(+)-(4R)-4-[(tert-butoxycarbonyl)amino]pentan-2-one | 869468-34-8

• 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: (+)-(4R)-4-[(tert-butoxycarbonyl)amino]pentan-2-one
• 英文别名: Carbamic acid, [(1R)-1-methyl-3-oxobutyl]-, 1,1-dimethylethyl ester；tert-butyl N-[(2R)-4-oxopentan-2-yl]carbamate
• CAS: 869468-34-8
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: LINWYTPTURMUAO-SSDOTTSWSA-N

物化性质

• 沸点：
  299.2±23.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(4R)-4-[(tert-butoxycarbonyl)amino]pentan-2-one 在 potassium hypochlorite 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (3R)-3-[[(1,1-二甲基乙炔氧基)羰基]氨基]-丁酸
  参考文献：
  名称：

  3-[2-((2S)-2-Cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-3-methyl-butyramide analogues as selective DPP-IV inhibitors for the treatment of type-II diabetes

  摘要：

  Based on the structures of NVP-DPP728 (1) and NVP-LAF237 (Vildagliptin, 2), three series of DPP-IV inhibitors were synthesized by linking substituted anilines, benzylamines, and phenylethylamines to (2S)-cyanopyrrolidine through a linker. More than 20 compounds were evaluated for their in vitro DPP-IV inhibition and selectivity profile over DPP-II, DPP8, and FAP enzymes. Selected compounds 5f and 7i showed in vivo plasma DPP-IV inhibition and inhibited glucose excursion in OGTT after oral administration in Wistar rats. Compound 5f (DPP-1V IC50 = 116 nM) has the potential for development as antidiabetic agent. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.019
• 作为产物：
  描述：

  (3R)-3-[[(1,1-二甲基乙炔氧基)羰基]氨基]-丁酸 在 1-丙基磷酸酐 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 (+)-(4R)-4-[(tert-butoxycarbonyl)amino]pentan-2-one
  参考文献：
  名称：

  [EN] REVERSIBLE MACROCYCLIC KINASE INHIBITORS
  [FR] INHIBITEURS DE KINASE RÉVERSIBLES MACROCYCLIQUES

  摘要：

  The present invention relates to macrocyclic compounds and compositions containing said compounds acting as kinase inhibitors. Moreover, the present invention provides processes for the preparation of the disclosed compounds, as well as methods of using them, for instance as a medicament, in particular for the treatment specific kinase mediated disorders, such as cancer.

  公开号：

  WO2023110936A1

文献信息

• (<i>S</i>,<i>S</i>)-(<i>+</i>)-Pseudoephedrine as Chiral Auxiliary in Asymmetric Aza-Michael Reactions. Unexpected Selectivity Change when Manipulating the Structure of the Auxiliary
  作者：Juan Etxebarria、Jose L. Vicario、Dolores Badia、Luisa Carrillo、Nerea Ruiz

  DOI：10.1021/jo051207j

  日期：2005.10.1

  the structure of the chiral auxiliary, which has allowed a diastereodivergent procedure to be set up for performing asymmetric aza-Michael reactions using the same chirality source. Finally, the adducts obtained in the asymmetric aza-Michael reaction have proven to be very versatile synthetic intermediates in the preparation of other interesting compounds such as β-amino esters, γ-amino alcohols, and

  金属苄酰胺与手性氨基醇衍生的α，β-不饱和酰胺的不对称aza-Michael反应（S，S）-（+）-伪麻黄碱已被详细研究。已经对最重要的实验参数（溶剂，温度，亲核体结构，添加剂的影响）进行了深入研究，表明该反应通常以良好的收率和非对映选择性进行，尽管必须根据取代条件修改实验条件共轭受体的模式。另外，在操纵手性助剂的结构时，观察到非常有趣的面部选择性反转，这允许建立非对映发散程序，以使用相同的手性来源进行不对称的aza-Michael反应。最后，
• 3-[2-((2S)-2-Cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-3-methyl-butyramide analogues as selective DPP-IV inhibitors for the treatment of type-II diabetes
  作者：Mohane Selvaraj Coumar、Chung-Nien Chang、Chiung-Tong Chen、Xin Chen、Chia-Hui Chien、Ting-Yueh Tsai、Jai-Hong Cheng、Hsin-Yi Wu、Chia-Hung Han、Ssu-Hui Wu、Yu-Wen Huang、Tsu Hsu、Li-Jen Hsu、Yu-Sheng Chao、Hsing-Pang Hsieh、Weir-Torn Jiaang

  DOI：10.1016/j.bmcl.2006.12.019

  日期：2007.3

  Based on the structures of NVP-DPP728 (1) and NVP-LAF237 (Vildagliptin, 2), three series of DPP-IV inhibitors were synthesized by linking substituted anilines, benzylamines, and phenylethylamines to (2S)-cyanopyrrolidine through a linker. More than 20 compounds were evaluated for their in vitro DPP-IV inhibition and selectivity profile over DPP-II, DPP8, and FAP enzymes. Selected compounds 5f and 7i showed in vivo plasma DPP-IV inhibition and inhibited glucose excursion in OGTT after oral administration in Wistar rats. Compound 5f (DPP-1V IC50 = 116 nM) has the potential for development as antidiabetic agent. (c) 2006 Elsevier Ltd. All rights reserved.
• [EN] REVERSIBLE MACROCYCLIC KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE RÉVERSIBLES MACROCYCLIQUES
  申请人：[en]NETHERLANDS TRANSLATIONAL RESEARCH CENTER HOLDING B.V

  公开号：WO2023110936A1

  公开（公告）日：2023-06-22

  The present invention relates to macrocyclic compounds and compositions containing said compounds acting as kinase inhibitors. Moreover, the present invention provides processes for the preparation of the disclosed compounds, as well as methods of using them, for instance as a medicament, in particular for the treatment specific kinase mediated disorders, such as cancer.