trans-5-phenyl-2-oxooxazolidine-4-carboxylic acid | 50706-19-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-5-phenyl-2-oxooxazolidine-4-carboxylic acid
• 英文别名: 2-oxo-5t-phenyl-oxazolidine-4r-carboxylic acid；(+/-)-2-Oxo-5t-phenyl-oxazolidin-4r-carbonsaeure；DL-trans-2-Oxo-5-phenyl-oxazolidin-4-carbonsaeure；DL-trans-5-Phenyl-oxazolid-2-on-4-carbonsaeure；D,L-trans-4-Carboxy-5-phenyloxazolidon；(4S,5R)-2-oxo-5-phenyloxazolidine-4-carboxylic acid；(4S,5R)-2-oxo-5-phenyl-1,3-oxazolidine-4-carboxylic acid
• CAS: 50706-19-9；50706-23-5；90924-74-6；127913-31-9；135027-30-4
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: SYJOFPCRKHOCEG-JGVFFNPUSA-N

物化性质

• 沸点：
  555.8±50.0 °C(Predicted)
• 密度：
  1.393±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-5-phenyl-2-oxooxazolidine-4-carboxylic acid 在 盐酸 作用下， 生成 2-oxo-4-phenyl-oxazolidine-4-carboxylic acid
  参考文献：
  名称：

  The Interaction of Certain a-(4-Morpholinyl)alkyl Aryl Ketones with Potassium Cyanide and Ammonium Carbonate

  摘要：

  DOI：

  10.1021/jo01177a600
• 作为产物：
  描述：

  1-苯基-2-丙烯-1-醇 在 (-)-DMT 咪唑 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 lithium hydroxide 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 生成 trans-5-phenyl-2-oxooxazolidine-4-carboxylic acid
  参考文献：
  名称：

  Rapid synthesis of β-hydroxy-α-amino acids, such as L-threonine, β-hydroxyphenylalanine, and β-hydroxyleucine, via an application of the sharpless asymmetric epoxidation

  摘要：

  DOI：

  10.1016/s0040-4039(00)70638-1

文献信息

• Direct Access to <i>N</i>-H-Aziridines from Asymmetric Catalytic Aziridination with Borate Catalysts Derived from Vaulted Binaphthol and Vaulted Biphenanthrol Ligands
  作者：Zhenjie Lu、Yu Zhang、William D. Wulff

  DOI：10.1021/ja069371r

  日期：2007.6.6

  The asymmetric catalytic aziridination reaction (AZ reaction) of N-dianisylmethylimines (N-DAM-imines) with ethyl diazoacetate is developed with chiral catalysts prepared from triphenylborate and both the vaulted binaphthol (VANOL) and vaulted biphenanthrol (VAPOL) ligands. Catalysts derived from both ligands were equally effective in terms of asymmetric induction, but the VANOL catalyst was slightly

  N-二茴香基甲基亚胺 (N-DAM-亚胺) 与重氮乙酸乙酯的不对称催化氮丙啶化反应 (AZ 反应) 是使用由硼酸三苯酯和拱形联萘 (VANOL) 和拱形联苯蒽 (VAPOL) 配体制备的手性催化剂开发的。衍生自两种配体的催化剂在不对称诱导方面同样有效，但 VANOL 催化剂稍快。使用 VANOL 催化剂可实现高达 400 次转换，同时仍保持氮丙啶产物中 > 或 = 90% ee。配体可以以 95% 的收率回收而不会损失光学纯度。使用芳基亚胺观察到极好的不对称诱导，尽管观察到烷基取代的亚胺的诱导稍低，但来自所有亚胺底物的氮丙啶的光学纯度可以提高到> 或 = 99% ee，单晶。开发了在酸性条件下对 N-DAM-氮丙啶脱保护的方法，而不会引起酸促进的开环。使用烷基取代的氮丙啶和芳基取代的氮丙啶均可获得优异的 NH-氮丙啶收率。最后，用 Boc、甲苯磺酰基和 Fmoc 基团实现了 NH-氮丙啶的
• Thiazolidone compounds and method of using the same as a vasodilator
  申请人：Sankyo Company, Limited

  公开号：US05298516A1

  公开（公告）日：1994-03-29

  Compounds of formula (I): ##STR1## wherein W represents a sulfur atom and X represents a group of formula --N(R.sup.1)--, or W represents a group of formula --N(R.sup.1)-- and X represents a sulfur atom; R.sup.1 is hydrogen, alkyl or aralkyl; R.sup.2 and R.sup.3 are each hydrogen, alkyl, aralkyl, aryl or aromatic heterocyclic; R.sup.4 is hydrogen, alkyl or aralkyl; and A is alkylene which is optionally substituted by carboxy; and pharmaceutically acceptable salts and esters thereof, have a valuable vasodilatory activity.

  式(I)的化合物：##STR1##其中W代表硫原子，X代表式--N(R.sup.1)--的基团，或者W代表式--N(R.sup.1)--的基团，X代表硫原子；R.sup.1是氢、烷基或芳基烷基；R.sup.2和R.sup.3分别是氢、烷基、芳基烷基、芳基或芳香杂环；R.sup.4是氢、烷基或芳基烷基；A是烷基，可以选择性地被羧基取代；以及其药学上可接受的盐和酯，具有有价值的血管扩张活性。
• Short Synthesis of (+)‐Actinobolin: Simple Entry to Complex Small‐Molecule Inhibitors of Protein Synthesis
  作者：Prabhakara R. Tharra、Andrey A. Mikhaylov、Jiří Švejkar、Marina Gysin、Sven N. Hobbie、Jakub Švenda

  DOI：10.1002/anie.202116520

  日期：2022.4.19

  Bactobolins are complex inhibitors of protein synthesis that target a novel site of the bacterial ribosome. A simple synthetic process by which (−)-quinic acid, L-threonine and L-alanine are combined to yield (+)-actinobolin is reported. The modularity of the approach unlocks new possibilities in analog synthesis.

  Bactobolins 是针对细菌核糖体新位点的蛋白质合成的复杂抑制剂。报道了一种简单的合成方法，通过该方法将 (-)-奎尼酸、L-苏氨酸和 L-丙氨酸结合以产生 (+)-放线菌素。该方法的模块化开启了模拟合成的新可能性。
• Oxazolidinone compounds and method of using the same as a vasodilator
  申请人：Sankyo Company, Ltd.

  公开号：US05356918A1

  公开（公告）日：1994-10-18

  Compounds of formula (I): ##STR1## wherein W represents an oxygen atom and X represents a group of formula --N(R.sup.1)--; R.sup.1 is hydrogen, alkyl or aralkyl; R.sub.2 and R.sup.3 are each hydrogen, alkyl, aralkyl, aryl or aromatic heterocyclic; R.sup.4 is hydrogen, alkyl or aralkyl; and A is alkylene which is optionally substituted by carboxy; and pharmaceutically acceptable salts and esters thereof, have a valuable vasodilatory activity.

  公式（I）的化合物：##STR1## 其中W代表氧原子，X代表公式--N（R.sup.1）-的基团; R.sup.1是氢，烷基或芳基烷基; R.sub.2和R.sup.3分别是氢，烷基，芳基烷基，芳基或芳香族杂环; R.sup.4是氢，烷基或芳基烷基; A是可选地取代羧基的烷基;以及其药学上可接受的盐和酯，具有有价值的血管扩张活性。
• Iodocyclization of the (tolylsulfonyl)- and (trichloroacetyl)carbamates of secondary .alpha.-allenic alcohols. Highly diastereoselective synthesis of syn-1,2-amino alcohols and trans-5-alkyl-1-oxo-2-oxazolidine-4-carboxylic acids
  作者：Richard W. Friesen、Aleksandra E. Kolaczewska

  DOI：10.1021/jo00016a016

  日期：1991.8

  The iodocyclization of tosyl- and (trichloroacetyl)carbamates 9 and 10, respectively, of secondary alpha-allenic alcohols is described. The cyclofunctionalization reactions are highly diastereoselective, providing trans-5-alkyl-4-(1-iodoethylene)-2-oxazolidinones 11 and 12 as the major diastereomers in ratios of 6.3:1 to > 99: < 1. The mechanism of cyclization involves the initial formation of diiodides resulting from the addition of I2 to the terminal olefin of the allene moiety, followed by a kinetically controlled intramolecular SN2' displacement of iodide. Hydrolysis and acetylation of the N-tosyloxazolidinones 11 provide syn-1,2-amino alcohol derivatives 15. Alternatively, ozonolysis of the vinyl iodides derived from the cyclization of the (trichloroacetyl)carbamates 12 provides a novel, efficient, and highly diastereoselective route to trans-5-alkyl-2-oxazolidinone-4-carboxylic acids 25 and esters 26.