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(2R,3R)-diethyl 2-allyl-3-hydroxy-2-methylsuccinate | 1620219-03-5

中文名称
——
中文别名
——
英文名称
(2R,3R)-diethyl 2-allyl-3-hydroxy-2-methylsuccinate
英文别名
——
(2R,3R)-diethyl 2-allyl-3-hydroxy-2-methylsuccinate化学式
CAS
1620219-03-5
化学式
C12H20O5
mdl
——
分子量
244.288
InChiKey
JZMBSEMISBGGRP-JOYOIKCWSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    330.0±42.0 °C(predicted)
  • 密度:
    1.077±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    1.06
  • 重原子数:
    17.0
  • 可旋转键数:
    7.0
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.67
  • 拓扑面积:
    72.83
  • 氢给体数:
    1.0
  • 氢受体数:
    5.0

反应信息

  • 作为反应物:
    描述:
    (2R,3R)-diethyl 2-allyl-3-hydroxy-2-methylsuccinatesodium chloritesodium dihydrogenphosphate 、 lithium aluminium tetrahydride 、 2-甲基-2-丁烯 、 camphor-10-sulfonic acid 、 1-羟基苯并三唑戴斯-马丁氧化剂溶剂黄146盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺N,N-二异丙基乙胺 作用下, 以 四氢呋喃二氯甲烷丙酮 为溶剂, 反应 41.0h, 生成 (2R,3S)-2-hydroxy-3-(hydroxymethyl)-3-methyl-N-(3-oxo-3-(pentylamino)propyl)hex-5-enamide
    参考文献:
    名称:
    Stereochemical modification of geminal dialkyl substituents on pantothenamides alters antimicrobial activity
    摘要:
    Pantothenamides are N-substituted pantothenate derivatives which are known to exert antimicrobial activity through interference with coenzyme A (CoA) biosynthesis or downstream CoA-utilizing proteins. A previous report has shown that replacement of the ProR methyl group of the benchmark N-pentylpantothenamide with an allyl group (R-anti configuration) yielded one of the most potent antibacterial pantothenamides reported so far (MIC of 3.2 mu M for both sensitive and resistant Staphylococcus aureus). We describe herein a synthetic route for accessing the corresponding R-syn diastereomer using a key diastereoselective reduction with Baker's yeast, and report on the scope of this reaction for modified systems. Interestingly, whilst the R-anti diastereomer is the only one to show antibacterial activity, the R-syn isomer proved to be significantly more potent against the malaria parasite (IC50 of 2.4 +/- 0.2 mu M). Our research underlines the striking influence that stereochemistry has on the biological activity of pantothenamides, and may find utility in the study of various CoA-utilizing systems. (C) 2014 Published by Elsevier Ltd.
    DOI:
    10.1016/j.bmcl.2014.06.013
  • 作为产物:
    描述:
    (R)-diethyl 2-allyl-2-methyl-3-oxosuccinate丁烯酮 作用下, 以 为溶剂, 反应 24.0h, 以68%的产率得到(2R,3R)-diethyl 2-allyl-3-hydroxy-2-methylsuccinate
    参考文献:
    名称:
    Stereochemical modification of geminal dialkyl substituents on pantothenamides alters antimicrobial activity
    摘要:
    Pantothenamides are N-substituted pantothenate derivatives which are known to exert antimicrobial activity through interference with coenzyme A (CoA) biosynthesis or downstream CoA-utilizing proteins. A previous report has shown that replacement of the ProR methyl group of the benchmark N-pentylpantothenamide with an allyl group (R-anti configuration) yielded one of the most potent antibacterial pantothenamides reported so far (MIC of 3.2 mu M for both sensitive and resistant Staphylococcus aureus). We describe herein a synthetic route for accessing the corresponding R-syn diastereomer using a key diastereoselective reduction with Baker's yeast, and report on the scope of this reaction for modified systems. Interestingly, whilst the R-anti diastereomer is the only one to show antibacterial activity, the R-syn isomer proved to be significantly more potent against the malaria parasite (IC50 of 2.4 +/- 0.2 mu M). Our research underlines the striking influence that stereochemistry has on the biological activity of pantothenamides, and may find utility in the study of various CoA-utilizing systems. (C) 2014 Published by Elsevier Ltd.
    DOI:
    10.1016/j.bmcl.2014.06.013
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