1,5,6,10b-tetrahydro-2H-isoquino[2,1-b][1,2]oxazol-2-one | 33934-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,5,6,10b-tetrahydro-2H-isoquino[2,1-b][1,2]oxazol-2-one
• 英文别名: (3R,4’S)-2-N-benzyl-3-(2’,2’-dimethyl-1',3’-dioxolan-4’-yl)-1,2-isoxazolidin-5-one；1,5,6,10b-tetrahydro-isoxazolo[3,2-a]isoquinolin-2-one；1,5,6,10b-Tetrahydro-[1,2]oxazolo[3,2-a]isoquinolin-2-one
• CAS: 33934-42-8
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: UYZVMXLXDCMZKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (三甲基硅基)乙酸乙酯 、 异喹啉-N-氧化物 生成 1,5,6,10b-tetrahydro-2H-isoquino[2,1-b][1,2]oxazol-2-one
  参考文献：
  名称：

  TSUGE, OTOHIKO;SONE, KAZUHIRO;URANO, SATOSHI;MATSUDA, KOYO, J. ORG. CHEM., 1982, 47, N 26, 5171-5177

  摘要：

  DOI：

文献信息

• Thiourea-catalyzed nucleophilic addition of TMSCN and ketene silyl acetals to nitrones and aldehydes
  作者：Tomotaka Okino、Yasutaka Hoashi、Yoshiji Takemoto

  DOI：10.1016/s0040-4039(03)00433-7

  日期：2003.3

  The effect of hydrogen bonding between nitrones and urea derivatives in the nucleophilic addition reaction was examined. Thioureas bearing an electron-withdrawing group on an aromatic ring, behave like Lewis acid to promote the addition of TMSCN and ketene silyl acatals to various nitrones and aldehydes. Presumed interaction between nitrones and thioureas was supported by NMR experiments.

  研究了亲核加成反应中硝酮与脲衍生物之间氢键的影响。在芳香环上带有吸电子基团的硫脲的行为像路易斯酸，以促进TMSCN和烯酮甲硅烷基的缩醛向各种硝酮和醛的加成。NMR实验支持了硝酮与硫脲之间的假定相互作用。
• Direct Synthesis of<b><i>N</i></b>-Hydroxy<b><i>β</i></b>-Amino Acid Esters from Carboxylic Esters and Nitrones
  作者：Kazuhiro Kobayashi、Takeshi Matoba、Susumu Irisawa、Atsushi Takanohashi、Miyuki Tanmatsu、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1246/bcsj.73.2805

  日期：2000.12

  The direct synthesis of the title amino acid derivatives from carboxylic esters and nitrones can be achieved in fair to good yields when lithium or magnesium ester enolates were treated with nitrones in THF at -78 °C or in Et2O at -20 to 0 °C, respectively. The products from the reaction of t-butyl acetate with 3,4-dihydroisoquinoline N-oxide or 5,5-dimethylpyrroline 1-oxide were transformed into (1

  当锂或镁酯烯醇化物在 THF 中在 -78 °C 或在 Et2O 中在 -20 到 0 °C 下用硝酮处理时，从羧酸酯和硝酮直接合成标题氨基酸衍生物可以达到相当到良好的产率，分别。乙酸叔丁酯与 3,4-二氢异喹啉 N-氧化物或 5,5-二甲基吡咯啉 1-氧化物反应的产物转化为 (1,2,3,4-四氢异喹啉-1-亚基) 乙酸酯或 (吡咯烷-2-亚基）乙酸酯衍生物在三苯基膦、四氯化碳和三乙胺的存在下，在回流的二氯甲烷中。
• REACTIONS OF SILYL-SUBSTITUTED CARBANIONS WITH NITRONES
  作者：Otohiko Tsuge、Kazuhiro Sone、Satoshi Urano

  DOI：10.1246/cl.1980.977

  日期：1980.8.5

  The reaction of carbanions, prepared from 2-(trimethylsilylmethyl)pyridine or N,N-dimethyltrimethylsilylacetamide and lithium diisopropylamide in tetrahydrofuran, with α-aryl-N-phenylnitrones afforded a mixture of the corresponding (E)-alkene, azobenzene and azoxybenzene, respectively. On the other hand, the carbanions reacted with cyclic nitrones to give the corresponding aziridine and/or hydroxylamine

  由 2-(三甲基甲硅烷基甲基)吡啶或 N,N-二甲基三甲基甲硅烷基乙酰胺和二异丙基氨基锂在四氢呋喃中制备的碳负离子与 α-芳基-N-苯基硝酮反应，分别得到相应的 (E)-烯烃、偶氮苯和偶氮苯的混合物. 另一方面，碳负离子与环状硝酮反应得到相应的氮丙啶和/或羟胺衍生物作为主要产物。
• Organocatalyzed Synthesis of Isoxazolidin-5-ones: The Meldrum’s Acid Approach
  作者：Svetlana Postikova、Tony Tite、Vincent Levacher、Jean-François Brière

  DOI：10.1002/adsc.201300465

  日期：2013.9.16

  Meldrum’s acid has turned out to be a useful ketene equivalent when faced to nitrone dipoles to form various isoxazolidin‐5‐one derivatives under very mild Brønsted base organocatalytic conditions. The first asymmetric version of this original domino anionic formal [3+2] cycloaddition–decarboxylation reaction was demonstrated by means of quinine‐based organocatalysts.

  当在非常温和的布朗斯台德碱有机催化条件下，面对硝酮偶极子形成各种异恶唑烷5-5衍生物时，Meldrum的酸已被证明是有用的乙烯酮当量。最初的多米诺胺阴离子形式的[3 + 2]环加成-脱羧反应的第一个不对称形式是通过奎宁为基础的有机催化剂证明的。
• Reactions of lithio trimethylsilyl compounds with nitrones
  作者：Otohiko Tsuge、Kazunori Sone、Satoshi Urano、Koyo Matsuda

  DOI：10.1021/jo00147a026

  日期：1982.12