(4S)-3-<(s'S)-2'-(4-isobutylphenyl)propanoyl>-4-(1-methylethyl)-2-oxazolidinone | 136436-80-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4S)-3-<(s'S)-2'-(4-isobutylphenyl)propanoyl>-4-(1-methylethyl)-2-oxazolidinone
• 英文别名: (4S)-3-[(2S)-2-(4-isobutylphenyl)propionyl]-4-isopropyloxazolidin-2-one；(4S,2'S)-4-isopropyl-3-[2'-(4-isobutylphenyl)propanoyl]oxazolidin-2-one；(4S)-3-[(s'S)-2'-(4-isobutylphenyl)propanoyl]-4-(1-methylethyl)-2-oxazolidinone；(4S)-3-[(2S)-2-[4-(2-methylpropyl)phenyl]propanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 136436-80-1
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: VZZGHVTZXROLQE-WMLDXEAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  (4S)-3-<(s'S)-2'-(4-isobutylphenyl)propanoyl>-4-(1-methylethyl)-2-oxazolidinone 在 lithium hydroxide 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到(S)-4-异丙基-2-唑烷酮
  参考文献：
  名称：

  On the structure and chiroptical properties of (S)-4-isopropyl-oxazolidin-2-one

  摘要：

  The specific rotation of (S)-4-isopropyl-oxazolidin-2-one is extremely solvent dependent. In chloroform it is dextrorotatory {[alpha](D)(26) = + 15.5 (c 5.2, CHCl3)}, whereas in ethanol it is levorotatory {[alpha](D)(26) = -16.1 (c 5.2; EtOH)}. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.032
• 作为产物：
  描述：

  异丁芬酸 在 正丁基锂 、 氯化亚砜 、 lithium diisopropyl amide 作用下， 反应 3.5h， 生成 (4S)-3-<(s'S)-2'-(4-isobutylphenyl)propanoyl>-4-(1-methylethyl)-2-oxazolidinone
  参考文献：
  名称：

  2-芳基丙酸的不对称合成

  摘要：

  摘要 (S)-2-(6-甲氧基-2-萘基)丙酸(S-Naproxen) 1 和(S)-2-(4-异丁基苯基)丙酸(S-Ibuprofen) 2 的制备，基于报道了恶唑烷酮 9 和 14 的不对称烷基化。

  DOI：

  10.1080/00397919108021282

文献信息

• Efficient parallel resolution of pentafluorophenyl active esters using quasi-enantiomeric combinations of oxazolidin-2-ones
  作者：Najla Al Shaye、Sameer Chavda、Elliot Coulbeck、Jason Eames、Yonas Yohannes

  DOI：10.1016/j.tetasy.2011.02.021

  日期：2011.2

  The parallel resolution of racemic pentafluorophenyl 2-aryl/phenylpropanoates and butanoates using an equimolar combination of quasi-enantiomeric Evans oxazolidin-2-ones is discussed. The levels of diastereoselectivity were excellent (>90% de) leading to separable quasi-enantiomeric oxazolidin-2-ones in good yield. This methodology was used to resolve a series of structurally related 2-aryl/phenylpropanoic and butanoic acids. (C) 2011 Elsevier Ltd. All rights reserved.
• Copper(II)-catalyzed kinetic resolution of (±)-2-arylpropionic acids with chiral N-trimethylsilyloxazolidin-2-one
  作者：Shin-ichi Fukuzawa、Yoshiaki Chino、Tetsuhiro Yokoyama

  DOI：10.1016/s0957-4166(02)00409-3

  日期：2002.8

  The reaction between (+/-)-2-arylpropanoyl chlorides 1 (2 equiv.) and enantiopure N-trimethylsilyoxazolidin-2-one 2 in the presence of a catalytic amount of CuCl2 in hexane affords the corresponding N-acyloxazolidin-2-one in good chemical yields (97%) with up to 50% de. (C) 2002 Elsevier Science Ltd. All rights reserved.
• On the structure and chiroptical properties of (S)-4-isopropyl-oxazolidin-2-one
  作者：David Benoit、Elliot Coulbeck、Jason Eames、Majid Motevalli

  DOI：10.1016/j.tetasy.2008.03.032

  日期：2008.5

  The specific rotation of (S)-4-isopropyl-oxazolidin-2-one is extremely solvent dependent. In chloroform it is dextrorotatory [alpha](D)(26) = + 15.5 (c 5.2, CHCl3)}, whereas in ethanol it is levorotatory [alpha](D)(26) = -16.1 (c 5.2; EtOH)}. (C) 2008 Elsevier Ltd. All rights reserved.
• Asymmetric Synthesis of 2-Arylpropionic Acids
  作者：Asensio González

  DOI：10.1080/00397919108021282

  日期：1991.6

  Abstract The preparation of (S)-2-(6-methoxy-2-naphtyl)propionic acid (S-Naproxen) 1 and (S)-2-(4-isobutylphenyl)propionic acid (S-Ibuprofen) 2, based on asymmetric alkylation of oxazolidiones 9 and 14, is reported.

  摘要 (S)-2-(6-甲氧基-2-萘基)丙酸(S-Naproxen) 1 和(S)-2-(4-异丁基苯基)丙酸(S-Ibuprofen) 2 的制备，基于报道了恶唑烷酮 9 和 14 的不对称烷基化。