Enantiomerically pure 4-amino-5,6-O-isopropylidenedioxycyclohex-2-en-1-ol, conveniently prepared by the union of O-isopropylidenedioxycyclohexadiene with camphor-based chloronitroso ester, was employed in the synthesis of versatile key intermediates toward narcissus alkaloids. (C) 2002 Elsevier Science Ltd. All rights reserved.