(4S-trans)-4,5-dihydro-4-benzyl-2-phenyl-5-vinyloxazoline | 208935-28-8

• 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-benzyl-2-phenyl-5-vinyloxazoline
• 英文别名: (4S-trans)-4,5-dihydro-2-phenyl-4-benzyl-5-vinyl-oxazoline；(4S-trans)-4,5-dihydro-4-benzyl-2-phenyl-5-vinyl-oxazoline；(4S,5S)-4-benzyl-5-ethenyl-2-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 208935-28-8
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: RJEKQYCGYTZSQZ-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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-benzyl-2-phenyl-5-vinyloxazoline 在 ruthenium trichloride 4-二甲氨基吡啶 、 sodium periodate 、 9-borabicyclo[3.3.1]nonane dimer 、 碳酸氢钠 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 13.0h， 生成 1-((4S,5S)-4-benzyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-undecan-2-one
  参考文献：
  名称：

  Facile and Efficient Total Synthesis of (+)-Preussin

  摘要：

  The enantioselective total synthesis of (+)-preussin, a potent antifungal agent, has been achieved, The key steps are a Pd(0)-catalyzed oxazoline forming reaction from L-phenylalanine, hydrogenolysis, and subsequent diastereoselective reductive cyclization of the intermediate aminoketone to pyrrolidine using Pearlman's catalyst.

  DOI：

  10.1021/ol000289p
• 作为产物：
  描述：

  N-((2S)-3-acetoxy-1-phenyl-4-pentenyl)benzamide 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 乙腈 为溶剂， 以83%的产率得到(4S-trans)-4,5-dihydro-4-benzyl-2-phenyl-5-vinyloxazoline
  参考文献：
  名称：

  Facile and Efficient Total Synthesis of (+)-Preussin

  摘要：

  The enantioselective total synthesis of (+)-preussin, a potent antifungal agent, has been achieved, The key steps are a Pd(0)-catalyzed oxazoline forming reaction from L-phenylalanine, hydrogenolysis, and subsequent diastereoselective reductive cyclization of the intermediate aminoketone to pyrrolidine using Pearlman's catalyst.

  DOI：

  10.1021/ol000289p

文献信息

• Hydrogen Bond Directed Highly Regioselective Palladium-Catalyzed Allylic Substitution
  作者：Gregory R. Cook、Hui Yu、S. Sankaranarayanan、P. Sathya Shanker

  DOI：10.1021/ja028426w

  日期：2003.4.1

  The palladium-catalyzed allylic substitution of 5-vinyloxazolidinones and derivatives was investigated. Unusual and high regioselectivity for the branched product was observed. The regioselectivity was influenced by the type of substrate, the solvents, and the nucleophile. Imide-type nucleophiles were found to be directed to the internal carbon (branched:linear, 75:25 to >98:2), whereas sulfonamides

  研究了钯催化的 5-乙烯基恶唑烷酮和衍生物的烯丙基取代。观察到支化产物的异常和高区域选择性。区域选择性受底物类型、溶剂和亲核试剂的影响。发现酰亚胺型亲核试剂指向内部碳（支链：线性，75:25 至 >98:2），而磺酰胺、胺和丙二酸酯仅添加到烯丙基复合物的末端碳。相对非极性的溶剂如甲苯和四氢呋喃有利于支化产物（分别为 97:3 和 95:5）。乙腈和二氯甲烷提供较低的区域选择性（分别为 50:50 和 67:33），而质子溶剂乙醇的使用导致区域选择性的逆转（12:88）。基板上的导向组很重要。酰胺几乎完全形成支化产物，氨基甲酸酯得到区域异构体的 50:50 混合物，邻苯二甲酰亚胺作为亲核试剂。亲核试剂通过氢键定向的证据是通过用甲基取代酰胺的氢获得的，导致仅产生正常的线性产物。
• 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 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)
• Palladium-catalyzed formation and stereoselective isomerization of 5-vinyloxazolines. Application to the formal synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid
  作者：Gregory R. Cook、P. Sathya Shanker

  DOI：10.1016/s0040-4039(98)00534-6

  日期：1998.5

  Vinyloxazolidinones have been found to undergo Pd(0)-catalyzed ionization followed by loss of carbon dioxide and subsequent cyclization to form vinyloxazolines. The reaction occurred under mild conditions, and enhancement of diastereomeric ratios with chiral substrates was obtained. 4-Benzyl-5-vinyloxazoline prepared by this method has been utilized in the stereoselective synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA). (C) 1998 Elsevier Science Ltd. All rights reserved.