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2-methyl-2-[(2S)-2-oxiranyl]-1-propanol | 104708-02-3

中文名称
——
中文别名
——
英文名称
2-methyl-2-[(2S)-2-oxiranyl]-1-propanol
英文别名
2-methyl-2-[(2S)-oxiran-2-yl]propan-1-ol
2-methyl-2-[(2S)-2-oxiranyl]-1-propanol化学式
CAS
104708-02-3
化学式
C6H12O2
mdl
——
分子量
116.16
InChiKey
FMSOMPFGGXYNKV-RXMQYKEDSA-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

计算性质

  • 辛醇/水分配系数(LogP):
    0.4
  • 重原子数:
    8
  • 可旋转键数:
    2
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    1.0
  • 拓扑面积:
    32.8
  • 氢给体数:
    1
  • 氢受体数:
    2

反应信息

  • 作为反应物:
    描述:
    参考文献:
    名称:
    Fluoronaphthyridines and -quinolones as antibacterial agents. 5. Synthesis and antimicrobial activity of chiral 1-tert-butyl-6-fluoro-7-substituted-naphthyridones
    摘要:
    A series of novel 7-substituted-1-tert-butyl-6-fluoronaphthyridone-3-carboxylic acids has been prepared. These derivatives are characterized by chiral aminopyrrolidine substituents at the 7 position. In this paper we report the full details of the asymmetric synthesis of this series of compounds. Structure-activity relationship studies indicate that the absolute stereochemistry at the asymmetric centers of the pyrrolidine ring is critical for maintaining good activity. Compounds 60 and 61 (3-amino-4-methylpyrrolidine enantiomers) were selected for preclinical evaluation.
    DOI:
    10.1021/jm00100a028
  • 作为产物:
    描述:
    D-(-)-泛酰内酯4-二甲氨基吡啶 二异丁基氢化铝potassium carbonate 、 sodium sulfate 作用下, 以 吡啶甲醇 为溶剂, 反应 4.0h, 生成 2-methyl-2-[(2S)-2-oxiranyl]-1-propanol
    参考文献:
    名称:
    Convenient access to two enantiomeric oxirane synthons bearing a quaternary gem-dimethyl carbon center: Synthesis of 3S-(+) and 3R-(−)-2,2-dimethyl-3,4-oxo-1-butanol from R-(−)-pantolactone
    摘要:
    DOI:
    10.1016/s0040-4039(00)84071-x
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文献信息

  • Total Synthesis and Biological Evaluation of Irciniastatin A (a.k.a. Psymberin) and Irciniastatin B
    作者:Shun-ichiro Uesugi、Tsubasa Watanabe、Takamichi Imaizumi、Yu Ota、Keisuke Yoshida、Haruna Ebisu、Takumi Chinen、Yoko Nagumo、Masatoshi Shibuya、Naoki Kanoh、Takeo Usui、Yoshiharu Iwabuchi
    DOI:10.1021/acs.joc.5b02256
    日期:2015.12.18
    B are members of the pederin natural product family, which have potent antitumor activity and structural complexity. Herein, we describe a full account of our total synthesis of (+)-irciniastatin A and (−)-irciniastatin B. Our synthesis features the highly regioselective Eu(OTf)3-catalyzed, DTBMP-assisted epoxide ring opening reaction with MeOH, which enabled a concise synthesis of the C1–C6 fragment
    Irciniastatin A(又称Psymberin)和irciniastatin B是pederin天然产品家族的成员,它们具有强大的抗肿瘤活性和结构复杂性。本文中,我们全面描述了(+)-irciniastatin A和(-)-irciniastatin B的总合成。我们的合成具有高区域选择性Eu(OTf)3催化的DTBMP辅助的MeOH环氧化物开环反应,可以简明合成C1-C6片段,并广泛使用AZADO(2-azaadamantane N-氧基)及其相关的硝氧基自由基/氧铵盐催化的醇氧化,贯穿整个合成过程,以及C1-C6,C8-C16和C17-C25片段的后期组装。此外,对于(-)-irciniastatin B的合成,我们通过区域选择性脱保护和AZADO催化的醇氧化实现了对氧化阶段的C11选择性控制。合成的irciniastatins对哺乳动物细胞显示出高水平的细胞毒活性。此外,使用
  • Syntheses and Biological Evaluation of Irciniastatin A and the C1−C2 Alkyne Analogue
    作者:Tsubasa Watanabe、Takamichi Imaizumi、Takumi Chinen、Yoko Nagumo、Masatoshi Shibuya、Takeo Usui、Naoki Kanoh、Yoshiharu Iwabuchi
    DOI:10.1021/ol1000389
    日期:2010.3.5
    Syntheses of both natural (+)- and unnatural (-)-irciniastatin A (aka psymberin) as well as a C1-C2 alkyne analogue of (+)-irciniastatin A have been achieved. The key features of the syntheses include a highly regioselective epoxide-opening reaction and a late-stage assembly of C1-C6, C8-C16, and C17-C25 fragments. (+)-Alkymberin retained a high level of cytotoxicity, whereas (-)-irciniastatin A showed almost no activity. These results suggest that (+)-alkymberin could be a useful enantio-differential probe for mode-of-action study.
  • A Modular Enantioselective Approach to Construction of the Macrolactone Core of Polycavernoside A
    作者:Leo A. Paquette、Dmitri Pissarnitski、Louis Barriault
    DOI:10.1021/jo981083t
    日期:1998.10.1
    A program directed toward a total synthesis of polycavernoside A is described. The synthesis of five building blocks is detailed. The first of two electrophilic units, the lactone 3, was prepared in four steps from the known enantiomerically pure oxirane 15. Pyranyl aldehyde 5 was elaborated in turn from L-malic acid via 10. While the route to 30 involved 3 as a starting material, dithiane 2 was obtained in a straightforward manner from 10 as well. The merging of the chiral sectors could not be accomplished by way of the lithiated dithianyl anions, presumably as a consequence of their heightened basicity. The strategic incorporation of the trienyl sector was accomplished, although no attempt was made to control the diastereoselectivity of the process.
  • Convenient access to two enantiomeric oxirane synthons bearing a quaternary gem-dimethyl carbon center: Synthesis of 3S-(+) and 3R-(−)-2,2-dimethyl-3,4-oxo-1-butanol from R-(−)-pantolactone
    作者:Pierre Lavallée、Réjean Ruel、Louis Grenier、Martine Bissonnette
    DOI:10.1016/s0040-4039(00)84071-x
    日期:1986.1
  • Fluoronaphthyridines and -quinolones as antibacterial agents. 5. Synthesis and antimicrobial activity of chiral 1-tert-butyl-6-fluoro-7-substituted-naphthyridones
    作者:P. Di Cesare、D. Bouzard、M. Essiz、J. P. Jacquet、B. Ledoussal、J. R. Kiechel、P. Remuzon、R. E. Kessler、J. Fung-Tomc、J. Desiderio
    DOI:10.1021/jm00100a028
    日期:1992.10
    A series of novel 7-substituted-1-tert-butyl-6-fluoronaphthyridone-3-carboxylic acids has been prepared. These derivatives are characterized by chiral aminopyrrolidine substituents at the 7 position. In this paper we report the full details of the asymmetric synthesis of this series of compounds. Structure-activity relationship studies indicate that the absolute stereochemistry at the asymmetric centers of the pyrrolidine ring is critical for maintaining good activity. Compounds 60 and 61 (3-amino-4-methylpyrrolidine enantiomers) were selected for preclinical evaluation.
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