(R)-N-phenyl-2-methylbutanamide | 105497-45-8

• 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: (R)-N-phenyl-2-methylbutanamide
• 英文别名: 2-methyl-N-phenylbutanamide；(R)-2-methyl-butyric acid anilide；(R)-2-Methyl-buttersaeure-anilid；(2R)-2-methyl-N-phenylbutanamide
• CAS: 105497-45-8
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: YQRDADVUUPKUBC-SECBINFHSA-N

物化性质

• 沸点：
  330.8±11.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• 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：

  (R)-2-甲基丁酸 生成 (R)-N-phenyl-2-methylbutanamide
  参考文献：
  名称：

  Schroeder et al., Chemische Berichte, 1959, vol. 92, p. 2338,2362

  摘要：

  DOI：

文献信息

• Asymmetric Markovnikov Hydroaminocarbonylation of Alkenes Enabled by Palladium-Monodentate Phosphoramidite Catalysis
  作者：Ya-Hong Yao、Hui-Yi Yang、Ming Chen、Fei Wu、Xing-Xing Xu、Zheng-Hui Guan

  DOI：10.1021/jacs.0c11249

  日期：2021.1.13

  n of alkenes with anilines has been developed for the atom-economical synthesis of 2-substituted propanamides bearing an α-stereocenter. A novel phosphoramidite ligand L16 was discovered which exhibited very high reactivity and selectivity in the reaction. This asymmetric Markovnikov hydroaminocarbonylation employs readily available starting materials and tolerates a wide range of functional groups

  已经开发了钯催化的烯烃与苯胺的不对称马尔科夫尼科夫氢氨基羰基化反应，用于原子经济合成带有 α-立体中心的 2-取代丙酰胺。发现了一种新的亚磷酰胺配体 L16，它在反应中表现出非常高的反应性和选择性。这种不对称 Markovnikov 氢氨基羰基化使用容易获得的起始材料并耐受范围广泛的官能团，从而为在环境条件下区域选择性和对映选择性合成 2-取代丙酰胺提供了一种简便而直接的方法。机理研究表明，该反应通过钯氢化物途径进行。
• Selective androgen receptor degrader (SARD) ligands and methods of use thereof
  申请人：GTx, Inc.

  公开号：US10017471B2

  公开（公告）日：2018-07-10

  This invention provides novel indole, indazole, benzimidazole, indoline, quinolone, isoquinoline, and carbazole selective androgen receptor degrader (SARD) compounds, pharmaceutical compositions and uses thereof in treating prostate cancer, advanced prostate cancer, castration resistant prostate cancer, other AR-expressing cancers, androgenic alopecia or other hyper androgenic dermal diseases, Kennedy's disease, amyotrophic lateral sclerosis (ALS), abdominal aortic aneurysm (AAA), and uterine fibroids, and to methods for reducing the levels (through degradation) and/or activity (through inhibition) of any androgen receptor including androgen receptor-full length (AR-FL) including pathogenic and/or resistance mutations, AR-splice variants (AR-SV), and pathogenic polyglutamine (polyQ) polymorphisms of AR in a subject.

  本发明提供了新型吲哚、吲唑、苯并咪唑、吲哚啉、喹诺酮、异喹啉和咔唑选择性雄激素受体降解剂（SARD）化合物、药物组合物及其在治疗前列腺癌、晚期前列腺癌、阉割耐药前列腺癌、其他表达AR的癌症、雄激素性脱发或其他高雄激素性皮肤病、肯尼迪病、肌萎缩性脊髓侧索硬化症（ALS）、腹主动脉瘤（AAA）和子宫肌瘤中的用途，以及降低其水平（通过降解）的方法、肌萎缩性脊髓侧索硬化症（ALS）、腹主动脉瘤（AAA）和子宫肌瘤，以及降低受试者体内任何雄激素受体的水平（通过降解）和/或活性（通过抑制）的方法，包括雄激素受体全长（AR-FL），包括致病性和/或抗性突变、AR-剪接变体（AR-SV）和致病性多谷氨酰胺（polyQ）多态性。
• Selective androgen receptor degrader (SARD) Ligands and methods of use thereof
  申请人：GTx, Inc.

  公开号：US10441570B2

  公开（公告）日：2019-10-15

  This invention provides novel indole, indazole, benzimidazole, benzotriazole, indoline, quinolone, isoquinoline, and carbazole selective androgen receptor degrader (SARD) compounds, pharmaceutical compositions and uses thereof in treating hyperproliferations of the prostate including pre-malignancies and benign prostatic hyperplasia, prostate cancer, advanced prostate cancer, castration resistant prostate cancer, other AR-expressing cancers, androgenic alopecia or other hyper androgenic dermal diseases, Kennedy's disease, amyotrophic lateral sclerosis (ALS), abdominal aortic aneurysm (AAA), and uterine fibroids, and to methods for reducing the levels (through degradation) and/or activity (through inhibition) of any androgen receptor including androgen receptor-full length (AR-FL) including pathogenic and/or resistance mutations, AR-splice variants (AR-SV), and pathogenic polyglutamine (polyQ) polymorphisms of AR in a subject.

  本发明提供了新型吲哚、吲唑、苯并咪唑、苯并三唑、吲哚啉、喹诺酮、异喹啉和咔唑选择性雄激素受体降解剂（SARD）化合物、药物组合物及其在治疗前列腺过度增生（包括恶性肿瘤前期和良性前列腺增生）、前列腺癌、晚期前列腺癌、阉割抵抗性前列腺癌、其他AR表达癌症中的用途、雄激素性脱发或其他高雄激素性皮肤病、肯尼迪病、肌萎缩性脊髓侧索硬化症（ALS）、腹主动脉瘤（AAA）和子宫肌瘤、以及降低受试者体内包括雄激素受体全长（AR-FL）在内的任何雄激素受体的水平（通过降解）和/或活性（通过抑制）的方法，包括致病性和/或抗性突变、AR-剪接变体（AR-SV）和致病性多聚谷氨酰胺（polyQ）多态性。
• Enantioselective inclusion of amide guests into a chiral N,N′-ditrityl amino amide host to compensate the loss of hydrogen bonds broken by installation of trityl groups
  作者：Ken Megumi、Shohei Yokota、Shoji Matsumoto、Motohiro Akazome

  DOI：10.1016/j.tetlet.2012.12.029

  日期：2013.2

  A new crystalline N,N'-ditrityl amino amide host included several amide guests in the host cavity to form inclusion crystals. Although the installation of trityl groups into (S)-2-aminopropanamide broke its inherent hydrogen bonds of amide groups, inclusion of guest amides compensated the loss of hydrogen bonds. X-ray crystallography showed that these inclusion cavities and host-guest interactions such as hydrogen bonds, van der Waals interaction, and CH center dot center dot center dot O interactions play important roles for highly enantioselective inclusion. The enantiomeric inclusion was 67% ee (S-form) for N-phenyl 2-methylbutanamide, 82% ee (S-form) for N-phenyl 2-chlorobutanamide, and 83% ee (S-form) for N-phenyl 2-bromobutanamide. (c) 2012 Elsevier Ltd. All rights reserved.
• SELECTIVE ANDROGEN RECEPTOR DEGRADER (SARD) LIGANDS AND METHODS OF USE THEREOF
  申请人：GTx, Inc.

  公开号：US20170029370A1

  公开（公告）日：2017-02-02

  This invention provides novel indole, indazole, benzimidazole, indoline, quinolone, isoquinoline, and carbazole selective androgen receptor degrader (SARD) compounds, pharmaceutical compositions and uses thereof in treating prostate cancer, advanced prostate cancer, castration resistant prostate cancer, other AR-expressing cancers, androgenic alopecia or other hyper androgenic dermal diseases, Kennedy's disease, amyotrophic lateral sclerosis (ALS), abdominal aortic aneurysm (AAA), and uterine fibroids, and to methods for reducing the levels (through degradation) and/or activity (through inhibition) of any androgen receptor including androgen receptor-full length (AR-FL) including pathogenic and/or resistance mutations, AR-splice variants (AR-SV), and pathogenic polyglutamine (polyQ) polymorphisms of AR in a subject.