甲基3-甲基-D-异缬氨酸酯 | 107246-36-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 甲基3-甲基-D-异缬氨酸酯
• 中文别名: 2-甲基-3-(苯基硫烷基)吡嗪
• 英文名称: (S)-α-methyl-valine methyl ester
• 英文别名: (S)-α-Methylvalin-methylester；H-L-(αMe)Val-OMe；(S)-2-Amino-2,3-dimethylbutanoic acid methyl ester；methyl (2S)-2-amino-2,3-dimethylbutanoate
• CAS: 107246-36-6
• 化学式: C₇H₁₅NO₂
• 分子量: 145.202
• InChiKey: OQQLWOQWKDIFEB-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基3-甲基-D-异缬氨酸酯 在 N-羟基-7-氮杂苯并三氮唑 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 二乙胺 作用下， 以 甲苯 为溶剂， 生成 cyclo[TOAC-L-(αMe)Val]
  参考文献：
  名称：

  Nitroxyl Peptides as Catalysts of Enantioselective Oxidations

  摘要：

  The achiral, nitroxyl-containing a-amino acid TOAC (TOAC 2,2,6,6-tetramethylpiperidine-1-oxyl-4-amino-4-carboxylic acid), in combination with the chiral alpha-amino acid C-alpha-methyl valine [(alphaMe)Val]. was used to prepare short peptides (from di- to hexa-) that induced the enantioselective oxidation of racemic I-phenylethanol to acetophenone. The best catalyst was an N-alpha-acylated dipeptide alkylamide with the -TOAC-(alphaMe)Val- sequence folded in a stable, intramolecularly hydrogen-bonded beta-turn conformation with large. lipophilic (hydrophobic) N- and C-terminal blocking groups. We rationalized our findings by proposing models for the diastereomeric intermediates between (R)-[and (S)]-1-phenylethanol and the catalyst Fmoc-TOAC-L(alphaMe)Val-NHiPr, based on the X-ray diffraction structure of the latter.

  DOI：

  10.1002/1521-3765(20020104)8:1<84::aid-chem84>3.0.co;2-n
• 作为产物：
  描述：

  methyl (S)-2-(((1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylidene)amino)-3-methylbutanoate 在 柠檬酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 90.25h， 生成 甲基3-甲基-D-异缬氨酸酯
  参考文献：
  名称：

  手性席夫碱的烷基化和质子化：非对映选择性作为反应物性质的函数

  摘要：

  报道了控制由2-羟基pinan-3-one和α-氨基酯制备的手性席夫碱的非对映选择性烷基化和质子化反应的因素：酯，烷基化剂和碱的性质。

  DOI：

  10.1016/s0040-4020(01)86467-x

文献信息

• [EN] INHIBITORS OF PLK<br/>[FR] INHIBITEURS DE PLK
  申请人：CHROMA THERAPEUTICS LTD

  公开号：WO2009141575A1

  公开（公告）日：2009-11-26

  Compounds of formula (I) are PLK inhibitors, useful for the treatment of cell proliferative diseases wherein R1 is hydrogen, or an optionally substituted (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl or (C3-C6)cycloalkyl group; R2 is hydrogen, or an optionally substituted (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl or (C3-C6)cycloalkyl group; R3 is hydrogen, -CN, hydroxyl, halogen, optionally substituted (C1C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl or (C3-C6)cycloalkyl, -NR6R7 or C1-C4 alkoxy, wherein R6 and R7 are independently hydrogen or optionally substituted (C1C6)alkyl; ring A is an optionally substituted mono- or bi-cyclic carbocyclic or heterocyclic ring or a ring system having up to 12 ring atoms; T is a radical of formula (II) wherein R4 is a carboxylic acid group (-COOH), or an ester group which is hydrolysable by one or more intracellular esterase enzymes to a carboxylic acid group; R5 and R15 independently represent the side chain of a natural or non-natural alpha amino acid but neither of R5 and R15 is hydrogen, or R5 and R15 taken together with the carbon atom to which they are attached form a C3-C7 cycloalkyl ring; and Y, L1 and X1 are as defined in the claims.

  式(I)的化合物是PLK抑制剂，用于治疗细胞增殖性疾病，其中R1是氢，或者是一个可选择取代的(C1-C6)烷基，(C2-C6)烯基，(C2-C6)炔基或(C3-C6)环烷基；R2是氢，或者是一个可选择取代的(C1-C6)烷基，(C2-C6)烯基，(C2-C6)炔基或(C3-C6)环烷基；R3是氢，-CN，羟基，卤素，可选择取代的(C1C6)烷基，(C2-C6)烯基，(C2-C6)炔基或(C3-C6)环烷基，-NR6R7或C1-C4烷氧基，其中R6和R7分别独立地是氢或可选择取代的(C1C6)烷基；环A是一个可选择取代的单环或双环碳环或杂环，或者是一个具有最多12个环原子的环系统；T是式(II)中的基团，其中R4是一个羧酸基(-COOH)，或者是一个可被一个或多个胞内酯酶水解为羧酸基的酯基；R5和R15独立地代表天然或非天然α-氨基酸的侧链，但R5和R15中的任何一个都不是氢，或者R5和R15与它们连接的碳原子一起形成一个C3-C7环烷基环；Y，L1和X1如权利要求中所定义。
• Diastereoselective synthesis of quaternary α-amino acids from diketopiperazine templates
  作者：Stephen G. Davies、A. Christopher Garner、Jaqueline V. A. Ouzman、Paul M. Roberts、Andrew D. Smith、Emma J. Snow、James E. Thomson、Juan A. Tamayo、Richard J. Vickers

  DOI：10.1039/b704475e

  日期：——

  Sequential enolate alkylations of (S)-N(1)-methyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one and (S)-N(1)-p-methoxybenzyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one proceed with excellent levels of diastereoselectivity (>90% de) affording quaternary α-amino acids in high enantiomeric excess (>98% ee) after deprotection and hydrolysis.

  (S)-N(1)-甲基-5-甲氧基-6-异丙基-3,6-二氢吡嗪-2-酮和(S)-N(1)-对甲氧基苄基-5-甲氧基-6-异丙基-3,6-二氢吡嗪-2-酮的顺序对映体烷基化反应以极好的非对映选择性（>90% de）进行，以高对映体过量（>90% de）得到季δ-氨基酸、6- 二氢嗪-2-酮的非对映选择性极佳（de>90%），在脱保护和水解后可得到对映体过量（ee>98%）的季δ-氨基酸。
• Schoellkopf, Ulrich; Hartwig, Wolfgang; Groth, Ulrich, Liebigs Annalen der Chemie, 1981, # 4, p. 696 - 708
  作者：Schoellkopf, Ulrich、Hartwig, Wolfgang、Groth, Ulrich、Westphalen, Karl-Otto

  DOI：——

  日期：——
• ENDOPHYTIC STREPTOMYCETES FROM HIGHER PLANTS WITH BIOLOGICAL ACTIVITY
  申请人：Strobel A. Gary

  公开号：US20070190633A1

  公开（公告）日：2007-08-16

  The present invention relates to isolated strains of a Streptomyces spp. which are endophytes of dicotyledonous plants and to methods for selecting such strains. The present invention also relates to compounds having biological activity selected from the group consisting of munumbicin A, munumbicin B, munumbicin C and munumbicin D, kakadumycin A, kakadumycin B, and kakadumycin C. The present invention further relates to compositions of such compounds and to methods of protecting plants against attack by a plant pathogen and methods of inhibiting bacterial growth, fungal growth, viral infection, growth of parasitic organisms, and cancer cell growth with such compositions.
• US7259004B1
  申请人：——

  公开号：US7259004B1

  公开（公告）日：2007-08-21