2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid tert-butyl ester | 709656-07-5

• 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: 2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid tert-butyl ester
• 英文别名: 2-Phenyl-2-oxazoline-4-carboxylate tert-butyl ester；tert-butyl 2-phenyl-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 709656-07-5
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: NFTCCWULNGORJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid tert-butyl ester 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以98%的产率得到tert-butyl 2-benzamidoacrylate
  参考文献：
  名称：

  An unusual base-dependent α-alkylation and β-elimination of tert-butyl 2-phenyl-2-oxazoline-4-carboxylate: practical synthesis of (±)-α-alkylserines and tert-butyl benzamidoacrylate

  摘要：

  Practical synthesis of (+/-)-alpha-alkylserines and tert-butyl benzamidoacrylate from tert-butyl 2-phenyl-2-oxazoline-4-carboxylate (6) were developed. The alpha-alkylation and beta-elimination of 6 are dramatically dependent upon base conditions. The phase-transfer catalytic condition bearing solid KOH in toluene gives alpha-alkylation (up to >99%), and t-BuOK in DMF gives beta-elimination (98%). (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.03.041
• 作为产物：
  描述：

  methyl 2-phenyl-2-oxazoline-4-carboxylate 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 5.33h， 生成 2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  受保护的α-烷基羊毛硫氨酸衍生物的合成

  摘要：

  受保护的α-烷基羊毛硫氨酸衍生物从已知的苯恶唑啉前体开始以五个步骤合成。该方法涉及合成一个取代的环氨基磺酸盐家族，并通过受保护的半胱氨酸的亲核攻击使它们的区域选择性开放。这种有效的多步策略可高收率地提供各种α-烷基化羊毛硫氨酸衍生物。

  DOI：

  10.1016/j.tet.2014.05.004

文献信息

• Compositions for enhancing memory and methods therefor
  申请人：Baudry Michel

  公开号：US20060063707A1

  公开（公告）日：2006-03-23

  Compositions for enhancing memory of a subject comprising a combination of a positive modulator of an AMPA receptor and a positive modulator of an NMDA receptor are provided, wherein each modulator of the combination is present at a subtherapeutic dose for effecting memory enhancement. Methods for using such compositions in the treatment of cognitive impairment associated with aging, age-related diseases, and CNS disorders, for example, are provided. New fusion molecules are also provided that combine the positive modulator functionalities into one molecule.

  提供了用于增强主体记忆的组合物，包括AMPA受体的正调节剂和NMDA受体的正调节剂，其中组合物中的每种调节剂均以次治疗剂量存在，以实现记忆增强效果。提供了在治疗与衰老、与年龄相关的疾病和中枢神经系统疾病相关的认知障碍中使用这种组合物的方法。还提供了将正调节剂功能结合到一个分子中的新融合分子。
• METHOD FOR PRODUCING SERINE DERIVATIVE AND PROTEIN USED FOR THE SAME
  申请人：Kuroda Shinji

  公开号：US20100317068A1

  公开（公告）日：2010-12-16

  The present invention describes a method for generating a serine derivative and an optically active isomer thereof by a convenient technique, and an enzyme and the like useful in the method. In the presence of the following protein (A) and/or (B) having an enzymatic activity, an α-amino acid is reacted with an aldehyde to form a serine derivative: (A) a protein comprising the amino acid sequence of SEQ ID NO:5, and (B) a protein comprising an amino acid sequence of SEQ ID NO: 5, but which includes substitution, deletion, insertion and addition of one or more amino acids and is able to catalyze the reaction to form the serine derivative.

  本发明描述了一种通过方便的技术生成丝氨酸衍生物及其光学活性异构体的方法，以及在该方法中有用的酶等。在具有以下酶活性的蛋白质（A）和/或（B）的存在下，α-氨基酸与醛反应形成丝氨酸衍生物：（A）包含SEQ ID NO:5氨基酸序列的蛋白质，和（B）包含SEQ ID NO:5氨基酸序列，但包括一个或多个氨基酸的置换、删除、插入和添加，并能催化反应形成丝氨酸衍生物。
• Method for producing serine derivative and protein used for the same
  申请人：Kuroda Shinji

  公开号：US08372607B2

  公开（公告）日：2013-02-12

  The present invention describes a method for generating a serine derivative and an optically active isomer thereof by a convenient technique, and an enzyme and the like useful in the method. In the presence of the following protein (A) and/or (B) having an enzymatic activity, an α-amino acid is reacted with an aldehyde to form a serine derivative: (A) a protein comprising the amino acid sequence of SEQ ID NO:5, and (B) a protein comprising an amino acid sequence of SEQ ID NO: 5, but which includes substitution, deletion, insertion and addition of one or more amino acids and is able to catalyze the reaction to form the serine derivative.

  本发明描述了一种通过方便的技术生成丝氨酸衍生物及其光学活性异构体的方法，以及在该方法中有用的酶等。在具有以下酶活性的蛋白质(A)和/或(B)的存在下，α-氨基酸与醛反应形成丝氨酸衍生物：(A) 包含SEQ ID NO:5的氨基酸序列的蛋白质，以及(B) 包含SEQ ID NO:5的氨基酸序列，但包括一个或多个氨基酸的替换、缺失、插入和添加，并能够催化反应形成丝氨酸衍生物的蛋白质。
• Stereodivergent Construction of 1,4‐Nonadjacent Stereocenters via Hydroalkylation of Racemic Allylic Alcohols Enabled by Copper/Ruthenium Relay Catalysis
  作者：Xin Chang、Xiang Cheng、Xue‐Tao Liu、Cong Fu、Wei‐Yi Wang、Chun‐Jiang Wang

  DOI：10.1002/anie.202206517

  日期：2022.9.5

  catalysis has been developed. Merging the ruthenium-catalyzed asymmetric borrowing-hydrogen reaction with a copper-catalyzed asymmetric Michael addition into a one-pot procedure provided a route to highly functionalized δ-hydroxyesters bearing 1,4-nonadjacent stereocenters in good yields with excellent stereoselectivity under mild reaction conditions.

  通过双铜/钌中继催化，已经开发出一种前所未有的外消旋烯丙醇和外消旋酮亚胺酯的立体发散加氢烷基化反应。将钌催化的不对称借氢反应与铜催化的不对称迈克尔加成合并到一锅法中，提供了一种在温和反应条件下以良好的收率和优异的立体选择性制备具有 1,4-不相邻立体中心的高度官能化 δ-羟基酯的途径.
• Highly Enantioselective Synthesis of (<i>R</i>)-α-Alkylserines via Phase-Transfer Catalytic Alkylation of <i>o</i>-Biphenyl-2-oxazoline-4-carboxylic Acid <i>tert</i>-Butyl Ester Using <i>Cinchona</i>-Derived Catalysts
  作者：Yeon-Ju Lee、Jihye Lee、Mi-Jeong Kim、Taek-Soo Kim、Hyeung-geun Park、Sang-sup Jew

  DOI：10.1021/ol050228x

  日期：2005.4.14

  A highly enantioselective synthetic method for (R)-alpha-alkylserines was developed by the phase-transfer catalytic alkylation of o-biphenyl-2oxazoline-4-carboxylic acid tert-butyl ester (4i) using cinchona-derived phase-transfer catalyst N(1)-(9-anthracenylmethyl)-O(9)-allyi-dihydrocinchonidinium bromide (up to 96% ee).