(S)-2-phenylbutyramide | 13490-76-1

• 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: (S)-2-phenylbutyramide
• 英文别名: (S)-2-phenyl-butyric acid amide；(S)-2-Phenyl-buttersaeure-amid；D-2-Phenyl-butyramid；(S)-(+)-α-Ethyl-phenylacetamid；2-Phenylbutyramide, (+)-；(2S)-2-phenylbutanamide
• CAS: 13490-76-1
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: UNFGQCCHVMMMRF-VIFPVBQESA-N

物化性质

• 沸点：
  316.8±21.0 °C(Predicted)
• 密度：
  1.040±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-2-phenylbutyramide 在 dimethyl sulfide borane 、 盐酸 、 甲醇 、 水 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 以70%的产率得到(2S)-2-苯基丁烷-1-胺
  参考文献：
  名称：

  WO2008/79759

  摘要：

  公开号：
• 作为产物：
  描述：

  2-苯基丁酸 在 ammonium hydroxide 、 R(+)-alpha-甲基苄胺 、 水 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 (S)-2-phenylbutyramide
  参考文献：
  名称：

  Synthesis of chiral disulfides: potential reagents for enantioselective sulfurization

  摘要：

  Synthesis of chiral phosphorothioates for use as antisense oligonucleotides might benefit from the use of chiral disulfides. This paper reports the synthesis of chiral analogs of phenylacetyl disulfide and of 5-methyl-3H-1,2,4-dithiazol-3-one from the same set of 2-arylalkanoic acids. The X-ray crystal structures of the disulfides derived from (R) and [S]-2-phenylpropanoic acid establish the stereochemistry and the helicity of these materials, and density functional theory calculations suggest that the high specific rotations can be due to preferred retention of this helicity in solution. Chiral HPLC showed that the final products were formed with enantiomeric purities from 86.1% to99.9%. [image omitted].

  DOI：

  10.1080/17415993.2011.580346

文献信息

• Probing the enantioselectivity of a diverse group of purified cobalt-centred nitrile hydratases
  作者：S. van Pelt、M. Zhang、L. G. Otten、J. Holt、D. Y. Sorokin、F. van Rantwijk、G. W. Black、J. J. Perry、R. A. Sheldon

  DOI：10.1039/c0ob01067g

  日期：——

  In this study a diverse range of purified cobalt containing nitrile hydratases (NHases, EC 4.2.1.84) from Rhodopseudomonas palustris HaA2 (HaA2), Rhodopseudomonas palustris CGA009 (009), Sinorhizobium meliloti 1021 (1021), and Nitriliruptor alkaliphilus (iso2), were screened for the first time for their enantioselectivity towards a broad range of chiral nitriles. Enantiomeric ratios of >100 were found for the NHases from HaA2 and CGA009 on 2-phenylpropionitrile. In contrast, the Fe-containing NHase from the well-characterized Rhodococcus erythropolis AJ270 (AJ270) was practically aselective with a range of different α-phenylacetonitriles. In general, at least one bulky group in close proximity to the α-position of the chiral nitriles seemed to be necessary for enantioselectivity with all NHases tested. Nitrile groups attached to a quaternary carbon atom were only reluctantly accepted and showed no selectivity. Enantiomeric ratios of 80 and >100 for AJ270 and iso2, respectively, were found for the pharmaceutical intermediate naproxennitrile, and 3-(1-cyanoethyl)benzoic acid was hydrated to the corresponding amide by iso2 with an enantiomeric ratio of >100.

  在本研究中，首次对来自红假单胞菌HaA2（HaA2）、红假单胞菌CGA009（009）、豌豆根瘤菌1021（1021）和嗜碱氮裂解菌（iso2）的多种纯化钴含氮裂解酶（NHases，EC 4.2.1.84）对一系列手性腈的立体选择性进行了筛选。对于2-苯基丙腈，来自HaA2和CGA009的NHases的立体异构比大于100。相比之下，来自已知红球菌AJ270（AJ270）的含铁NHase对一系列不同α-苯基乙腈实际上没有选择性。总的来说，对于所有测试的NHases来说，似乎至少需要一个在α-位附近的大体积基团才能实现立体选择性。连接在四级碳原子上的腈基团仅勉强被接受，并且没有显示出选择性。对于药物中间体萘普生腈，AJ270和iso2的立体异构比分别为80和大于100；iso2还将3-（1-氰乙基）苯甲酸水合为相应的酰胺，立体异构比大于100。
• [EN] SUBSTITUTED PYRIDINES AS INHIBITORS OF DNMT1<br/>[FR] PYRIDINES SUBSTITUÉES EN TANT QU'INHIBITEURS DE DNMT1
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2017216726A1

  公开（公告）日：2017-12-21

  The invention is directed to substituted pyridine derivatives. Specifically, the invention is directed to compounds according to Formula (Iar): (Iar) wherein Yar, X1ar, X2ar, R1ar, R2ar, R3ar, R4ar and R5ar are as defined herein; or a pharmaceutically acceptable salt or prodrug thereof. The compounds of the invention are selective inhibitors of DNMT1 and can be useful in the treatment of cancer, pre-cancerous syndromes, beta hemoglobinopathy disorders, sickle cell disease, sickle cell anemia, and beta thalassemia, and diseases associated with DNMT1 inhibition. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting DNMT1 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  该发明涉及取代吡啶衍生物。具体而言，该发明涉及符合以下式（Iar）的化合物：（Iar）其中Yar、X1ar、X2ar、R1ar、R2ar、R3ar、R4ar和R5ar如本文所定义；或其药学上可接受的盐或前药。该发明的化合物是DNMT1的选择性抑制剂，可用于治疗癌症、癌前综合征、β血红蛋白病、镰状细胞病、镰状细胞贫血、β地中海贫血以及与DNMT1抑制相关的疾病。因此，该发明进一步涉及包含该发明化合物的药物组合物。该发明还进一步涉及使用该发明化合物或包含该发明化合物的药物组合物抑制DNMT1活性和治疗相关疾病的方法。
• PRIMIDONE PROCESS AND COMPOSITIONS
  申请人：Sajja Eswaraiah

  公开号：US20070149779A1

  公开（公告）日：2007-06-28

  The present invention relates to a process for the preparation of primidone. It also relates to compositions comprising primidone of desired particle size distribution, processes for the preparation of such particles and processes for the preparation of the compositions.

  本发明涉及一种制备普鲁米酮的方法。它还涉及包含所需粒度分布的普鲁米酮的组合物，制备这些粒子的过程以及制备这些组合物的过程。
• Absolute Configuration and Polymorphism of 2-Phenylbutyramide and α-Methyl-α-phenylsuccinimide
  作者：Victor N. Khrustalev、Bhupinder Sandhu、Samuel Bentum、Alexandr Fonari、Arcadius V. Krivoshein、Tatiana V. Timofeeva

  DOI：10.1021/cg500284q

  日期：2014.7.2

  Crystal structures of racemic and homochiral forms of 2-phenylbutyramide (1) and 3-methyl-3-phenylpyrrolidine-2,5-dione (2) were investigated in detail by a single crystal X-ray diffraction study. Absolute configurations of the homochiral forms of 1 and 2, obtained by chromatographic separation of racemates, were determined. It was revealed that racemate and homochiral forms of 1 are very similar in

  通过单晶X射线衍射研究详细研究了2-苯基丁酰胺（1）和3-甲基-3-苯基吡咯烷-2,5-二酮（2）的外消旋和同手性形式的晶体结构。确定了通过外消旋物的色谱分离获得的1和2的纯手性形式的绝对构型。据透露，外消旋体和纯手性形式1是在超分子组织（H-粘合带）在晶体，红外（IR）光谱特性，和熔点方面非常相似。以1的同手性形式存在两种不同的分子构象可以模拟外消旋体中H键结合的带的晶体堆积1。对于化合物2的同手性形式，发现了两个非常相似的H键合之字形样链的两个多晶型物修饰物（单斜晶和正交晶），其晶体结构，IR光谱和熔点与2的外消旋形式均存在显着差异。与化合物1不同，化合物2的手性形式具有比相应的外消旋体更高的密度，这与Wallach规则相矛盾，并且表明在这种情况下，手性形式比外消旋体形式更稳定。
• Proteasome inhibitors and methods of using the same
  申请人：Bernadini Raffaella

  公开号：US20050107307A1

  公开（公告）日：2005-05-19

  The present invention provides boronic acid compounds, boronic esters, and compositions thereof that can modulate apoptosis such as by inhibition of proteasome activity. The compounds and compositions can be used in methods of inducing apoptosis and treating diseases such as cancer and other disorders associated directly of indirectly with proteasome activity.

  本发明提供了硼酸化合物、硼酸酯及其组合物，可以通过抑制蛋白酶体活性等方式调节细胞凋亡。这些化合物和组合物可以用于诱导细胞凋亡并治疗癌症等疾病，以及与蛋白酶体活性直接或间接相关的其他疾病。