(4S)-甲基-5,5-二苯基-2-噁唑酮 | 191090-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4S)-甲基-5,5-二苯基-2-噁唑酮
• 中文别名: S-5,5-二苯基-4-甲基-2-恶唑烷酮；S-5,5-二苯基-4-甲基-2-噁唑烷酮；(S)-(?)-5,5-二苯基-4-甲基-2-噁唑烷酮
• 英文名称: (S)-4-Methyl-5,5-diphenyl-oxazolidin-2-one
• 英文别名: (S)-4-Methyl-5,5-diphenyloxazolidin-2-one；(4S)-4-methyl-5,5-diphenyl-1,3-oxazolidin-2-one
• CAS: 191090-29-6
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: URUDVMKJOXKZHR-LBPRGKRZSA-N

物化性质

• 熔点：
  263-267 °C(lit.)
• 沸点：
  465.0±45.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  常温常压下稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S)-甲基-5,5-二苯基-2-噁唑酮 在 吡啶 、 氢氟酸 作用下， 反应 31.0h， 以77%的产率得到(S)-1,1-二苯基-1-氟-2-氨基丙烷
  参考文献：
  名称：

  A synthesis of (S)-α-(fluorodiphenylmethyl)alkylamines by HF–pyridine treatment of 4-alkyl-5,5-diphenyl-oxazolidinones

  摘要：

  Treatment of enantiomerically pure (S)-4-alkyl-5,5-diphenyl-oxazolidinones, themselves derived from appropriate amino acids, with HF-pyridine (Olah's reagent) generated a range of (S)-alpha-(fluoro-diphenylmerhyl)alkylamines. These compounds represent a novel range of fluorinated chiral amines. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00142-7
• 作为产物：
  描述：

  (S)-2-氨基-1,1-二苯基-1-丙醇 、 氯甲酸三氯甲酯 在 三乙胺 作用下， 生成 (4S)-甲基-5,5-二苯基-2-噁唑酮
  参考文献：
  名称：

  A short synthesis of (S)-α-(diphenylmethyl)alkyl amines from amino acids

  摘要：

  A range of (S)-alpha-(diphenylmethyl)alkyl amines were prepared from the corresponding (S)-alpha-amino acid ester hydrochlorides. These amines were derived by direct hydrogenation of their precursor oxazolidinones. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00095-6

文献信息

• Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations
  作者：Jeongjae Yu、Daniel W. Armstrong、Jae Jeong Ryoo

  DOI：10.1002/chir.22766

  日期：2018.1

  We recently reported a new C3‐symmetric (R)‐phenylglycinol N‐1,3,5‐benzenetricarboxylic acid‐derived chiral high‐performance liquid chromatography (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N‐3,5‐dintrobenzoyl (DNB) (R)‐phenylglycinol‐derived CSP. Over a decade ago, (S)‐leucinol, (R)‐phenylglycine, and (S)‐leucine derivatives were used as

  我们最近报道了一种新的C3对称（R）-苯基甘氨醇N -1,3,5-苯三甲酸衍生的手性高效液相色谱（HPLC）固定相（CSP 1），与先前描述的结果相比具有更好的结果N -3,5-二硝基苯甲酰（DNB）（R）-苯基甘氨醇衍生的CSP。十多年前，（S）-亮氨酸，（R）-苯甘氨酸和（S）-亮氨酸衍生物被用作基于3,5-DNB的Pirkle型CSP的手性分离原料。在这项研究中，通过结合上述想法和结果，准备了三个新的C3对称CSP（CSP 2、3和4）。在这里，我们描述了新的C3对称CSP（CSP 2–CSP 4）的合成程序和应用。
• Synthesis and application of <i>N</i> ‐3,5‐dinitrobenzoyl and C ₃ symmetric diastereomeric chiral stationary phases
  作者：Jeong Jae Yu、Jae Jeong Ryoo

  DOI：10.1002/chir.23415

  日期：2022.4

  Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative chiral stationary phases (CSPs) (CSP 1, 2, and 3) and three C3 symmetric CSPs (CSP 4, 5, and 6). The six newly prepared CSPs were applied to the chiral

  三种非对映体手性化合物，即(R,R)-(+)-2-氨基-1,2-二苯乙醇、(1S,2R)-(+)-2-氨基-1,2-二苯乙醇和(1R) ,2R)-(+)-1,2-二苯基乙二胺作为起始原料制备三种N -3,5-二硝基苯甲酰基衍生物手性固定相 (CSPs) (CSP 1, 2, and 3) 和三种 C 3对称 CSPs （CSP 4、5 和 6）。将六种新制备的 CSP 应用于 HPLC 对 44 个手性样品的手性分离。大多数样品在 CSP 6 上分离，在六个新制备的 CSP 中平均分离因子最高。
• Isocyanates, part 5 Synthesis of chiral oxazolidin-2-ones and imidazolidin-2-ones via DMAP-catalyzed isocyanation of amines with di-tert-butyl dicarbonate
  作者：Hans-Joachim Knölker、Tobias Braxmeier

  DOI：10.1016/s0040-4039(98)02194-7

  日期：1998.12

  Oxazolidin-2-ones and imidazolidin-2-ones are prepared under mild reaction conditions by DMAP-catalyzed isocyanation of 1,2-aminoalcohols and 1,2-diamines with di-tert-butyl dicarbonate and subsequent cyclization.

  在温和的反应条件下，通过DMAP催化的1,2-氨基醇和1,2-二胺与二碳酸二叔丁酯的异氰酸酯化反应和随后的环化反应，可制得恶唑烷-2-酮和咪唑烷-2-酮。
• Synthesis of chiral oxazolidin-2-ones by 1,2-amino alcohols, carbon dioxide and electrogenerated acetonitrile anion
  作者：Marta Feroci、Armando Gennaro、Achille Inesi、Monica Orsini、Laura Palombi

  DOI：10.1016/s0040-4039(02)01186-3

  日期：2002.8

  An improved electrochemical synthesis of chiral oxazolidin-2-ones from chiral 1,2-amino alcohols is obtained by direct electrolysis of solutions of MeCN–TEAP containing the amino alcohol, with subsequent CO2 bubbling and addition of TsCl. This synthesis avoids any addition of bases or probases and yields oxazolidinones in high yields.

  通过直接电解含氨基醇的MeCN-TEAP溶液，随后鼓泡CO 2和添加TsCl ，可以从手性1,2-氨基醇中改进手性恶唑烷-2-酮的电化学合成。该合成避免了碱或脯氨酸的任何添加，并以高收率产生了恶唑烷酮。
• Process for preparing chiral compounds
  申请人：The University Court of the University of St. Andrews

  公开号：US07126028B1

  公开（公告）日：2006-10-24

  Process for the preparation of chiral compounds of formula (I) comprising contacting a compound of formula (II) with a source of hydrogen or halide; wherein A is a chiral center; X is selected from oxygen, sulphur and nitrogen; n is selected from 0 and 1 and is equal to the valence of X less 2; B is a fragment CR 3 2; Z is hydrogen or halogen; with the proviso that when X is nitrogen, n is 1, one of R 1 and two of R 2 are hydrogen, BZ is CHPh 2, the other R 1 and R 2 do not form together a five membered heterocyclic (pyrrolidone) ring; novel intermediates, novel compounds, polymers and libraries thereof and the use thereof as fine chemicals, and compositions thereof.

  制备式(I)手性化合物的过程包括将式(II)化合物与氢或卤素源接触；其中A是手性中心；X选择氧、硫或氮；n选择0和1，并等于X的价数减去2；B是片段CR 3 2；Z是氢或卤素；但当X为氮时，n为1，其中一个R 1 和两个R 2 是氢，BZ为CHPh 2，另一个R 1 和R 2 不形成五元杂环（吡咯烷酮）环；新的中间体、新的化合物、聚合物及其库以及作为精细化学品和其组成物的用途。