2-phenyl-3a,4,5,6,7,7a-hexahydro-benzooxazole | 57437-13-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenyl-3a,4,5,6,7,7a-hexahydro-benzooxazole
• 英文别名: 2-Phenyl-3a,4,5,6,7,7a-hexahydro-1,3-benzoxazole
• CAS: 57437-13-5
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: IIERPKDURDRYMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  2-phenyl-3a,4,5,6,7,7a-hexahydro-benzooxazole 在 乙醛 、 间氯过氧苯甲酸 作用下， 反应 25.5h， 生成 (2-氧代环己基)苯甲酸酯
  参考文献：
  名称：

  Oxidation of bicyclic oxazolines: applications to glycomimetics and novel saccharide derivatives

  摘要：

  A general procedure is reported for the oxidation Of Substituted oxazolines to alpha-acyloxyketoximes and the derived alpha-acyloxyketones. In the case of oxazolines derived from 2-acetamido-2-deoxyhexoses, the resulting 2-oximinoesters can be converted to 2-nitroglycals. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02161-x
• 作为产物：
  描述：

  N-(2-fluorocyclohexyl)benzamide 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 47.0h， 以47%的产率得到2-phenyl-3a,4,5,6,7,7a-hexahydro-benzooxazole
  参考文献：
  名称：

  Ring opening of aziridines by different fluorinating reagents: three synthetic routes to .alpha.,.beta.-fluoro amines with different stereochemical pathways

  摘要：

  DOI：

  10.1021/jo00337a024

文献信息

• Tellurium-based organic synthesis: A novel one-pot formation of 2-oxazolines from alkenes induced by amidotellurinylation
  作者：Nan X. Hu、Yoshio Aso、Tetsuo Otsubo、Fumio Ogura

  DOI：10.1016/0040-4039(88)85332-2

  日期：1988.1

  Benzenetellurinyl trifluoroacetate readily reacts with alkenes in acetonitrile in the presence of boron trifluoride etherate at 75 °C to give 2-oxazolines via amidotellurinylation.

  在三氟化硼醚化物的存在下，在75°C的条件下，三氟乙酸苄基鸟嘌呤酯容易与乙腈中的烯烃反应，通过酰胺基碲酰化反应生成2-恶唑啉。
• [EN] SYNTHESIS OF OXAZOLINE COMPOUNDS<br/>[FR] SYNTHÈSE DE COMPOSÉS D'OXAZOLINE
  申请人：UNIV HONG KONG POLYTECHNIC

  公开号：WO2010015211A1

  公开（公告）日：2010-02-11

  The present invention provides an improved process for preparing an oxazoline compound of the formula: (I) wherein R1 and R2 are independently hydrogen, sulfide, sulfoxide, sulfonyl, optionally substituted lower alkyl, optionally substituted aralkyl, optionally substituted aryl or optionally substituted polycyclic arylyl; or R1 and R2 combined together with the carbon atoms to which they are attached form an optionally substituted fused 6-member aromatic ring provided that R1 and R2 are attached to carbon atoms adjacent to each other; and R3 is hydrogen, sulfide, sulfoxide, sulfonyl, optionally substituted lower alkyl, optionally substituted aralkyl, optionally substituted aryl or optionally substituted polycyclic arylyl; or an enantiomer therof; or an enantiomeric mixture therof; comprising the step of contacting an acylamino alcohol compound to a suitable amount of fluoroalkanesulfonyl fluoride compound and organic basic reagent. By using a fluoroalkanesulfonyl fluoride compound with an organic basic reagent, the present invention efficiently converts acylamino alcohol compounds into highly chemoselective oxazoline compounds with a remarkable variety of substrates, mild conditions and relatively short reaction time.

  本发明提供了一种改进的制备氧杂环丙烯酮化合物的方法，其化学式为：(I)，其中R1和R2分别为氢、硫化物、亚氧化物、磺酰基、可选择取代的较低烷基、可选择取代的芳基烷基、可选择取代的芳基或可选择取代的多环芳基；或者R1和R2与它们附着的碳原子结合在一起形成可选择取代的融合6-环芳香环，前提是R1和R2附着在彼此相邻的碳原子上；而R3为氢、硫化物、亚氧化物、磺酰基、可选择取代的较低烷基、可选择取代的芳基烷基、可选择取代的芳基或可选择取代的多环芳基；或其对映体；或其对映体混合物；包括将酰胺醇化合物与适量的氟代烷磺酰氟化合物和有机碱性试剂接触的步骤。通过使用氟代烷磺酰氟化合物和有机碱性试剂，本发明能够高效地将酰胺醇化合物转化为高度化学选择性的氧杂环丙烯酮化合物，适用于多种底物，反应条件温和，反应时间相对较短。
• Scandium Triflate Catalyzed Aminolysis of <i>meso</i>-Aziridines
  作者：Christoph Schneider、Saravanan Peruncheralathan、Michael Henze

  DOI：10.1055/s-2007-984920

  日期：——

  The aminolysis of meso-N-phenyl aziridines is efficiently catalyzed with just 1 mol% of Sc(OTf)3 and furnishes valuable 1,2-diamines in good to excellent yields.

  仅用 1 mol% 的 Sc(OTf)3 就能高效催化中-N-苯基氮丙啶的氨解反应，并以良好到极佳的产率获得有价值的 1,2-二胺。
• Synthesis of β-Fluoroamines by Lewis Base Catalyzed Hydrofluorination of Aziridines
  作者：Julia A. Kalow、Dana E. Schmitt、Abigail G. Doyle

  DOI：10.1021/jo300433a

  日期：2012.4.20

  Lewis base catalysis promotes the in situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol. The hydrofluorination of aziridines to provide beta-fluoroamines using this latent HF source is described. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Examples of regio- and diastereoselective ring opening to access medicinally relevant beta-fluoroamine building blocks are presented.
• OGURA, FUMIO;OTSUBO, TEHTSUO;ASO, JOSIO;KO, MINABOSI
  作者：OGURA, FUMIO、OTSUBO, TEHTSUO、ASO, JOSIO、KO, MINABOSI

  DOI：——

  日期：——