(S)-3-苯甲酰基-4-苯基甲基-2-恶唑烷酮 | 153729-83-0

• 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: (S)-3-苯甲酰基-4-苯基甲基-2-恶唑烷酮
• 英文名称: (S)-3-benzoyl-4-phenylmethyl-2-oxazolidinone
• 英文别名: 3-benzoyl-4-phenylmethyl-2-oxazolidinone；(4S)-3-benzoyl-4-benzyl-2-oxazolidinone；(S)-3-benzoyl-4-benzyloxazolidin-2-one；N-benzoyl-4-benzyl-2-oxazolidinone；(4S)-3-benzoyl-4-benzyl-1,3-oxazolidin-2-one
• CAS: 153729-83-0
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: VEKBZOWWOPANHP-HNNXBMFYSA-N

物化性质

• 熔点：
  142-145 °C
• 沸点：
  412.0±28.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-苯甲酰基-4-苯基甲基-2-恶唑烷酮 在 ammonium chloride 、 lithium iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以76%的产率得到(4S)-4-benzyl-2-phenyl-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  Decarboxylative Isomerization of N-Acyl-2-oxazolidinones to 2-Oxazolines

  摘要：

  N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25-50 degrees C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.

  DOI：

  10.1021/jo800076f
• 作为产物：
  描述：

  N-甲酰基糖精 在 potassium fluoride 、 palladium diacetate 、 三乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 lithium chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 (S)-3-苯甲酰基-4-苯基甲基-2-恶唑烷酮
  参考文献：
  名称：

  Palladium-Catalyzed Fluorocarbonylation Using N-Formylsaccharin as CO Source: General Access to Carboxylic Acid Derivatives

  摘要：

  N-Formylsaccharin, an easily accessible crystalline compound, has been employed as an efficient CO source in Pd-catalyzed fluorocarbonylation of aryl halides to afford the corresponding acyl fluorides in high yields. The reactions use a near-stoichiometric amount of the CO source (1.2 equiv) and tolerate diverse functional groups. The acyl fluorides obtained could be readily transformed into various carboxylic acid derivatives such as carboxylic acid, esters, thioesters, and amides in a one-pot procedure.

  DOI：

  10.1021/ol4026815

文献信息

• Synthesis of Chiral Selenazolines from <i>N</i>-Acyloxazolidinones via a Selenative Rearrangement of Chiral Cyclic Skeletons
  作者：Fumitoshi Shibahara、Tomoki Fukunaga、Saki Kubota、Akihito Yoshida、Toshiaki Murai

  DOI：10.1021/acs.orglett.8b02520

  日期：2018.9.21

  A synthetic route to chiral selenazolines from readily available N-acyloxazolidinones via a selenative rearrangement of a chiral cyclic skeleton is reported. The reaction proceeds in the presence of elemental selenium, a hydrochlorosilane, and an amine. Although the stability of the obtained selenazoline products is relatively low, a wide range of selenazolines was successfully prepared.

  据报道，通过手性环状骨架的硒化重排，从容易获得的N-酰基恶唑烷二酮合成手性亚硒啉的途径。反应在元素硒，氢氯硅烷和胺的存在下进行。尽管所获得的亚硒唑啉产品的稳定性较低，但是成功制备了多种亚硒唑啉。
• A Convenient Method for the Conversion of <i>N</i>-Acyloxazolidinones to Hydroxamic Acids
  作者：Mukund P. Sibi、Hikaru Hasegawa、Sandeep R. Ghorpade

  DOI：10.1021/ol0263301

  日期：2002.10.1

  Treatment of N-acyloxazolidinones with hydroxylamines using samarium triflate as a Lewis acid provides the corresponding hydroxamic acids in 50-98% yields at room temperature. The conversion proceeds with high degree of chemoselectivity and without racemization of chiral centers alpha- to the acyl group. [reaction: see text]

  使用三氟甲磺酸sa作为路易斯酸，用羟胺处理N-酰基恶唑烷酮，在室温下以50-98％的收率提供相应的异羟肟酸。转化以高度的化学选择性进行，并且手性中心不外消旋地从α到酰基。[反应：看文字]
• Transesterification of N-acyloxazolidinones with alcohol by lanthanum(III) Iodide
  作者：Shin-ichi Fukuzawa、Yuki Hongo

  DOI：10.1016/s0040-4039(98)00521-8

  日期：1998.5

  Transesterification of N-acyloxazolidinones by treatment with an alcohol and lanthanum(III) iodide gives the corresponding esters in good to excellent yields under mild conditions with negligible racemization. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Electrogenerated Base-Induced N-Acylation of Chiral Oxazolidin-2-ones
  作者：Marta Feroci、Achille Inesi、Laura Palombi、Leucio Rossi、Giovanni Sotgiu

  DOI：10.1021/jo010038+

  日期：2001.9.1
• Palladium-Catalyzed Fluorocarbonylation Using <i>N</i>-Formylsaccharin as CO Source: General Access to Carboxylic Acid Derivatives
  作者：Tsuyoshi Ueda、Hideyuki Konishi、Kei Manabe

  DOI：10.1021/ol4026815

  日期：2013.10.18

  N-Formylsaccharin, an easily accessible crystalline compound, has been employed as an efficient CO source in Pd-catalyzed fluorocarbonylation of aryl halides to afford the corresponding acyl fluorides in high yields. The reactions use a near-stoichiometric amount of the CO source (1.2 equiv) and tolerate diverse functional groups. The acyl fluorides obtained could be readily transformed into various carboxylic acid derivatives such as carboxylic acid, esters, thioesters, and amides in a one-pot procedure.