3-苄基-5-乙烯基-1,3-恶唑烷-2-酮 | 303767-29-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 3-苄基-5-乙烯基-1,3-恶唑烷-2-酮
• 英文名称: 3-benzyl-5-vinyl-1,3-oxazolidin-2-one
• 英文别名: 3-benzyl-5-vinyloxazolidin-2-one；3-Benzyl-5-ethenyl-1,3-oxazolidin-2-one
• CAS: 303767-29-5
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: RFXXGUDIMNZAAA-UHFFFAOYSA-N

物化性质

• 沸点：
  390.8±41.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) 、 3-苄基-5-乙烯基-1,3-恶唑烷-2-酮 以 四氢呋喃 为溶剂， 40.0 ℃ 、5.0 MPa 条件下， 反应 20.0h， 以83%的产率得到
  参考文献：
  名称：

  Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts

  摘要：

  Silver(I) carboxylate complexes promote the carboxylative cyclization of allenylmethylamines to afford 5-alkenyl-1,3-oxazolidin-2-ones in 2-propanol. The use of an N-heterocyclic carbene ligand (IPr) under pressurized CO2 is effective in suppressing the intramolecular hydroamination that leads to 2,5-dihydropyrroles. The mechanism involving a nucleophilic attack of the carbamate of the allene moiety and a subsequent protonation was realized on the basis of experimental and theoretical results involving a model intermediate, the alkenylgold(I) complex, which was synthesized from Au(OH)(IPr) and 1-methylamino-2,3-butadiene.

  DOI：

  10.1021/acs.orglett.5b00809
• 作为产物：
  描述：

  在 phosphan 、 platinum(II) chloride 、 tin(ll) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 以93%的产率得到3-苄基-5-乙烯基-1,3-恶唑烷-2-酮
  参考文献：
  名称：

  N-烯丙基氨基甲酸酯的铂催化环化合成 5-乙烯基恶唑烷酮

  摘要：

  进行氨基甲酸酯的氧亲核试剂与烯丙基溴的铂催化加成，以良好的产率提供一系列具有生物活性的 5-乙烯基取代的恶唑烷酮。在反应过程中，假设铂络合物、SnCl2 和烯丙基溴在氨基甲酸酯氧亲核试剂的存在下生成亲电烯丙基铂中间体。无论氮和氧原子上的取代如何，该方法都提供了范围广泛的 5-乙烯基恶唑烷酮。

  DOI：

  10.1002/ejoc.201101799

文献信息

• A simple and easy access to 3-N-alkyl-5-vinyloxazolidinones mediated by palladium–phosphine catalysts
  作者：Shinji Tanimori、Ushio Inaba、Yoshihiro Kato、Mitsunori Kirihata

  DOI：10.1016/s0040-4020(03)00548-9

  日期：2003.5

  A new entry for the synthesis of 3-alkyl substituted 5-vinyloxazolidin-2-one derivatives 2 from cis-2-butenylene-1,4-dicarbonate 1 and primary amines mediated by palladium–phosphine catalysts is described. The scope and limitation, a plausible mechanism, and an asymmetric version of the reaction are also discussed.

  3-烷基的合成新条目取代的5- vinyloxazolidin -2-酮衍生物2从顺-2-亚丁烯基-1,4-二碳酸酯1和通过钯膦催化剂介导的伯胺进行说明。还讨论了反应的范围和局限性，合理的机理和不对称形式。
• Palladium-catalyzed carboxylative cyclization of α-allenyl amines in dense carbon dioxide
  作者：Yoshihito Kayaki、Naoko Mori、Takao Ikariya

  DOI：10.1016/j.tetlet.2009.09.015

  日期：2009.11

  Carboxylative transformation of 2,3-allenic amines into 5-vinyl-1,3-oxazolidin-2-ones was promoted by palladium catalysts under a pressurized CO2 condition. The presence of a stereogenic center adjacent to the allene group resulted in the formation of the corresponding cyclic urethane as a single trans-diastereomer.

  在加压的CO 2条件下，钯催化剂促进了2,3-烯丙胺向5-乙烯基-1,3-恶唑烷-2-酮的羧化转化。邻近丙二烯基的立构中心的存在导致形成相应的环状氨基甲酸酯作为单一的反式非对映异构体。
• Novel palladium-catalyzed oxazolidone synthesis
  作者：Shinji Tanimori、Mitsunori Kirihata

  DOI：10.1016/s0040-4039(00)00924-2

  日期：2000.8

  Reaction of dimethyl (Z)-2-butenylene dicarbonate la with primary amines in the presence of [Pd(eta(3)- C3H5)Cl](2) and 1,1'-bis(diphenylphosphino)ferrocene (dppf) produced vinyl-oxazolidone compounds 2 in up to 70% yield. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts
  作者：Kyohei Yamashita、Shun Hase、Yoshihito Kayaki、Takao Ikariya

  DOI：10.1021/acs.orglett.5b00809

  日期：2015.5.15

  Silver(I) carboxylate complexes promote the carboxylative cyclization of allenylmethylamines to afford 5-alkenyl-1,3-oxazolidin-2-ones in 2-propanol. The use of an N-heterocyclic carbene ligand (IPr) under pressurized CO2 is effective in suppressing the intramolecular hydroamination that leads to 2,5-dihydropyrroles. The mechanism involving a nucleophilic attack of the carbamate of the allene moiety and a subsequent protonation was realized on the basis of experimental and theoretical results involving a model intermediate, the alkenylgold(I) complex, which was synthesized from Au(OH)(IPr) and 1-methylamino-2,3-butadiene.
• Platinum-Catalyzed Cyclization of N-Allyl Carbamates for the Synthesis of 5-Vinyloxazolidinones
  作者：Hyo-Sang Yoon、Ju-Hye Kim、Eun Joo Kang、Hye-Young Jang

  DOI：10.1002/ejoc.201101799

  日期：2012.4

  Platinum-catalyzed addition of the oxygen nucleophile of a carbamate to an allyl bromide was carried out to afford a range of biologically active 5-vinyl-substituted oxazolidinones in good yields. Over the course of the reaction, a platinum complex, SnCl2, and the allyl bromide are assumed to generate an electrophilic allyl-platinum intermediate in the presence of carbamate oxygen nucleophiles. This

  进行氨基甲酸酯的氧亲核试剂与烯丙基溴的铂催化加成，以良好的产率提供一系列具有生物活性的 5-乙烯基取代的恶唑烷酮。在反应过程中，假设铂络合物、SnCl2 和烯丙基溴在氨基甲酸酯氧亲核试剂的存在下生成亲电烯丙基铂中间体。无论氮和氧原子上的取代如何，该方法都提供了范围广泛的 5-乙烯基恶唑烷酮。