(4S,5S)-4-methyl-2,5-diphenyl-4,5-dihydro-1,3-oxazole | 257952-52-6

• 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,5S)-4-methyl-2,5-diphenyl-4,5-dihydro-1,3-oxazole
• 英文别名: (4S,5S)-4-methyl-2,5-diphenyl-2-oxazoline；4-methyl-2,5-diphenyl-4,5-dihydro-oxazole；2,5-Diphenyl-4-methyloxazolin
• CAS: 257952-52-6
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: FBQLSYLRJWTPGK-SWLSCSKDSA-N

物化性质

• 沸点：
  377.6±31.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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,5S)-4-methyl-2,5-diphenyl-4,5-dihydro-1,3-oxazole 在 盐酸 作用下， 反应 30.0h， 以90%的产率得到盐酸去甲伪麻黄碱
  参考文献：
  名称：

  Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases

  摘要：

  Using a chiral base from a norephedrine-derived diamine, the enantioselective rearrangement of a mesocyclohexene oxide can be performed in 94% yield and with 94% enantioselectivity. The enantioselectivity is lower (86% ee) with the diastereoisomeric chiral base. In order to prepare the diastereoisomeric chiral base, a potentially useful way of converting norephedrine into norpseudophedrine was developed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00432-2
• 作为产物：
  描述：

  去甲麻黄碱 在 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (4S,5S)-4-methyl-2,5-diphenyl-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases

  摘要：

  Using a chiral base from a norephedrine-derived diamine, the enantioselective rearrangement of a mesocyclohexene oxide can be performed in 94% yield and with 94% enantioselectivity. The enantioselectivity is lower (86% ee) with the diastereoisomeric chiral base. In order to prepare the diastereoisomeric chiral base, a potentially useful way of converting norephedrine into norpseudophedrine was developed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00432-2

文献信息

• Direct asymmetric synthesis of oxazolines from olefins using a chiral nitridomanganese complex: a novel three-component coupling leading to chiral oxazolines
  作者：Satoshi Minakata、Masaaki Nishimura、Toru Takahashi、Yoji Oderaotoshi、Mitsuo Komatsu

  DOI：10.1016/s0040-4039(01)01963-3

  日期：2001.12

  A new synthetic method for chiral oxazolines has been developed by N1 unit transfer to olefins using a chiral nitridomanganese complex. When trans-disubstituted styrenes were treated with chiral complex 1 in the presence of an acid chloride, oxazolines were obtained with high enantioselectivities (up to 92% ee). Furthermore, the produced oxazolines could be easily converted into β-amino alcohols, which

  通过使用手性硝基锰锰络合物将N1单元转移到烯烃中，已经开发了一种新的手性恶唑啉合成方法。当在酰氯存在下用手性配合物1处理反式-二取代的苯乙烯时，以高对映选择性（至多92％ee）获得恶唑啉。此外，所产生的恶唑啉可以容易地转化为作为麻黄碱衍生物的β-氨基醇。
• Asymmetric N1 Unit Transfer to Olefins with a Chiral Nitridomanganese Complex:  Novel Stereoselective Pathways to Aziridines or Oxazolines
  作者：Masaaki Nishimura、Satoshi Minakata、Toru Takahashi、Yoji Oderaotoshi、Mitsuo Komatsu

  DOI：10.1021/jo016146d

  日期：2002.4.1

  chiral N-unsubstituted aziridines. It was found that the reaction was applicable to the asymmetric synthesis of 2-oxazolines from olefins when acyl chlorides were employed as activators. Complex 1 provided an effective asymmetric environment for trans-disubstituted styrenes in the reaction (up to 92% ee). This is the first example of a direct asymmetric synthesis of 2-oxazolines from olefins. Additional

  已发现手性硝基锰锰配合物1是从烯烃（例如苯乙烯及其衍生物）不对称合成氮丙啶和2-恶唑啉的高度潜在的N1单元来源。当在吡啶，吡啶N-氧化物和银盐存在下使用磺酰氯作为配合物的活化剂时，烯烃与配合物1的反应顺利进行，得到N-磺酰化氮丙啶。使用2-三甲基甲硅烷基乙烷磺酰氯（SESC1）将苯乙烯衍生物与配合物1进行叠氮化，得到N-SES-氮丙啶，其易于转化为手性N-未取代的氮丙啶。已经发现，当使用酰氯作为活化剂时，该反应适用于由烯烃的不对称合成2-恶唑啉。配合物1为反应中的反式二取代苯乙烯提供了有效的不对称环境（ee高达92％）。这是从烯烃直接不对称合成2-恶唑啉的第一个例子。在该研究过程中进行的另外的实验表明，该反应涉及N-酰基氮丙啶中间体的异构化。
• A Biocatalytic Henry Reaction—The Hydroxynitrile Lyase fromHevea brasiliensis Also Catalyzes Nitroaldol Reactions
  作者：Thomas Purkarthofer、Karl Gruber、Mandana Gruber-Khadjawi、Kerstin Waich、Wolfgang Skranc、Daniel Mink、Herfried Griengl

  DOI：10.1002/anie.200504230

  日期：2006.5.19
• Synthesis of 2-oxazolines mediated by N,N′-diisopropylcarbodiimide
  作者：Stefano Crosignani、Abigail C. Young、Bruno Linclau

  DOI：10.1016/j.tetlet.2004.10.143

  日期：2004.12

  N-(beta-Hydroxy)amides can be cyclised by reaction with diisopropy1carbodiimide (DIC) to give the corresponding 2-oxazolines in high yields. The reaction requires only very mild Lewis-acid catalysis (5mol% Cu(OTf)(2)) and can be accomplished with simple heating, or in very short reaction times under microwave irradiation. (C) 2004 Elsevier Ltd. All rights reserved.
• Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases
  作者：Bob Colman、Simon E de Sousa、Peter O'Brien、Timothy D Towers、Will Watson

  DOI：10.1016/s0957-4166(99)00432-2

  日期：1999.10

  Using a chiral base from a norephedrine-derived diamine, the enantioselective rearrangement of a mesocyclohexene oxide can be performed in 94% yield and with 94% enantioselectivity. The enantioselectivity is lower (86% ee) with the diastereoisomeric chiral base. In order to prepare the diastereoisomeric chiral base, a potentially useful way of converting norephedrine into norpseudophedrine was developed. (C) 1999 Elsevier Science Ltd. All rights reserved.