2-甲基-2-丙基(2S)-2-乙酰氧基-3-甲基丁酸酯 | 380886-48-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-甲基-2-丙基(2S)-2-乙酰氧基-3-甲基丁酸酯
• 中文别名: (S)-2-乙酰氧基-3-甲基丁酸叔丁酯
• 英文名称: tert-butyl (S)-2-acetoxy-3-methylbutanoate
• 英文别名: (S)-tert-butyl 2-acetoxy-3-methylbutanoate；tert-butyl (2S)-2-acetyloxy-3-methylbutanoate
• CAS: 380886-48-6
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: MCHRBOFYIGYFPP-VIFPVBQESA-N

物化性质

• 沸点：
  256.3±13.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-2-丙基(2S)-2-乙酰氧基-3-甲基丁酸酯 在 potassium carbonate 、 1-羟基苯并三唑 、 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 D-tert-butyl 2-p-chlorophenylcarbonyl-aminoxy-3-methylbutanoate
  参考文献：
  名称：

  Synthesis and Characterization of Chiral N−O Turns Induced by α-Aminoxy Acids

  摘要：

  Chiral alpha -aminoxy acids of various side chains were synthesized with high optical purity starting from chiral alpha -amino acids. The conformations of diamides 13a-e, 15, and 16 were probed by using NMR, FT-IR, and CD spectroscopic methods as well as X-ray crystallography. The right-handed turns with eight-membered-ring intramolecular hydrogen bonds between adjacent residues (called the N-O turns) were found to be preferred for D-aminoxy acid residues, and they were independent of the side chains. The rigid chiral N-O turns should have great potential in molecular design.

  DOI：

  10.1021/jo010376a
• 作为产物：
  描述：

  L-缬氨酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 生成 2-甲基-2-丙基(2S)-2-乙酰氧基-3-甲基丁酸酯
  参考文献：
  名称：

  First Total Synthesis of Neoantimycin

  摘要：

  已成功完成新抗麦角菌素（1）的首次全合成，这是一种不寻常的抗麦角菌素类延环抗生素，采用分子内转酯化反应构建了15元环的四内酯核心。

  DOI：

  10.1246/cl.150509

文献信息

• Zinc‐Catalyzed Enantiospecific sp³–sp³ Cross‐Coupling of α‐Hydroxy Ester Triflates with Grignard Reagents
  作者：Christopher Studte、Bernhard Breit

  DOI：10.1002/anie.200800733

  日期：2008.7.7
• Mikhaleva,I.I. et al., Journal of general chemistry of the USSR, 1968, vol. 38, p. 1184 - 1193
  作者：Mikhaleva,I.I. et al.

  DOI：——

  日期：——
• N-i-Propoxy-N-biphenylsulfonylaminobutylhydroxamic acids as potent and selective inhibitors of MMP-2 and MT1-MMP
  作者：Armando Rossello、Elisa Nuti、Paolo Carelli、Elisabetta Orlandini、Marco Macchia、Susanna Nencetti、Maurizio Zandomeneghi、Federica Balzano、Gloria Uccello Barretta、Adriana Albini、Roberto Benelli、Giovanni Cercignani、Gillian Murphy、Aldo Balsamo

  DOI：10.1016/j.bmcl.2005.01.024

  日期：2005.3

  Structural manipulation of the pharmacophoric model of type A selective MMP inhibitors (MMPi), obtained by the insertion of some alkyl substituents R-2 possessing an appropriate geometry, steric bulkiness and lipophilicity, is able to improve potency, in the subnanomolar range on MMP-2, and to give a good MMP inhibition on MMP-14 (MT1-MMP) in the designed MMPi of type C, while maintaining a good MMP-1/MMP-2 selectivity profile. The simultaneous inhibition of these two enzymes yields type C compounds, which are potent antiangiogenic agents, able to block a chemoinvasion model on HUVEC cells in the micromolar range. (c) 2005 Elsevier Ltd. All rights reserved.
• Amber force field implementation, molecular modelling study, synthesis and MMP-1/MMP-2 inhibition profile of (R)- and (S)-N-hydroxy-2-(N-isopropoxybiphenyl-4-ylsulfonamido)-3-methylbutanamides
  作者：Tiziano Tuccinardi、Adriano Martinelli、Elisa Nuti、Paolo Carelli、Federica Balzano、Gloria Uccello-Barretta、Gillian Murphy、Armando Rossello

  DOI：10.1016/j.bmc.2006.01.056

  日期：2006.6

  Ab initio calculations (B3LYP/Lan12DZ level of theory) were performed in this study to determine all the structural and catalytic zinc parameters required in order to study MMPs and their complexes with hydroxamate inhibitors by means of the AMBER force field. The parameters thus obtained were used in order to study the docking of some known MMPi (Batimastat, CGS 27023A and. Prinomastat) and our previously described inhibitor a which had shown an inhibitory activity for MMP-1, and -2, with the aim of explaining the different selectivity. On this basis the two enantiomers (R)-b and (S)-b were designed and synthesized, as more potent MMP-2 inhibitors than our previously described inhibitor a. Between these two enantiomers the eutomer (R)-b proved to be 24.7 times and 15.3 times more potent than CGS 27023A and the parent compound a on MMP-2, maintaining a higher index of MMP-2/MMP-1 selectivity compared with CGS 27023A and the more potent inhibitor Prinomastat. The hydroxamate (R)-b can be considered as a progenitor of a new class of biphenylsulfonamido-based inhibitors that differ from compound a in the presence of an alkyl side chain on the C alpha atom, and show different potency and selectivity profiles on the two MMPs considered. (c) 2006 Elsevier Ltd. All rights reserved.