2-hydroxy-N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]benzamide | 941299-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxy-N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]benzamide
• CAS: 941299-49-6
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: IBGLVNLLGXQXNR-ZDUSSCGKSA-N

物化性质

• 沸点：
  535.1±50.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]benzamide 在 potassium carbonate 、 臭氧 、 sodium iodide 作用下， 以 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 丙酮 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  同心圆内酯的不对称合成

  摘要：

  已经开发出一种从水杨酸合成 (-)- 和 (+)- 同心圆内酯的实用策略。该方法的关键特征是与醛的顺序芳族锂化和缩合，醛由 L- 或 D-苯丙醇衍生的手性恶唑啉单元引导，用作助剂。

  DOI：

  10.1002/ejoc.201403604
• 作为产物：
  描述：

  水杨酸 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 32.5h， 生成 2-hydroxy-N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]benzamide
  参考文献：
  名称：

  β-Hydroxyamide derivatives of salicylic acid as organocatalysts for enantioselective reductions of prochiral ketones

  摘要：

  In order to find the most effective catalyst for the enantioselective reduction of a prochiral ketone, a series of novel beta-hydroxyamide derivatives of salicylic acid and chiral amino alcohols were synthesized. Different substituted prochiral ketones have been reduced in high yield (up to 99%) and the corresponding secondary alcohols are formed with good enantiomeric excess (up to 86%). The mechanism of this type of catalyst can be explained by considering the reaction mechanism for the CBS catalyst. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.016
• 作为试剂：
  描述：

  2,2,2-三氟苯乙酮 在 dimethylsulfide borane complex 、 2-hydroxy-N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]benzamide 作用下， 以 四氢呋喃 为溶剂， 以7%的产率得到
  参考文献：
  名称：

  β-Hydroxyamide derivatives of salicylic acid as organocatalysts for enantioselective reductions of prochiral ketones

  摘要：

  In order to find the most effective catalyst for the enantioselective reduction of a prochiral ketone, a series of novel beta-hydroxyamide derivatives of salicylic acid and chiral amino alcohols were synthesized. Different substituted prochiral ketones have been reduced in high yield (up to 99%) and the corresponding secondary alcohols are formed with good enantiomeric excess (up to 86%). The mechanism of this type of catalyst can be explained by considering the reaction mechanism for the CBS catalyst. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.016

文献信息

• Plasminogen Activator Inhibitor-1 Inhibitors
  申请人：Trifonov Latchezar S.

  公开号：US20080280920A1

  公开（公告）日：2008-11-13

  Inhibitors of plasminogen activator inhibitor-1 (PAI-I) are provided, which may also act as anti cancer agents, of formulae (I-V).

  提供了抑制纤溶酶原激活剂抑制剂-1（PAI-I）的抑制剂，这些抑制剂也可以作为抗癌剂，其化学式为（I-V）。
• β-Hydroxyamide derivatives of salicylic acid as organocatalysts for enantioselective reductions of prochiral ketones
  作者：Yılmaz Turgut、Murat Azizoglu、Aslı Erdogan、Nevin Arslan、Halil Hosgoren

  DOI：10.1016/j.tetasy.2013.05.016

  日期：2013.7

  In order to find the most effective catalyst for the enantioselective reduction of a prochiral ketone, a series of novel beta-hydroxyamide derivatives of salicylic acid and chiral amino alcohols were synthesized. Different substituted prochiral ketones have been reduced in high yield (up to 99%) and the corresponding secondary alcohols are formed with good enantiomeric excess (up to 86%). The mechanism of this type of catalyst can be explained by considering the reaction mechanism for the CBS catalyst. (C) 2013 Elsevier Ltd. All rights reserved.
• Asymmetric Synthesis of Concentricolide
  作者：Xiaojing Liu、Lingling Hu、Lizhen Jiang、Junhao Jia、Di Zhang、Xiaochuan Chen

  DOI：10.1002/ejoc.201403604

  日期：2015.4

  A practical strategy for the synthesis of both (–)- and (+)-concentricolide from salicylic acid has been developed. The key feature of the approach is sequential aromatic lithiation and condensation with an aldehyde directed by a chiral oxazoline unit derived either from L- or D-phenylalaninol, which is employed as an auxiliary.

  已经开发出一种从水杨酸合成 (-)- 和 (+)- 同心圆内酯的实用策略。该方法的关键特征是与醛的顺序芳族锂化和缩合，醛由 L- 或 D-苯丙醇衍生的手性恶唑啉单元引导，用作助剂。