(alphaS)-alpha-(1-甲基乙基)苯乙酸 | 13490-69-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (alphaS)-alpha-(1-甲基乙基)苯乙酸
• 中文别名: (αS)-α-异丙基苯乙酸；(αS)-α-(1-甲基乙基)苯乙酸；(ALPHAS)-ALPHA-(1-甲基乙基)苯乙酸
• 英文名称: (S)-2-phenyl-3-methylbutyric acid
• 英文别名: (S)-(+)-2-phenyl-3-methylbutyric acid；(S)-(+)-α-isopropylphenylacetic acid；(S)-(+)-2-isopropyl-2-phenylacetic acid；(S)-(+)-3-methyl-2-phenylbutyric acid；(S)-(+)-2-isopropylphenylacetic acid；(S)-2-isopropyl-2-phenylacetic acid；(S)-3-methyl-2-phenylbutanoic acid；(2S)-3-methyl-2-phenylbutanoic acid
• CAS: 13490-69-2
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: HDLQGISFYDYWFJ-JTQLQIEISA-N

物化性质

• 熔点：
  86-88℃
• 沸点：
  105 °C(Press: 0.1 Torr)
• 密度：
  1.063

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H315,H317,H319,H335
• 储存条件：
  室温下应存放在干燥密封的容器中。

反应信息

• 作为反应物：
  描述：

  (alphaS)-alpha-(1-甲基乙基)苯乙酸 在 palladium on activated charcoal 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 (S)-(+)-N-羟基-4-(3-甲基-2-苯基丁酰氨基)苯甲酰胺
  参考文献：
  名称：

  Structure-Based Optimization of Phenylbutyrate-Derived Histone Deacetylase Inhibitors

  摘要：

  Previously, we developed a strategy to develop a novel class of histone deacetylase (HDAC) inhibitors by tethering short-chain fatty acids with Zn2+-chelating motifs, which led to N-hydroxy-4-(4-phenylbutyryl-amino)benzamide (HTPB), a hydroxamate-tethered phenylbutyrate derivative with sub-micromolar potency in inhibiting HDAC activity and cancer cell proliferation. In this study, we carried out structure-based optimization of HTPB by using the framework generated by the structure of histone deacetylase-like protein (HDLP)-trichostatin A (TSA) complexes. Docking of HTPB into the HDLP binding domain suggested that the hydrophobic microenvironment encompassed by Phe-198 and Phe-200 could be exploited for structural optimization. This premise was corroborated by the greater potency of (S)-(+)-N-hydroxy-4-(3-methyl-2-phenylbutyrylamino)-benzamide [(S)-11] (IC50 in HDAC inhibition, 16 nM), of which the isopropyl moiety was favorable in interacting with this hydrophobic motif. (S)-11 at concentrations as low as 0.1 mu M was effective in causing histone hyperacetylation and p21(WAF/CIP1) overexpression and suppressing proliferation in cancer cells.

  DOI：

  10.1021/jm0503749
• 作为产物：
  描述：

  3-甲基-2-苯基丁-2-烯酸 在 (R)-N-methyl-N-<2-(4-morpholino)ethyl>-<1-(S)-1',2-bis(diphenylphosphino)ferrocenyl>ethylamine 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 30.0h， 生成 (alphaS)-alpha-(1-甲基乙基)苯乙酸
  参考文献：
  名称：

  Asymmetric hydrogenation of trisubstituted acrylic acids catalyzed by a chiral (aminoalkyl)ferrocenylphosphine-rhodium complex

  摘要：

  DOI：

  10.1021/ja00259a043

文献信息

• [EN] PYRROLOPYRIDAZINE JAK3 INHIBITORS AND THEIR USE FOR THE TREATMENT OF INFLAMMATORY AND AUTOIMMUNE DISEASES<br/>[FR] INHIBITEURS DE JAK3 DE TYPE PYRROLOPYRIDAZINE ET LEUR UTILISATION POUR TRAITER LES MALADIES INFLAMMATOIRES ET AUTO-IMMUNES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2012125887A1

  公开（公告）日：2012-09-20

  Disclosed are compounds of formula (I) and pharmaceutically acceptable salts thereof. The compounds of formula (I) inhibit tyrosine kinase activity of JAK3, thereby making them useful for the treatment of inflammatory and autoimmune diseases.

  揭示了式（I）的化合物及其药用盐。式（I）的化合物抑制JAK3的酪氨酸激酶活性，因此它们可用于治疗炎症和自身免疫性疾病。
• Chiral α-Substituted Carbonyls and Alcohols from the S_N2‘ Displacement of Cuprates on Chiral Carbonates:  An Alternative to the Alkylation of Chiral Enolates
  作者：Claude Spino、Christian Beaulieu、Julie Lafrenière

  DOI：10.1021/jo000810t

  日期：2000.10.1

  A highly stereoselective sequence of reactions, based on the anti-selective S(N)2' addition of cuprates to allylic carbonates, transforms alkynes or alkenyl halides into carbonyls having alpha-chiral centers. The method, which uses menthone as a chiral auxiliary, is a useful alternative to the alkylation of chiral enolates with the added advantage of allowing for the "alkylation" of sec- and tert-alkyl

  基于铜酸盐向烯丙基碳酸酯的抗选择性S（N）2'加成，高度立体选择性的反应序列将炔烃或烯基卤化物转化为具有α-手性中心的羰基。该方法使用薄荷酮作为手性助剂，是手性烯醇盐烷基化的一种有用的替代方法，具有允许仲烷基和叔烷基和芳基“烷基化”的额外优点。
• Magnesium Tetraarylporphyrin Tweezer:  a CD-Sensitive Host for Absolute Configurational Assignments of α-Chiral Carboxylic Acids
  作者：Gloria Proni、Gennaro Pescitelli、Xuefei Huang、Koji Nakanishi、Nina Berova

  DOI：10.1021/ja036294g

  日期：2003.10.1

  alpha-chiral carboxylic acids based on a modified circular dichroic (CD) exciton chirality method has been developed. The protocol relies on a host-guest complexation mechanism: the chiral substrates are derivatized to give bifunctional amide conjugates ("guests") that form complexes with a dimeric magnesium porphyrin host, Mg-T (T stands for "tweezer") that acts as a "receptor". The two porphyrins in the

  已经开发了一种基于改进的圆形二向色 (CD) 激子手性方法确定 α-手性羧酸绝对构型的协议。该协议依赖于宿主 - 客体复合机制：手性底物被衍生化以产生双功能酰胺偶联物（“客体”），与二聚镁卟啉宿主 Mg-T（T 代表“镊子”）形成复合物，作为一个“受体”。复合物中的两个卟啉根据它们的空间尺寸（根据构象能 A 值分配）采用由手性中心的取代基决定的优选螺旋度，因此，根据所研究的底物的绝对构型。这种手性方法，用各种手性底物验证，已被证明是可靠且普遍适用的，包括具有复杂结构的天然产品。选定的主客体复合物的分子建模、核磁共振和 FTIR 实验揭示了底物与镁卟啉物质的连接模式，并阐明了复合物的结构。当氧官能团直接连接到手性中心时，CD 对偶的符号与根据空间尺寸预测的符号相反。核磁共振和分子模拟实验表明，这种明显的不一致是由于客体分子的构象特征造成的。立体化学分析被证明是一种灵敏的技术，不仅用于确定底物
• Renin inhibiting compounds
  申请人：Hoffmann-La Roche Inc.

  公开号：US05250517A1

  公开（公告）日：1993-10-05

  Compounds which are amino acid derivatives and have the formula ##STR1## in which R.sup.1 is hydrogen or methyl, R.sup.2 is ethyl, propyl or imidazol-4-yl, R.sup.3 is isobutyl, cyclohexylmethyl or benzyl, and A is defined as herein are useful as renin inhibitors.

  具有以下结构式的氨基酸衍生物化合物，其中R.sup.1是氢或甲基，R.sup.2是乙基、丙基或咪唑-4-基，R.sup.3是异丁基、环己甲基或苄基，以及A的定义如本文所述，可用作肾素抑制剂。
• Determination of the Absolute Configuration of β-Chiral Primary Alcohols Using the Competing Enantioselective Conversion Method
  作者：Alexander S. Burns、Alexander J. Wagner、Jennifer L. Fulton、Kyle Young、Armen Zakarian、Scott. D. Rychnovsky

  DOI：10.1021/acs.orglett.7b01189

  日期：2017.6.2

  A method for determining the absolute configuration of β-chiral primary alcohols has been developed. Enantioenriched alcohols were acylated in the presence of either enantiomer of the enantioselective acylation catalyst HBTM, and the faster reaction was determined by measuring product conversion using 1H NMR spectroscopic analysis. An empirical mnemonic was developed that correlates the absolute configuration

  已经开发出确定β-手性伯醇的绝对构型的方法。在对映选择性酰化催化剂HBTM的任何一种对映异构体的存在下，将富含对映体的醇酰化，并通过使用1 H NMR光谱分析测量产物转化率来确定更快的反应。开发了经验助记符，其将醇的绝对构型与更快反应的催化剂相关联。该方法成功的底物包括在立体异构中心带有“指导基团”的伯醇。指导基团包括芳烃，杂芳烃，烯酮和卤化物。