(4S-trans)-4,5-dihydro-4-isobutyl-2-phenyl-5-vinyl-oxazoline | 257296-66-5

• 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: (4S-trans)-4,5-dihydro-4-isobutyl-2-phenyl-5-vinyl-oxazoline
• 英文别名: (4S,5S)-5-ethenyl-4-(2-methylpropyl)-2-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 257296-66-5
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: IQDTUYRBRWAFKB-KBPBESRZSA-N

物化性质

• 沸点：
  323.7±31.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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-4-isobutyl-2-phenyl-5-vinyl-oxazoline 在 盐酸 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 N-((3S,4S)-O-MTPA-3-hydroxy-6-methyl-1-heptenyl)benzamide
  参考文献：
  名称：

  Stereoselective Intramolecular Cyclization of Allyl and Homoallyl Benzamide via π-Allylpalladium Complex Catalyzed by Pd(0)

  摘要：

  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.

  DOI：

  10.1021/jo991065r
• 作为产物：
  描述：

  N-叔丁氧羰基-L-亮氨醇 在 吡啶 、 盐酸 、 四(三苯基膦)钯 、 三氟化硼乙醚 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 、 苯 为溶剂， 反应 43.25h， 生成 (4S-trans)-4,5-dihydro-4-isobutyl-2-phenyl-5-vinyl-oxazoline
  参考文献：
  名称：

  Stereoselective Intramolecular Cyclization of Allyl and Homoallyl Benzamide via π-Allylpalladium Complex Catalyzed by Pd(0)

  摘要：

  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.

  DOI：

  10.1021/jo991065r

文献信息

• 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 Intramolecular Oxazine Formation by a π-Allylpalladium Complex Catalyzed by Pd0
  作者：Jae-Eun Joo、Kee-Young Lee、Van-Thoai Pham、Won-Hun Ham

  DOI：10.1002/ejoc.200600927

  日期：2007.4

  An efficient procedure for synthesizing oxazines was developed by the palladium(0)-catalyzed intramolecular cyclization of a benzamide through a π-allylpalladium(II) complex. Unlike other palladium-catalyzed reactions, the temperature was found to be a key factor in determining the stereochemistry of the oxazine. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  通过钯（0）催化的苯甲酰胺通过π-烯丙基钯（II）络合物进行分子内环化，开发了合成恶嗪的有效方法。与其他钯催化反应不同，发现温度是决定恶嗪立体化学的关键因素。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• US6127546A
  申请人：——

  公开号：US6127546A

  公开（公告）日：2000-10-03