D,L-2-Methyl-4,5-cis-cyclohexanooxazoline | 1189381-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: D,L-2-Methyl-4,5-cis-cyclohexanooxazoline
• 英文别名: 2-methyl-3a,4,5,6,7,7a-hexahydro-benzooxazole；(3aR,7aS)-2-methyl-3a,4,5,6,7,7a-hexahydro-1,3-benzoxazole
• CAS: 1189381-11-0
• 化学式: C₈H₁₃NO
• 分子量: 139.197
• InChiKey: DAHOOHZYUHETID-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  D,L-2-Methyl-4,5-cis-cyclohexanooxazoline 在 叠氮基三甲基硅烷 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以88%的产率得到N-(trans-2-azidocyclohexyl)acetamide
  参考文献：
  名称：

  A Two-Step Continuous-Flow Synthesis of N-(2-Aminoethyl)acylamides through Ring-Opening/Hydrogenation of Oxazolines

  摘要：

  DOI：

  10.1002/chem.201102772
• 作为产物：
  描述：

  trans-1-(N-acetylamino)-2-bromocyclohexane 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以84%的产率得到D,L-2-Methyl-4,5-cis-cyclohexanooxazoline
  参考文献：
  名称：

  Bromination of alkenes in acetonitrile. A rate and product study

  摘要：

  The reaction of simple alkenes and aryl alkenes with molecular bromine in damp MeCN occurred with solvent incorporation to give 2-bromo-1-(N-acetylamino)alkanes, 2-methyloxazolines, 2-acetoxyalkylamine hydrobromides, and 2-(N-acetylamino) alcohols. These products arose by the transformation of initially formed 2-bromo-1-(N-acetylamino)alkanes obtained by MeCN attack on bromonium or bromocarbonium ions to give nitrilium tribromide salts. These reacted with water to give 2-bromo-1-(N-acetylamino)alkanes. The kinetic profile of the reaction showed a very fast initial reaction of the alkene and Br2 to yield the nitrilium tribromide, followed by a much slower reaction of Br3- with the alkene. The incorporation of MeCN was Markovnikov and stereospecifically anti. The degree to which incorporation of solvent occurred depended upon the alkene structure and the initial reagent concentrations. A rationalization for the observed chemoselectivity and its dependence on the reaction conditions is offered.

  DOI：

  10.1021/jo00009a027

文献信息

• Asymmetric Amidoselenenylation of Alkenes Promoted by Camphorselenenyl Sulfate: A Useful Synthetic Route to Enantiopure Oxazolines
  作者：Marcello Tiecco、Lorenzo Testaferri、Claudio Santi、Cristina Tomassini、Francesca Marini、Luana Bagnoli、Andrea Temperini

  DOI：10.1002/1099-0690(200010)2000:20<3451::aid-ejoc3451>3.0.co;2-q

  日期：2000.10

  Camphorselenenyl sulfate is an efficient chiral, nonracemic electrophilic reagent which can be produced from the easily available camphor diselenide by treatment with ammonium persulfate. This electrophilic selenium reagent reacts with alkenes, at room temperature in acetonitrile, in the presence of water and trifluoromethanesulfonic acid to afford the amidoselenenylation products with moderate facial

  樟脑二硒基硫酸盐是一种有效的手性、非外消旋亲电试剂，可通过过硫酸铵处理从容易获得的樟脑二硒化物制备。这种亲电子硒试剂在室温下在乙腈中，在水和三氟甲磺酸存在下与烯烃反应，以提供具有中等表面选择性的酰胺硒烯基化产物。然而，两种非对映加成产物很容易分离。在用苯基硒基三氟甲磺酸酯或 SO2Cl2 活化硒部分后，这些产物通过分子内取代立体特异性地脱硒并提供对映体纯的恶唑啉。
• Intramolecular Nucleophilic Deselenenylation Reactions Promoted by Benzeneselenenyl Triflate. Stereospecific Synthesis of Vicinal Amino Alcohol Precursors
  作者：Marco Tingoli、Lorenzo Testaferri、Andrea Temperini、Marcello Tiecco

  DOI：10.1021/jo960866g

  日期：1996.1.1

  nitrogen nucleophilic substituents, readily undergoes intramolecular nucleophilic displacement to afford azido-substituted heterocyclic compounds. This intramolecular substitution occurs with inversion of configuration at the carbon atom bearing the selenium atom. Starting from acetamido selenides and carbamato selenides, a stereocontrolled synthesis of the vicinal amino alcohol precursor oxazolines and

  用亲电子亚硒化剂活化后，邻位叠氮基硒化物的苯基硒基含有内部的氧或氮亲核取代基，容易发生分子内亲核取代，得到叠氮基取代的杂环化合物。这种分子内取代发生在带有硒原子的碳原子上的构型反转的情况下。从乙酰氨基硒化物和氨基甲酸酯硒化物开始，已经开发了邻位氨基醇前体恶唑啉和恶唑烷-2-酮的立体控制合成。
• 2-TRIFLUOROMETHYLNICOTINAMIDE DERIVATIVES AS HDL-CHOLESTEROL RAISING AGENTS
  申请人：Hebeisen Paul

  公开号：US20090247588A1

  公开（公告）日：2009-10-01

  The present invention relates to compounds formula I: and pharmaceutically acceptable salts thereof, wherein R 1 to R 8 are as defined in the description and claims for use as HDL-cholesterol raising agents in the treatment and/or prophylaxis of diseases or disorders that can be treated with such agents such as dyslipidemia.

  本发明涉及化合物公式I及其药学上可接受的盐，其中R1至R8在说明书和权利要求书中定义，用作高密度脂蛋白胆固醇升高剂，用于治疗和/或预防可用此类剂治疗的疾病或紊乱，例如脂质代谢异常。
• Nucleophilic attack on olefins initiated by dimethyl(methylthio)sulfonium fluoroborate (DMTSF). Azasulfenylation
  作者：Barry M. Trost、Tohru Shibata

  DOI：10.1021/ja00375a054

  日期：1982.6
• One-Pot Conversion of Alkenes into Oxazolines and Oxazolidin-2-Ones Promoted by Diphenyl Diselenide
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Andrea Temperini、Luana Bagnoli、Claudio Santi

  DOI：10.1080/00397919708005461

  日期：1997.12

  Oxazolines or oxazolidin-2-ones are produced from the reaction of diphenyl diselenide, ammonium persulfate and trifluoromethanesulfonic acid with alkenes in the presence of MeCN/H2O, NH2CN/H2O or NH2CO2Et.