(1S,2R)-N-(2-phenylcyclopropyl)acetamide | 1164475-05-1

• 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: (1S,2R)-N-(2-phenylcyclopropyl)acetamide
• 英文别名: (1S,2R)-(+)-N-acetyltranylcypromine；N-Acetyl-trans-2-phenylcyclopropylamin；N-[(1S,2R)-2-phenylcyclopropyl]acetamide
• CAS: 1164475-05-1
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: OKNYZIGDRLPEEJ-MNOVXSKESA-N

物化性质

• 沸点：
  365.1±22.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (1S,2S)-2-Phenyl-cyclopropanecarbonyl azide 以 溶剂黄146 为溶剂， 生成 (1S,2R)-N-(2-phenylcyclopropyl)acetamide
  参考文献：
  名称：

  Youssef, Abdel-Hamid A.; Sharaf, Saber M.; Abdel-Baki, Samy A., Journal fur praktische Chemie (Leipzig 1954), 1982, vol. 324, # 3, p. 491 - 497

  摘要：

  DOI：

文献信息

• CYTOKINE INHIBITORS
  申请人：Boman Erik

  公开号：US20100093734A1

  公开（公告）日：2010-04-15

  The present invention provides low molecular weight compounds useful as cytokine inhibitors, and compositions thereof. In particular, compounds of the invention are useful as anti-inflammatory agents. There are further provided methods for the preparation of such agents and their use in preventing or treating conditions mediated by cytokines such as arthritis.

  本发明提供了低分子量化合物，可用作细胞因子抑制剂及其组合物。特别是，本发明的化合物可用作抗炎剂。还提供了制备这种药剂的方法，以及其在预防或治疗由细胞因子介导的疾病，如关节炎方面的用途。
• Cytokine inhibitors
  申请人：Boman Erik

  公开号：US20050107399A1

  公开（公告）日：2005-05-19

  The present invention provides low molecular weight compounds useful as cytokine inhibitors, and compositions thereof. In particular, compounds of the invention are useful as anti-inflammatory agents. There are further provided methods for the preparation of such agents and their use in preventing or treating conditions mediated by cytokines such as arthritis.

  本发明提供了低分子量化合物，作为细胞因子抑制剂以及其组合物。特别地，本发明的化合物可用作抗炎剂。此外，还提供了制备这些药剂的方法，并将它们用于预防或治疗由细胞因子介导的疾病，例如关节炎。
• ALPHA-KETOAMIDES AND DERIVATIVES THEREOF
  申请人：Boman Erik

  公开号：US20100273797A1

  公开（公告）日：2010-10-28

  The present invention provides low molecular weight compounds useful as cytokine inhibitors, and compositions thereof. In particular, compounds of the invention are useful as anti-inflammatory agents. There are further provided methods for the preparation of such agents and their use in preventing or treating conditions medicated by cytokines such as arthritis.

  本发明提供了低分子量化合物，可用作细胞因子抑制剂及其组合物。特别地，本发明的化合物可用作抗炎剂。还提供了制备这些药剂的方法，并将其用于预防或治疗由细胞因子介导的疾病，例如关节炎。
• Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1 S ,2 R )-tranylcypromine
  作者：Tetsuya Ezawa、Yuya Kawashima、Takuya Noguchi、Seunghee Jung、Nobuyuki Imai

  DOI：10.1016/j.tetasy.2017.10.015

  日期：2017.12

  Primary amidations of carboxylic acids 1 or 3 with NH4Cl in the presence of ClCO2Et and Et3N were developed to afford the corresponding primary amides in 22% to quantitative yields. Additionally, we have applied the amidation to the preparation of various amides containing hydroxamic acids and achieved the synthesis of (1S,2R)-tranylcypromine as an antidepressant medicine via Lossen rearrangement. (C) 2017 Elsevier Ltd. All rights reserved.
• Enantioselective acylation of rac-2-phenylcycloalkanamines catalyzed by lipases
  作者：Javier González-Sabín、Vicente Gotor、Francisca Rebolledo

  DOI：10.1016/j.tetasy.2005.07.033

  日期：2005.9

  The kinetic resolution of some 2-phenylcycloalkanamines was performed by means of aminolysis reactions catalyzed by lipases, with Kazlauskas' rule being obeyed in all cases. The size of the ring and the stereochemistry of the stereogenic centers of the amines had a strong influence on both the enantiomeric ratio and the reaction rate of these aminolysis processes. Lipase B from Candida antarctica (CAL-B) showed excellent enantio selectivities toward trans-2-phenylcyclohexanamine in a variety of reaction conditions (E > 150), whereas lipase A from C antarctica (CAL-A) was the best catalyst for the acylation of cis-2-phenylcyclohexanamine (E = 34) and trans-2-phenylcyclopropanamine (E = 9). (C) 2005 Elsevier Ltd. All rights reserved.