3-((2E)-octenoyl)-2-oxazolidinone | 192379-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-((2E)-octenoyl)-2-oxazolidinone
• 英文别名: 3-[(E)-oct-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 192379-69-4
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: CWKJMKYKGDVHMD-VOTSOKGWSA-N

物化性质

• 沸点：
  287.7±23.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  环戊二烯 、 3-((2E)-octenoyl)-2-oxazolidinone 在 GO*Cu(OTf)2 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以84%的产率得到3-[(3'-pentylbicyclo[2.2.1]hept-5'-en-2'-yl)carbonyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Dendritic Bis(oxazoline)copper(II) Catalysts. 2.¹ Synthesis, Reactivity, and Substrate Selectivity

  摘要：

  A series of dendritic bis(oxazoline) Ligands 1-4 were synthesized to evaluate the effects of the degree of branching of a dendritic sector on both the reactivity and selectivity of their corresponding copper(II) complex-catalyzed Diels-Alder reaction between cyclopentadiene and a crotonyl imide. Kinetic studies unveiled a two-step mechanism of the Diels-Alder reaction, in which a reversible binding of the dienophile to the copper complex was followed by a rate-determining reaction between the resulting dienophile-catalyst complex with the diene. Furthermore, two interesting features emerged: first, the formation constant of the dienophile-catalyst complex decreased gradually on going from the lower to higher generations, and secondly, while the Diels-Alder reaction rate constant remained essentially the same from the zeroth to second generation catalysts, it dropped abruptly for the third generation one. These observations were rationalized as a consequence of a folding-back of the dendritic sectors toward the catalytic unit at the third generation, so that increase in steric size impeded both the reactivity and binding profiles of the catalytic system. This behavior was reminiscent of related phenomena observed by others from solvatomatic, photophysical, and viscosity studies. In line with this reasoning, a slight but noticeable substrate selectivity was observed for the third generation catalyst, which was absence for the lower ones, in competitive kinetic studies involving two dienophiles of different steric sizes.

  DOI：

  10.1021/jo970383s
• 作为产物：
  描述：

  octanoyl 2-oxazolidinone amide 在 正丁基锂 、 N-叔丁基苯硫腈氯化物 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以90%的产率得到3-((2E)-octenoyl)-2-oxazolidinone
  参考文献：
  名称：

  在温和条件下将羧酸衍生物一锅式脱氢为α，β-不饱和羰基化合物

  摘要：

  仅通过处理它们的烯醇锂，即可在-78°C下以锅法将N-酰基-2-恶唑烷酮，δ-内酯和δ-内酰胺等羧酸衍生物平稳脱氢为相应的α，β-不饱和羰基化合物。与ñ -叔-butylbenzenesulfinimidoyl酰氯。

  DOI：

  10.1016/j.tetlet.2004.11.106

文献信息

• A Two-Carbon Homologation of Aldehydes and Ketones Using Ynamides
  作者：Richard Hsung、Lingfeng You、Ziyad Al-Rashid、Ruth Figueroa、Sunil Ghosh、Gang Li、Ting Lu

  DOI：10.1055/s-2007-984513

  日期：2007.7

  Reactions of ynamides with Lewis acid activated -aldehydes, enals, or ketones in the formation of acrylic amides are described here. The overall process is an equivalent of a two-carbon homologation of aldehydes or ketones and is selective for the E-isomer.

  在此描述了炔酰胺与路易斯酸活化的醛、烯醛或酮在丙烯酰胺形成中的反应。整个过程相当于醛或酮的双碳同系化，并且对 E 异构体具有选择性。
• Construction of a new asymmetric reaction site: asymmetric 1,4-addition of thiol using pentagonal bipyramidal Hf(salen) complex as catalyst
  作者：Kazuhiro Matsumoto、Akira Watanabe、Tatsuya Uchida、Kayoko Ogi、Tsutomu Katsuki

  DOI：10.1016/j.tetlet.2004.01.095

  日期：2004.3

  Pentagonal bipyramidal Hf(salen) complex I was found to serve as a catalyst for 1,4-addition reaction of thiol to N-(2alkenoyl)-2-oxazolidinones. (C) 2004 Elsevier Ltd. All rights reserved.
• One-pot dehydrogenation of carboxylic acid derivatives to α,β-unsaturated carbonyl compounds under mild conditions
  作者：Jun-ichi Matsuo、Yayoi Aizawa

  DOI：10.1016/j.tetlet.2004.11.106

  日期：2005.1

  Carboxylic acid derivatives such as N-acyl-2-oxazolidones, δ-lactones, and δ-lactams were smoothly dehydrogenated to the corresponding α,β-unsaturated carbonyl compounds in one-pot manner at −78 °C just by treating their lithium enolates with N-tert-butylbenzenesulfinimidoyl chloride.

  仅通过处理它们的烯醇锂，即可在-78°C下以锅法将N-酰基-2-恶唑烷酮，δ-内酯和δ-内酰胺等羧酸衍生物平稳脱氢为相应的α，β-不饱和羰基化合物。与ñ -叔-butylbenzenesulfinimidoyl酰氯。
• Dendritic Bis(oxazoline)copper(II) Catalysts. 2.¹ Synthesis, Reactivity, and Substrate Selectivity
  作者：Hak-Fun Chow、Chi Ching Mak

  DOI：10.1021/jo970383s

  日期：1997.7.1

  A series of dendritic bis(oxazoline) Ligands 1-4 were synthesized to evaluate the effects of the degree of branching of a dendritic sector on both the reactivity and selectivity of their corresponding copper(II) complex-catalyzed Diels-Alder reaction between cyclopentadiene and a crotonyl imide. Kinetic studies unveiled a two-step mechanism of the Diels-Alder reaction, in which a reversible binding of the dienophile to the copper complex was followed by a rate-determining reaction between the resulting dienophile-catalyst complex with the diene. Furthermore, two interesting features emerged: first, the formation constant of the dienophile-catalyst complex decreased gradually on going from the lower to higher generations, and secondly, while the Diels-Alder reaction rate constant remained essentially the same from the zeroth to second generation catalysts, it dropped abruptly for the third generation one. These observations were rationalized as a consequence of a folding-back of the dendritic sectors toward the catalytic unit at the third generation, so that increase in steric size impeded both the reactivity and binding profiles of the catalytic system. This behavior was reminiscent of related phenomena observed by others from solvatomatic, photophysical, and viscosity studies. In line with this reasoning, a slight but noticeable substrate selectivity was observed for the third generation catalyst, which was absence for the lower ones, in competitive kinetic studies involving two dienophiles of different steric sizes.