(2R,4S,5R)-3,4-dimethyl-2,5-diphenyloxazolidine | 29843-09-2

• 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: (2R,4S,5R)-3,4-dimethyl-2,5-diphenyloxazolidine
• 英文别名: (2R)-3,4t-dimethyl-2r,5t-diphenyl-oxazolidine；(2R)-3,4t-Dimethyl-2r,5t-diphenyl-oxazolidin；(2R,4S,5R)-3,4-dimethyl-2,5-diphenyl-1,3-oxazolidine
• CAS: 29843-09-2
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: UYHFNMAZLZQLFT-RRQGHBQHSA-N

物化性质

• 沸点：
  366.9±30.0 °C(Predicted)
• 密度：
  1.059±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苄基碘 、 (2R,4S,5R)-3,4-dimethyl-2,5-diphenyloxazolidine 生成 (1R)-N-methyl-1,2-diphenylethanamine
  参考文献：
  名称：

  Asymmetric synthesis. II. Synthesis and absolute configuration of oxazolidines derived from (-)-ephedrine and aromatic aldehydes

  摘要：

  DOI：

  10.1021/jo00815a012
• 作为产物：
  描述：

  麻黄碱 、 苯甲醛 生成 (2R,4S,5R)-3,4-dimethyl-2,5-diphenyloxazolidine
  参考文献：
  名称：

  213.麻黄碱对苯甲醛的作用

  摘要：

  DOI：

  10.1039/jr9320001580

文献信息

• Heterogeneous rhodium-catalyzed hydrogenation conditions for the highly effective synthesis of 1,3-oxazolidines from 1,2-amino alcohols and nitriles
  作者：Stéphane Létinois、Jean-Christophe Dumur、Françoise Hénin、Jacques Muzart

  DOI：10.1016/s0040-4039(98)00192-0

  日期：1998.4

  for the synthesis of 1,3-oxazolidines in high yields using 1,2-amino alcohols, nitriles, an atmospheric pressure of hydrogen and catalytic quantites of rhodium on carbon powder is presented. This reaction probably involves the semi-hydrogenation of the nitrile followed by condensation with the amino alcohol. The process may constitute the key step in a two-step sequence for reducing a nitrile into the

  提出了使用1，2-氨基醇，腈，氢气的大气压和铑在碳粉上的催化量来容易地以高产率合成1，3-恶唑烷的方法。该反应可能涉及腈的半氢化，然后与氨基醇缩合。该方法可以按两步顺序构成关键步骤，以将腈还原为相应的醛。
• Stereochemistry-60
  作者：Claude Agami、Toufic Rizk

  DOI：10.1016/s0040-4020(01)96496-8

  日期：1985.1

  controlled oxazolidine formation was observed with aromatic aldehydes substituted by electron-withdrawing groups. The stereoselectivity is solvent dependent: non-stereoselective ring closure occurred in chloroform while a high diastereodifferentiation was observed in methanol. The first oxazolidine showing an unambiguous 2R configuration was synthesized from p-bromobenzaldehyde and (-)-ephedrine in alcohol

  用吸电子基团取代的芳族醛观察到动力学控制的恶唑烷的形成。立体选择性取决于溶剂：在氯仿中发生非立体选择性闭环，而在甲醇中观察到高非对映异构性。由对-溴苯甲醛和（-）-麻黄碱在酒精介质中合成了第一个具有清晰2R构型的恶唑烷。为了阐明立体选择性的差异，提出了一种涉及由醇类溶剂进行亲核辅助的机理。
• Role of solvent on the diastereoselectivity of oxazolidine formation from (–)-ephedrine
  作者：Claude Agami、Toufic Rizk

  DOI：10.1039/c39830001485

  日期：——

  Under kinetic control, the stereochemical course of the condensation between (–)-ephedrine and p-cyano-or p-nitro-benzaldehyde is solvent dependent; no noticeable stereoselectivity was observed in chloroform whereas diastereo-differentiation occurred in methanol.

  在动力学控制下，（-）-麻黄碱与对-氰基-或对-硝基-苯甲醛之间缩合的立体化学过程取决于溶剂。在氯仿中没有观察到明显的立体选择性，而在甲醇中发生了非对映异构。
• Comparison of Conventional and Microwave Assisted Reactions Giving Aromatic Oxazolidines
  作者：Florian Diwischek、Eberhard Heller、Ulrike Holzgrabe

  DOI：10.1007/s00706-003-0020-6

  日期：2003.8.1

  By reaction of aromatic aldehydes with (-)-ephedrine aromatic 1,3-oxazolidines can be obtained. The reaction was carried out either at conventional conditions or by microwave heating. The different diastereomeric ratios were determined by Means of H-1 NMR spectroscopy.