(4S-trans)-4,5-dihydro-2,4-diphenyl-5-vinyloxazoline | 216769-41-4

• 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: (4S-trans)-4,5-dihydro-2,4-diphenyl-5-vinyloxazoline
• 英文别名: 2,4-diphenyl-5-vinyl-4,5-dihydrooxazole；(4S-trans)4,5-dihydro-2,4-diphenyl-5-vinyl-oxazoline；(4S,5S)-5-ethenyl-2,4-diphenyl-4,5-dihydro-1,3-oxazole
• CAS: 216769-41-4
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: FORBROKGYUBRID-HOTGVXAUSA-N

物化性质

• 沸点：
  387.5±42.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (4S-trans)-4,5-dihydro-2,4-diphenyl-5-vinyloxazoline 在 palladium dihydroxide 氢气 、 臭氧 、 N,N-二异丙基乙胺 、 红铝 、 仲丁醇 、 lithium chloride 、 copper(I) bromide 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 、 乙腈 为溶剂， -78.0~20.0 ℃ 、482.63 kPa 条件下， 反应 72.0h， 生成 (5S,6S)-5-hydroxy-6-phenylpiperidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of (+)-L-733,060

  摘要：

  A concise, stereocontrolled synthesis of (+)-L-733,060 was achieved. Key features involve diastereoselective oxazoline formation catalyzed by palladium(0) and intramolecular cyclization by catalytic hydrogenation of an oxazoline. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.025
• 作为产物：
  描述：

  L-苯甘氨酸 在 吡啶 、 盐酸 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 三氟化硼乙醚 、 二异丁基氢化铝 、 potassium carbonate 、 1-羟基苯并三唑 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 乙腈 、 叔丁醇 为溶剂， 反应 24.0h， 生成 (4S-trans)-4,5-dihydro-2,4-diphenyl-5-vinyloxazoline
  参考文献：
  名称：

  紫杉醇C-13侧链的高度立体控制的不对称合成；（4S，5R）-2,4-二苯基恶唑啉-5-羧酸

  摘要：

  使用钯催化的恶唑啉形成反应，从市售氨基酸可实现立体选择合成（4S，5R）-2,4-二苯基恶唑啉-5-羧酸（紫杉醇C-13侧链的前体）。

  DOI：

  10.1016/s0040-4039(98)01804-8

文献信息

• Stereospecific Ring Expansion of Chiral Vinyl Aziridines
  作者：Matthew Brichacek、Mauricio Navarro Villalobos、Alexandra Plichta、Jon T. Njardarson

  DOI：10.1021/ol200263g

  日期：2011.3.4

  In this report, it is demonstrated that chiral vinyl aziridines can be stereospecifically ring expanded. This synthetic approach allows controlled access to chiral 2,5-cis- or 2,5-trans-3-pyrroline products from starting materials with the appropriate aziridine geometry. Twenty three ring expansion examples, most of which feature a stereospecific cyclization, are presented.

  在这份报告中，证明了手性乙烯基氮丙啶可以立体有择地扩环。这种合成方法允许从具有适当氮丙啶几何结构的起始材料中受控地获得手性 2,5-顺式- 或 2,5-反式-3- 吡咯啉产物。介绍了二十三个环扩展示例，其中大多数具有立体特异性环化。
• Process for the preparation of oxazoline compound
  申请人：Dong Kook Pharmaceutical Co., Ltd.

  公开号：US06127546A1

  公开（公告）日：2000-10-03

  The present invention relates to a process for the preparation of an oxazoline compound which is easily chemically converted to a beta-amino-alpha-hydroxy acid or a gamma-amino-beta-hydroxy acid. The method comprises producing a compound of the following formula (4) using .alpha.-amino acid. The produced compound (4) is subjected to an intramolecular cyclization to produce an oxazoline compound of the following formula (3). The oxazoline compound (3) is oxidized at a vinyl group with RuCl.sub.3 or NaIO.sub.4 to produce an oxazoline compound of the following formula (1) which is easily chemically converted to a beta-amino-alpha-hydroxy acid. Alternatively, the oxazoline compound (3) may also be treated with 9-borabiclo[3.3.1]nonane such that a hydroxy group is introduced into the end of the vinyl group of the oxazoline compound(3). The introduced end hydroxy group is oxidized with RuCl.sub.3 or NaIO.sub.4 to produce an oxazoline compound of the following formula (2) which is easily chemically converted to a gamma-amino-hydroxy acid.

  本发明涉及一种制备易于化学转化为β-氨基-α-羟基酸或γ-氨基-β-羟基酸的噁唑啉化合物的方法。该方法包括使用α-氨基酸生产以下式(4)的化合物。所生产的化合物(4)经过分子内环化反应，生成以下式(3)的噁唑啉化合物。噁唑啉化合物(3)使用RuCl.sub.3或NaIO.sub.4在乙烯基上进行氧化，生成以下式(1)的噁唑啉化合物，该化合物易于化学转化为β-氨基-α-羟基酸。或者，噁唑啉化合物(3)也可以使用9-硼杂-3.3.1-壬烷进行处理，使得羟基引入到噁唑啉化合物(3)的乙烯基末端。引入的末端羟基使用RuCl.sub.3或NaIO.sub.4进行氧化，生成以下式(2)的噁唑啉化合物，该化合物易于化学转化为γ-氨基-羟基酸。
• Stereoselective synthesis of oxazoline derivative
  申请人：Dong Kook Pharmaceutical Co., Ltd.

  公开号：US06143900A1

  公开（公告）日：2000-11-07

  The present invention relates to stereoselective synthetic method of oxazoline derivative. More particularly, it relates to a synthetic method of oxazoline derivative having the structure of formula I. ##STR1## wherein R represents phenyl, benzyl, methyl, ethyl, isopropyl, isobutyl, cyclohexyl or cyclohexylmethyl.

  本发明涉及一种噁唑啉衍生物的立体选择性合成方法。更具体地，它涉及一种具有式I结构的噁唑啉衍生物的合成方法。其中，R代表苯基、苄基、甲基、乙基、异丙基、异丁基、环己基或环己基甲基。
• Stereoselective Intramolecular Cyclization of Allyl and Homoallyl Benzamide via π-Allylpalladium Complex Catalyzed by Pd(0)
  作者：Kee-Young Lee、Yong-Hyun Kim、Min-Sung Park、Chang-Young Oh、Won-Hun Ham

  DOI：10.1021/jo991065r

  日期：1999.12.1

  The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis of Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same pi-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of beta-amino-alpha-hydroxy acids 1 and gamma-amino-beta-hydroxy acids 2, conveniently protected as oxazoline.
• STEREOSELECTIVE SYNTHESIS OF OXAZOLINE DERIVATIVE
  申请人：DONG KOOK PHARMACEUTICAL CO., LTD.

  公开号：EP1140874A1

  公开（公告）日：2001-10-10