4-methyl-3-pentyl-2-oxazolidinone

• 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: 4-methyl-3-pentyl-2-oxazolidinone
• 英文别名: 4-methyl-3-pentyl-oxazolidin-2-one；4-methyl-3-pentyl-1,3-oxazolidin-2-one
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: BKMQCRXFQNUSTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-methyl-2-oxazolidone 、 1-碘戊烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 61.0h， 以73%的产率得到4-methyl-3-pentyl-2-oxazolidinone
  参考文献：
  名称：

  [EN] CARBAMATES USEFUL AS FRAGANCES
  [FR] COMPOSES ORGANIQUES

  摘要：

  公开号：

  WO2004089880A3

文献信息

• Synthesis of Oxazolidinones and 1,2-Diamines from<i>N</i>-Alkyl Aziridines
  作者：Allan R. Pinhas、Matthew T. Hancock

  DOI：10.1055/s-2004-831174

  日期：——

  Reactions of N-alkyl-substituted aziridines with LiI followed by an electrophile are discussed. In the first series of reactions, the electrophile is carbon dioxide and the product is an oxazolidinone. In all cases, either no reaction occurred or a high yield of product was obtained. HMPA had to be added to some reactions to dramatically improve the regiochemistry. Net retention of stereochemistry was observed. In the second series of reactions, the electrophile is an iminium salt and the product is a 1,2-diamine. Here the reaction is highly regioselective in THF without the addition of HMPA. Unlike the oxazolidinone chemistry, the diamine formation works equally well with or without the addition of LiI. With respect to the regiochemistry, the results are the same with and without added LiI. However, with respect to the stereochemistry, in the presence of added LiI, the reaction with the iminium salt goes with net retention of stereochemistry. In contrast, with no added LiI, in some cases the reaction goes with net retention and in some cases with net inversion of stereochemistry.

  讨论了 N-烷基取代的氮丙啶与 LiI 以及亲电子体的反应。在第一组反应中，亲电子体是二氧化碳，产物是恶唑烷酮。在所有反应中，要么没有发生反应，要么得到的产物产量很高。有些反应必须加入 HMPA 才能显著改善区域化学性。观察到了立体化学的净保留。在第二系列反应中，亲电子体是亚胺盐，产物是 1,2-二胺。该反应在 THF 中具有高度区域选择性，无需添加 HMPA。与噁唑烷酮化学反应不同的是，无论是否添加 LiI，二胺的生成效果都一样好。在区域化学方面，添加和不添加 LiI 的结果是一样的。不过，在立体化学方面，在添加 LiI 的情况下，与亚胺盐的反应会净保留立体化学。与此相反，在不添加 LiI 的情况下，在某些情况下反应会净保留立体化学，而在某些情况下则会净反转立体化学。
• A convenient and inexpensive conversion of an aziridine to an oxazolidinone
  作者：Matthew T. Hancock、Allan R. Pinhas

  DOI：10.1016/s0040-4039(03)01325-x

  日期：2003.7

  The conversion of an aziridine to the corresponding oxazolidinone using only carbon dioxide and a catalytic amount of lithium iodide is discussed. In all cases, either no reaction occurred or a high yield of product was obtained. HMPA has been added to the reaction mixture, as needed, to drastically improve the regioselectivity. Net retention of stereochemistry between the starting aziridine and the

  讨论了仅使用二氧化碳和催化量的碘化锂将氮丙啶转化为相应的恶唑烷酮。在所有情况下，要么没有反应发生，要么获得高产率的产物。HMPA已根据需要添加到反应混合物中，以大大提高区域选择性。观察到起始氮丙啶和产物恶唑烷酮之间的立体化学净保留。
• Organic compounds
  申请人：Flachsmann Felix

  公开号：US20060270588A1

  公开（公告）日：2006-11-30

  Tertiary non-vinylic carbamates of molecular weight less than 350 are useful as fragrance ingredients. A method of preparation is also described.

  分子量小于350的第三级非乙烯基碳酸酯可用作香料成分。还描述了一种制备方法。
• Microwave assisted synthesis of fragrant jasmone heterocyclic analogues
  作者：Anna Pawełczyk、Lucjusz Zaprutko

  DOI：10.1016/j.ejmech.2005.09.012

  日期：2006.5

  cis-Jasmone, from jasmonoid group, is an important jasmine odor fragrance compound. The syntheses of new heterocyclic analogues of jasmone were described. Five analogues of this compound were prepared under microwave irradiation and the results of the microwave assisted syntheses were compared with classical, thermally initiated reactions in solvent. Microwave reactions were carried out successfully, and reaction times were significantly reduced to a few minutes. Three of five obtained analogues, pyrrolidinone, oxazolidinone and thiazolidinone demonstrated an interesting, specific odor which was compared with floral, typical jasmine odor of jasmone. (c) 2006 Elsevier SAS. All rights reserved.
• EP1613587A2
  申请人：——

  公开号：EP1613587A2

  公开（公告）日：2006-01-11