(R)-2-hydroxy-2,4-dimethylpentanoic acid | 135415-91-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-2-hydroxy-2,4-dimethylpentanoic acid
• 英文别名: (2R)-2-hydroxy-2,4-dimethylpentanoic acid
• CAS: 135415-91-7
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: CWMPKCMFWTVVMX-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲基-2-戊酮 在 盐酸 作用下， 以 异丙醚 为溶剂， 反应 61.0h， 生成 (R)-2-hydroxy-2,4-dimethylpentanoic acid
  参考文献：
  名称：

  Enzyme-catalyzed synthesis or (R)-ketone-cyanohydrins and their hydrolysis to (R)-α-hydroxy-α-methyl-carboxylic acids

  摘要：

  (R)-Ketone-cyanohydrins (R)-2 are obtained with high enantioselectivity from aliphatic ketones 1 and HCN in organic solvents using (R)-oxynitrilase (EC 4.1.2.10) as catalyst. Acid catalyzed hydrolysis of the cyanohydrins (R)-2 affords the corresponding (R)-alpha-hydroxy-alpha-methyl-carboxylic acids (R)-3 without measurable racemization.

  DOI：

  10.1016/s0040-4039(00)78796-x

文献信息

• [EN] N-(PYRID-4-YL)AMIDES AND N-(PYRIMIDIN-4-YL)AMIDES AND THEIR PHARMACEUTICAL AND COSMETIC USE<br/>[FR] N-(PYRID-4-YL)AMIDES ET N-(PYRIMIDIN-4-YL)AMIDES ET LEUR UTILISATION PHARMACEUTIQUE ET COSMÉTIQUE
  申请人：GALDERMA RES & DEV

  公开号：WO2013064681A1

  公开（公告）日：2013-05-10

  The present invention relates generally to the field of pharmaceuticals and cosmetics. More specifically, the present invention pertains to certain N-(pyrid-4-yl)amides and N-(pyrimidin-4-yl)amides of formula (1) which are potent modulators (e.g., inhibitors) of an androgen receptor, and which are useful, for example, in therapy, for example, in the treatment of a dermatological disease or disorder; a disease or disorder of the sebaceous gland(s); acne; hyperseborrhoea; oily skin; seborrhoeic dermatitis; hyperpilosity or hirsutism; atopic dermatitis; or androgenic alopecia; especially acne. The present invention also relates to compositions (e.g., pharmaceutical compositions, cosmetic compositions) comprising the compounds; methods of preparing the compositions; methods of modulating (e.g., inhibiting) an androgen receptor using the compounds and/or compositions; and medical and/or cosmetic use of the compounds and compositions.

  本发明一般涉及制药和化妆品领域。更具体地，本发明涉及某些式（1）的N-(吡啶-4-基)酰胺和N-(嘧啶-4-基)酰胺，这些化合物是雄激素受体的有效调节剂（例如，抑制剂），在治疗中很有用，例如，在治疗皮肤病或紊乱；皮脂腺的疾病或紊乱；痤疮；皮脂过多；油性皮肤；脂溢性皮炎；多毛症或多毛症；特应性皮炎；或雄激素性脱发；尤其是痤疮。本发明还涉及包含这些化合物的组合物（例如，制药组合物，化妆品组合物）；制备这些组合物的方法；使用这些化合物和/或组合物调节（例如，抑制）雄激素受体的方法；以及这些化合物和组合物的医学和/或化妆用途。
• Process Development and Crystallization in Oiling-Out System of a Novel Topical Antiandrogen
  作者：Sébastien Daver、Nicolas Rodeville、Francois Pineau、Jean-Marie Arlabosse、Christine Moureou、Franck Muller、Romain Pierre、Karinne Bouquet、Laurence Dumais、Jean-Guy Boiteau、Isabelle Cardinaud

  DOI：10.1021/acs.oprd.6b00392

  日期：2017.2.17

  formation using phosphorus(V) oxybromide followed by mono SNAr reaction with sodium methoxide and a final Hofmann rearrangement. Enantiopure α-hydroxy-acid 6 was obtained using an enantioselective cyanosilylation followed by salt resolution with (S)-α-methyl benzylamine. The absolute configuration of compound 1 was determined with anomalous scattering and the final crystallization of API was performed

  描述了一种获得新的局部抗雄激素的（S）-N-（2-溴-6-甲氧基吡啶-4-基）-2-羟基-2,4-二甲基戊酰胺1的有效途径。目标化合物已由公斤规模生产，从citrazinic acid的总收率达25％（HPLC纯度为98.8％，ee > 99％ee）。使用临时保护基团促进氨基吡啶4和α-羟基酸6之间的关键酰胺偶联，以促进酰氯的形成。氨基吡啶4由市售的citrazinic acid通过溴化磷（V）溴化二溴化物，然后用单核苷S N制备而成。Ar与甲醇钠反应，最后进行霍夫曼重排。使用对映选择性氰基硅烷化，然后用（S）-α-甲基苄基胺进行盐拆分，得到对映纯α-羟基酸6。化合物1的绝对构型是通过反常散射确定的，API的最终结晶是在晶种温度低于单晶温度下进行晶种注入后得到的，其结晶粉末呈“沙漠玫瑰”形团簇。
• Fused-Aromatic Compounds Having Anti-Diabetic Activity
  申请人：Wood Harold B.

  公开号：US20080194586A1

  公开（公告）日：2008-08-14

  Fused aromatic compounds of Formula (I) are PPAR gamma agonists or partial agonists and are useful in the treatment or control of type II diabetes, including hyperglycemia, dylipidermia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, and obesity that are often associated with type 2 diabetes.

  公式（I）的融合芳香化合物为PPAR-gamma激动剂或部分激动剂，可用于治疗或控制II型糖尿病，包括常与II型糖尿病相关的高血糖，血脂异常，高脂血症，高胆固醇血症，高甘油三酯血症和肥胖症。
• N-(PYRID-4-YL)AMIDES AND N-(PYRIMIDIN-4-YL)AMIDES AND THEIR PHARMACEUTICAL AND COSMETIC USE
  申请人：GALDERMA RESEARCH & DEVELOPMENT

  公开号：US20140234245A1

  公开（公告）日：2014-08-21

  N-(pyrid-4-yl)amides and N-(pyrimidin-4-yl)amides of formula (1) are described that are potent modulators (e.g., inhibitors) of an androgen receptor, and which are useful, for example, in the treatment of a dermatological disease or disorder; a disease or disorder of the sebaceous gland(s); acne; hyperseborrhoea; oily skin, seborrhoeic dermatitis; hyperpilosity or hirsutism; atopic dermatitis; or androgenic alopecia; especially acne. Also described, are compositions (e.g., pharmaceutical compositions, cosmetic compositions) comprising the compounds; methods of preparing the compositions; methods of modulating (e.g., inhibiting) and androgen receptors using the compounds and/or compositions; and medical and/or cosmetic use of the compounds and compositions.

  本文描述了公式（1）的N-（吡啶-4-基）酰胺和N-（嘧啶-4-基）酰胺，它们是雄激素受体的有效调节剂（例如抑制剂），并且在治疗皮肤病或紊乱，皮脂腺疾病或紊乱；痤疮；多油性皮肤，脂溢性皮炎；多毛或多发性毛发；特别是痤疮方面非常有用。还描述了包含这些化合物的组合物（例如制药组合物，化妆品组合物），制备这些组合物的方法，使用这些化合物和/或组合物调节（例如抑制）雄激素受体的方法，以及这些化合物和组合物的医疗和/或化妆品用途。
• Diastereomerenreine Zwischenprodukte und ihre Verwendung bei der Herstellung von (R)- oder (S)-Ketoprofen
  申请人：BAYER AG

  公开号：EP0531700A2

  公开（公告）日：1993-03-17

  Die Erfindung betrifft neue diastereomerenreine Ester des Ketoprofens, Verfahren Zu ihrer Herstellung durch asymmetrische Keten-Addition und ihre Verwendung bei der Herstellung von (R)- oder (S)-Ketoprofen.

  本发明涉及新的非对映异构纯酯酮洛芬、通过不对称烯酮加成法制备它们的工艺，以及它们在制备(R)-或(S)-酮洛芬中的用途。