(1S,2R,6S,7R)-3-氧杂-5-氮杂三环[5.2.1.02,6]癸-8-烯-4-酮 | 139240-75-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 中文名称: (1S,2R,6S,7R)-3-氧杂-5-氮杂三环[5.2.1.02,6]癸-8-烯-4-酮
• 中文别名: 1-(2-羟基丙基)-1-亚硝基脲
• 英文名称: (+)-(1S,2R,6S,7R)-3-oxa-5-azatricyclo[5.2.1.0^2,6]dec-8-en-4-one
• 英文别名: (1S,2R,6S,7R)-3-oxa-5-azatricyclo[5.2.1.02,6]dec-8-en-4-one
• CAS: 139240-75-8
• 化学式: C₈H₉NO₂
• 分子量: 151.165
• InChiKey: GTSVZYGBBLQSTN-BNHYGAARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R,6S,7R)-3-氧杂-5-氮杂三环[5.2.1.02,6]癸-8-烯-4-酮 在 4-二甲氨基吡啶 、 正丁基锂 、 偶氮二异丁腈 、 碘 、 三正丁基氢锡 、 sodium hydride 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 21.17h， 生成 (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-3-methyl-heptanoyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one
  参考文献：
  名称：

  Sterically constrained tricyclic 2-oxazolidinone as excellent chiral auxiliary

  摘要：

  A new class of conformationally rigid 2-oxazolidinones with effectively bulky substituents, derived from the [4+2] cycloadduct of cyclopentadiene and 2-oxazolone, serve as extremely powerful chiral auxiliaries for asymmetric alkylations, Diels-Alder reactions and conjugate addition reactions. (C) 1997, Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(96)02402-1
• 作为产物：
  描述：

  (1S,2R,6S,7R)-5-((1S,2R,4R)-2-Methoxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carbonyl)-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-8-en-4-one 在 甲醇 、 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以84%的产率得到(1S,2R,6S,7R)-3-氧杂-5-氮杂三环[5.2.1.02,6]癸-8-烯-4-酮
  参考文献：
  名称：

  Chiral electrophilic “glycinal” equivalents. New synthons for optically active α-amino acids and 4-substituted 2-oxazolidinones

  摘要：

  The thermal reaction of 3-[(IS)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones (21a-c) with dialkyl azodicarboxylates (9) results in exclusive formation of [4 + 2] type cycloadducts (22 and 23) with moderate levels of diastereofacial selection (up to 72% d.e.). The diastereomers thus obtained were readily purified and subsequent treatment with acidic methanol followed by removal of the auxiliary with LiBH4/MeOH (1:2) gave optically pure 4-methoxy-5-hydrazino-2-oxazolidinones (26 and 27), which serve as alpha-aminoaldehyde templates useful for the synthesis of a wide variety of optically active alpha-amino acids as well as 4-alkyl and 4-aryl-2-oxazolidinones. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01077-0

文献信息

• Diastereoselective [4+3] Cycloadditions of Enantiopure Nitrogen-Stabilized Oxyallyl Cations
  作者：David I. MaGee、Edouard Godineau、Paul D. Thornton、Michael A. Walters、Deborah J. Sponholtz

  DOI：10.1002/ejoc.200600226

  日期：2006.8

  Diastereoselective trapping of chiral enantiopure oxyallyl cations by common dienes is reported. Excellent diastereoselectivities were obtained and depending on which auxiliary was used cycloadditions proceeded through a chelated or non-chelated pathway. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  报道了普通二烯对手性对映体纯氧烯丙基阳离子的非对映选择性捕获。获得了优异的非对映选择性，并且取决于使用的助剂，环加成通过螯合或非螯合途径进行。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Scholz,K.-H. et al., Justus Liebigs Annalen der Chemie, 1977, p. 2027 - 2035
  作者：Scholz,K.-H. et al.

  DOI：——

  日期：——
• Conformationally rigid chiral [4+2]cycloadduct-based 2-oxazolidinones as new auxiliaries
  作者：Hirofumi Matsunaga、Koreichi Kimura、Tadao Ishizuka、Mamoru Karatake、Takehisa Kunieda

  DOI：10.1016/0040-4039(91)80573-o

  日期：1991.12

  Newly introduced enantiomerically pure [4 + 2]cycloadduct-based 2-oxazolidinones which are conformationally fixed by bicyclo[2.2.2] and [2.2.1] ring systems, serve well as exellent chiral auxiliaries in the Evans' asymmetric strategy.