N-[(1R)-1-benzyl-2-hydroxyethyl]acetamide | 52485-50-4

• 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: N-[(1R)-1-benzyl-2-hydroxyethyl]acetamide
• 英文别名: (R)-N-(1-hydroxy-3-phenylpropan-2-yl)acetamide；N-acetyl-D-phenylalaninol；D-N-Acetylphenylalaninol；N-[(2R)-1-hydroxy-3-phenylpropan-2-yl]acetamide
• CAS: 52485-50-4
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: OKDZNDUPIRUYLF-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(1R)-1-benzyl-2-hydroxyethyl]acetamide 在 盐酸 、 N,N'-羰基二咪唑 作用下， 以 氯仿 、 水 、 乙酸乙酯 为溶剂， 生成 (R)-2-acetamido-3-phenylpropyl D-phenylalaninate
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of asperphenamate derivatives as autophagy inducer

  摘要：

  In an effort to improve the aqueous solubility and the antitumor activity of natural product asperphenamate, we have designed and synthesized three series of asperphenamate derivatives, including series I (simplifying molecular skeleton series), series II (introducing a hydroxyl group to A-phenyl ring series) and series III (disrupting molecular planarity series). All derivatives have displayed a significantly increased solubility compared with asperphenamate. Their growth inhibitory activities in vitro were screened by the standard MTT method in MCF-7, HeLa, and BEL-7402 cell lines. With the exception of the derivatives in series I, most of derivatives in series II and series III showed growth inhibitory activity. Among all derivatives, IM23b in series III showed the greatest potency in human breast cancer MCF-7 cells. The cellular potency of IM23b was approximately 1.5-fold more potent than that of cisplatin. The mechanism of cell death induced by IM23b in human breast cancer MCF-7 cells was further investigated. We concluded that the cell death was induced by autophagy instead of apoptosis or cell cycle arrest. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.101
• 作为产物：
  描述：

  N-(3-oxo-1-phenylprop-1-en-2-yl)acetamide 在 氢气 、 [Rh((R,R)-QuinoxP*)(cod)]SbF₆ 作用下， 以 乙酸乙酯 为溶剂， 30.0 ℃ 、3.0 MPa 条件下， 反应 24.0h， 以99%的产率得到N-[(1R)-1-benzyl-2-hydroxyethyl]acetamide
  参考文献：
  名称：

  手性α-酰胺基醛及其制备方法

  摘要：

  本发明涉及一种手性α‑酰胺基醛及其制备方法，所述方法包括以下步骤：下述通式(1)表示的α‑脱氢酰胺基醛在双膦‑铑配合物催化作用下，在有机溶剂中与氢气发生还原反应得到下述通式(2)表示的手性α‑酰胺基醛化合物。本合成路线采用不对称催化氢化的方法，工艺简单高效绿色，非常适合于工业化大批量生产。产物手性酰胺基醛可进一步衍生为手性配体和手性药物中间体。

  公开号：

  CN112047856B

文献信息

• AMINOPYRIDINE AND CARBOXYPYRIDINE COMPOUNDS AS PHOSPHODIESTERASE 10 INHIBITORS
  申请人：Allen Jennifer R.

  公开号：US20100160280A1

  公开（公告）日：2010-06-24

  Pyridine and pyrimidine compounds: or a pharmaceutically acceptable salt thereof, wherein m, n, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , and Y are as defined in the specification; or a pharmaceutically acceptable salt thereof, wherein ring A, m, n, y, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , X 1 , X 2 , and ring A are as defined in the specification; and or a pharmaceutically acceptable salt thereof, wherein m, n, y, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 9 , X 1 , X 2 , and ring A are as defined in the specification; compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

  吡啶和嘧啶化合物： 或者是根据说明书中定义的药用可接受盐，其中m、n、R1、R2、R3、R4、R5、R6、R7、X1、X2、X3、X4、X5、X6、X7、X8和Y都有所定义； 或者是根据说明书中定义的药用可接受盐，其中环A、m、n、y、R2、R3、R4、R5、R6、R7、R8、R9、X1、X2和环A都有所定义； 或者是根据说明书中定义的药用可接受盐，其中m、n、y、R2、R3、R4、R5、R6、R7、R9、X1、X2和环A都有所定义；含有它们的组合物以及制备这类化合物的方法。还提供了通过抑制PDE10治疗可治疗的疾病或病症的方法，例如肥胖、非胰岛素依赖型糖尿病、精神分裂症、双相情感障碍、强迫症等。
• Nanomole-Scale Assignment of Configuration for Primary Amines Using a Kinetic Resolution Strategy
  作者：Shawn M. Miller、Renzo A. Samame、Scott D. Rychnovsky

  DOI：10.1021/ja310620c

  日期：2012.12.19

  The absolute configurations of primary amines were assigned using a kinetic resolution strategy with Mioskowski's enantioselective 1-(R,R) and 2-(S,S) acylating agents. A simple mnemonic was developed to determine the configuration. A pseudoenantiomeric pair of reagents, 1-(R,R) and 2-(S,S)-d(3), was prepared and used to assay primary amines on a micromolar scale. The ESI-MS readout of the resulting

  使用 Mioskowski 的对映选择性 1-(R,R) 和 2-(S,S) 酰化剂的动力学拆分策略指定伯胺的绝对构型。开发了一个简单的助记符来确定配置。制备了一对假对映体试剂 1-(R,R) 和 2-(S,S)-d(3)，并用于在微摩尔级测定伯胺。所得乙酰胺产物的 ESI-MS 读数再现了动力学实验中的选择性因素。该方法可用于胺的混合物，并已用小至 50 nmol 的胺样品进行了验证。
• PYRIDINE AND PYRIMIDINE DERIVATIVES AS PHOSPHODIESTERASE 10 INHIBITORS
  申请人：Allen Jennifer R.

  公开号：US20100125062A1

  公开（公告）日：2010-05-20

  Pyridine and pyrimidine compounds, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

  吡啶和嘧啶化合物，以及含有它们的组合物，以及制备这些化合物的方法。本文还提供了治疗通过抑制PDE10可治疗的疾病或疾病的方法，如肥胖症、非胰岛素依赖型糖尿病、精神分裂症、躁郁症、强迫症等。
• [EN] COMPOUNDS HAVING BETA-AGONIST ACTIVITY<br/>[FR] COMPOSES PRESENTANT UNE ACTIVITE BETA-AGONISTE
  申请人：PFIZER LTD

  公开号：WO2005092841A1

  公开（公告）日：2005-10-06

  The invention relates to compounds of formula (1) and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such derivatives. The compounds according to the present invention are useful in numerous diseases, disorders and conditions, in particular inflammatory, allergic and respiratory diseases, disorders and conditions.

  本发明涉及化合物的公式（1）以及用于制备、制备中间体、含有和使用这些衍生物的过程。根据本发明的化合物在许多疾病、紊乱和情况中有用，特别是炎症性、过敏性和呼吸道疾病、紊乱和情况。
• Chemo‐ and Enantioselective Hydrogenation of α‐Formyl Enamides: An Efficient Access to Chiral α‐Amido Aldehydes
  作者：Jian Zhang、Jia Jia、Xincheng Zeng、Yuanhao Wang、Zhenfeng Zhang、Ilya D. Gridnev、Wanbin Zhang

  DOI：10.1002/anie.201905263

  日期：2019.8.12

  effectively synthesize chiral α‐amino aldehydes, which have a wide range of potential applications in organic synthesis and medicinal chemistry, a highly chemo‐ and enantioselective hydrogenation of α‐formyl enamides has been developed, catalyzed by a rhodium complex of a P‐stereogenic bisphosphine ligand. Under different hydrogen pressures, the chiral α‐amido aldehydes and β‐amido alcohols were obtained

  为了有效合成在有机合成和药物化学中具有广泛潜在应用的手性α-氨基醛，已开发出一种高化学和对映选择性的α-甲酰胺基氢化反应，该反应由P的铑配合物催化立体异构双膦配体。在不同的氢气压力下，获得的手性α-酰胺醛和β-氨基醇的收率高（97-99％），并且具有出色的化学选择性和对映选择性（ee高达> 99.9％  ）。氢化反应可以以克为单位进行，并具有高的底物/催化剂比（最高20000 S / C），并且氢化的产物被进一步转化为几种重要的手性产物。催化循环的计算给出了R /的清晰描述。S途径为对映选择性提供了合理的解释，并揭示了其他几个具体特征。