(+/-)-5-Methyl-4-oxa-1-azabicyclo<3.3.0>octan-8-one | 136749-84-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (+/-)-5-Methyl-4-oxa-1-azabicyclo<3.3.0>octan-8-one
• 英文别名: 7a-Methyl-2,3,6,7-tetrahydropyrrolo[2,1-b][1,3]oxazol-5-one
• CAS: 136749-84-3
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: SPSXZGPROALKAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-5-Methyl-4-oxa-1-azabicyclo<3.3.0>octan-8-one 在 吡啶 、 lithium perchlorate 作用下， 以 乙醚 为溶剂， 生成 {2-Methyl-5-oxo-1-[2-(toluene-4-sulfonyloxy)-ethyl]-pyrrolidin-2-yl}-acetic acid methyl ester
  参考文献：
  名称：

  Bridgehead-methyl analog of SC-53116 as a 5-HT4 agonist

  摘要：

  Pyrrolizidine benzamide (+/-)-2, the bridgehead-methyl analog of SC-53116, was prepared and evaluated for 5-HT4 agonism activity in the rat tunica muscularis (TMM) mucosae assay. Compound (+/-)-2 has an EC50 of 449 nM in the TMM assay, as compared to 23 nM for SC-53116, and 66 nM for the racemate of SC-53116. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.021
• 作为产物：
  描述：

  5-methoxy-5-methyl-2H-furan-2-ol 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (+/-)-5-Methyl-4-oxa-1-azabicyclo<3.3.0>octan-8-one
  参考文献：
  名称：

  呋喃对迈耶斯双环内酰胺的多功能合成：单重态氧引发的反应级联

  摘要：

  所有在一个：迈尔斯双环的内酰胺以高收率合成从使用涉及一锅单线-氧-引发的反应级联中的新的和有效的方法呋喃（参见方案; TFA =三氟乙酸）。该方法具有由于容易获得了广泛范围呋喃与各种取代基中的广泛的合成潜力。

  DOI：

  10.1002/anie.201204419

文献信息

• Synthesis of 1,4-Diketones by Reaction of Bicyclic Lactams Derived from 4-Oxoalkanoic Acids with Organolithium Compounds
  作者：Christine Wedler、Hans Schick

  DOI：10.1055/s-1992-26159

  日期：——

  Bicyclic lactams obtained from ethyl 4-oxoalkanoates and 2-aminoethanol add saturated and unsaturated aliphatic lithium compounds forming the corresponding 1,4-diketones in 41-61% yield after acidic hydrolysis.

  从 4-氧代烷酸乙酯和 2-氨基乙醇中获得的双环内酰胺加入饱和和不饱和脂肪族锂化合物，在酸性水解后形成相应的 1,4-二酮，产率为 41-61%。
• Single and Double Diastereoselection in Azomethine Ylide Cycloaddition Reactions with Unsaturated Chiral Bicyclic Lactams
  作者：Andrew H. Fray、A. I. Meyers

  DOI：10.1021/jo9600870

  日期：1996.1.1

  Double diastereoselectivity data were analyzed to provide insight into the structural features that influence pi-facial selectivity in 1,3-dipolar cycloadditions of chiral and achiral azomethine ylides to chiral, unsaturated bicyclic lactams. Three major steric contributions to the differences in stability (Delta Delta G(double dagger)) between competing cycloaddition transition states were identified. The first major set of steric interactions involve that between the dipoles and the substituents on the left hemisphere (R(2)) and concave faces of the bicyclic lactams. This effectively hindered both alpha- and beta-approaches in the nonextended transition states shown in Figure 1. The second major steric interaction was provided by the nonbonded interactions (i) between the R(1) angular substituent on the bicyclic lactam and the pi-system of the dipole as shown in Figures 3 and 4. This interaction was shown to be very significant, causing reversal in pi-facial attack of chiral and achiral dipoles when the angular substituent is changed from phenyl or methyl to hydrogen. The high diastereoselectivity observed now opens a route to highly substituted chiral, nonracemic pyrrolidines.
• Vainiotalo, Pirjo; Savolainen, Pirjo-Liisa; Ahlgren, Markku, Journal of the Chemical Society. Perkin transactions II, 1991, # 5, p. 735 - 741
  作者：Vainiotalo, Pirjo、Savolainen, Pirjo-Liisa、Ahlgren, Markku、Maelkoenen, Pentti J.、Vepsaelaeinen, Jouko

  DOI：——

  日期：——
• Wedler, Christine; Schick, Hans; Scharfenberg-Pfeiffer, Doris, Liebigs Annalen der Chemie, 1992, # 1, p. 29 - 32
  作者：Wedler, Christine、Schick, Hans、Scharfenberg-Pfeiffer, Doris、Reck, Guenter

  DOI：——

  日期：——
• A Versatile Synthesis of Meyers’ Bicyclic Lactams from Furans: Singlet-Oxygen-Initiated Reaction Cascade
  作者：Dimitris Kalaitzakis、Tamsyn Montagnon、Ioanna Alexopoulou、Georgios Vassilikogiannakis

  DOI：10.1002/anie.201204419

  日期：2012.8.27

  All in one: Meyers' bicyclic lactams were synthesized in high yield from furans using a new and powerful method that involves a one‐pot singlet‐oxygen‐initiated reaction cascade (see scheme; TFA=trifluoroacetic acid). This method has broad synthetic potential because of the ease of access to a wide range of furans with a variety of substituents.

  所有在一个：迈尔斯双环的内酰胺以高收率合成从使用涉及一锅单线-氧-引发的反应级联中的新的和有效的方法呋喃（参见方案; TFA =三氟乙酸）。该方法具有由于容易获得了广泛范围呋喃与各种取代基中的广泛的合成潜力。

表征谱图