(S)-(+)-3,4,4-trimethyl-2-pentanone | 133524-14-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(+)-3,4,4-trimethyl-2-pentanone
• 英文别名: 2-Pentanone, 3,4,4-trimethyl-, (S)-(9CI)；(3S)-3,4,4-trimethylpentan-2-one
• CAS: 133524-14-8
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: RAQLTZBGPDCFJW-ZCFIWIBFSA-N

物化性质

• 沸点：
  139.9±8.0 °C(Predicted)
• 密度：
  0.810±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,1-二氯甲醚 、 <(1S)-1,2,2-trimethylpropyl>methoxymethylborane 在 双氧水 、 lithium tert-butoxide 作用下， 生成 (S)-(+)-3,4,4-trimethyl-2-pentanone
  参考文献：
  名称：

  Chiral synthesis via organoboranes. 30. Facile synthesis, by the Matteson asymmetric homologation procedure, of .alpha.-methyl boronic acids not available from asymmetric hydroboration and their conversion into the corresponding aldehydes, ketones, carboxylic acids, and amines of high enantiomeric purity

  摘要：

  2-(alpha-Methylalkyl)- or 2-(alpha-arylethyl)-1,3,2-dioxaborinanes, RMeHC*BO2(CH2)3 (R = alkyl or aryl), of very high enantiomeric purity, not available from asymmetric hydroboration, can be prepared by the Matteson asymmetric homologation procedure of optically pure pinanediol or 2,3-butanediol boronate esters with (dichloromethyl)lithium, LiCHCl2, conveniently generated in situ in THF at -78-degrees-C, followed by reaction with either a Grignard reagent or an alkyllithium, with subsequent removal of the chiral auxiliaries. alpha-Methyl boronic esters thus obtained are readily converted into the corresponding aldehydes by the reaction with [methoxy(phenylthio)methyl]lithium [LiCH(OMe)SPh] (MPML) and mercuric chloride, followed by oxidation with hydrogen peroxide in a pH 8 buffer medium. The two-phase aqueous chromic acid procedure can be used to oxidize these aldehydes to the corresponding alpha-methyl carboxylic acids of very high enantiomeric purity without significant racemization. Additionally, pinanediol or 2,3-butanediol alpha-methylorganylboronate esters can be conveniently converted into borinic ester derivatives, RMeHC*BMe(OMe), of very high enantiomeric purity by reaction with methyllithium, followed by treatment with methanolic hydrogen chloride and subsequent recovery of the valuable chiral auxiliaries. These borinic ester derivatives are converted into alpha-methyl ketones and alpha-methyl primary amines of known absolute configuration by the alpha,alpha-dichloromethyl methyl ether (DCME) reaction and the reaction with hydroxylamine-O-sulfonic acid, respectively. The present synthesis of chiral 2-organyl-1,3,2-dioxaborinanes by the Matteson route, together with our direct asymmetric hydroboration procedure, makes it possible to synthesize many chiral boronic acid derivatives in very high enantiomeric purities. These complementary procedures greatly expand the scope of asymmetric synthesis via chiral organoboranes.

  DOI：

  10.1021/jo00010a022

文献信息

• [EN] DERIVATIVES OF 1-[(CYCLOPENTYL OR 2-PYRROLIDINYL)CARBONYLAMINOMETHYL]-4-(1,3-THIAZOL-5-YL) BENZENE WHICH ARE USEFUL FOR THE TREATMENT OF PROLIFERATIVE, AUTOIMMUNE OR INFLAMMATORY DISEASES<br/>[FR] DÉRIVÉS DE 1-[(CYCLOPENTYL OU 2-PYRROLIDINYL)CARBONYLAMINOMÉTHYL]-4-(1,3-THIAZOL-5-YL)-BENZÈNE QUI SONT UTILES POUR LE TRAITEMENT DE MALADIES PROLIFÉRATIVES, AUTO-IMMUNES OU INFLAMMATOIRES
  申请人：UNIV DUNDEE

  公开号：WO2016146985A1

  公开（公告）日：2016-09-22

  There is provided novel small molecule E3 ubiquitin ligase protein binding ligand compounds, having utility in PROteolysis Targeted Chimeras (PROTACs), as well as processes for the preparation thereof, and use in medicine. There is particularly provided PROTACs which bind to a protein within the bromo- and Extra-terminal (BET) family of proteins, and especially to PROTACs including novel small molecule E3 ubiquitin ligase protein binding ligand compounds which selectively induce degradation of the BRD4 protein within the bromodomain of the BET family of proteins.

  提供了新型小分子E3泛素连接酶蛋白结合配体化合物，适用于蛋白质降解靶向嵌合物（PROTACs），以及其制备过程和在医学中的用途。特别提供了能够结合到溴-和额外末端（BET）蛋白家族中的蛋白质的PROTACs，尤其是包括新型小分子E3泛素连接酶蛋白结合配体化合物的PROTACs，其选择性诱导BET蛋白家族中溴结构域内的BRD4蛋白降解。
• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2017023631A1

  公开（公告）日：2017-02-09

  The present disclosure is generally directed to antiviral compounds, and more specifically directed to combinations of compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such combinations, and methods for inhibiting the function of the NS5A protein.

  本公开涉及抗病毒化合物，更具体地涉及可以抑制由丙型肝炎病毒（HCV）编码的NS5A蛋白功能的化合物组合，包括这种组合的组成物，以及抑制NS5A蛋白功能的方法。
• NOVEL ANTIVIRAL AGENTS AGAINST HBV INFECTION
  申请人：DREXEL UNIVERSITY

  公开号：US20160024004A1

  公开（公告）日：2016-01-28

  The present invention provides novel compounds of formula (I) and methods of use thereof. In certain embodiments, the compounds of the invention are useful as nucleocapsid assembly inhibitors. In other embodiments, the compounds of the invention are useful as pregenomic RNA encapsidation inhibitors of Hepatitis B virus (HBV). In yet other embodiments, the compounds of the invention are useful for the treatment of viral infection, including HBV and related viral infections.

  本发明提供了式(I)的新化合物及其使用方法。在某些实施例中，本发明的化合物可用作核衣壳组装抑制剂。在其他实施例中，本发明的化合物可用作乙型肝炎病毒（HBV）的前基因组RNA包装抑制剂。在其他实施例中，本发明的化合物可用于治疗病毒感染，包括HBV和相关病毒感染。
• Spirocyclic inhibitors of serine proteases for the treatment of hcv infections
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP2631238A1

  公开（公告）日：2013-08-28

  The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt thereof. These compounds inhibit serine protease, particularly the hepatitis C virus NS3-NS4A protease.

  本发明涉及式（I）化合物或其药学上可接受的盐。这些化合物可抑制丝氨酸蛋白酶，特别是丙型肝炎病毒 NS3-NS4A 蛋白酶。
• HEPATITIS C VIRUS INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP1505963B1

  公开（公告）日：2011-04-20