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3-azido-1-(4-methoxy-phenyl)-propan-1-one | 640734-60-7

中文名称
——
中文别名
——
英文名称
3-azido-1-(4-methoxy-phenyl)-propan-1-one
英文别名
3-Azido-1-(4-methoxyphenyl)propan-1-one
3-azido-1-(4-methoxy-phenyl)-propan-1-one化学式
CAS
640734-60-7
化学式
C10H11N3O2
mdl
——
分子量
205.216
InChiKey
LKLDEFZLGYVYNZ-UHFFFAOYSA-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):
    2.8
  • 重原子数:
    15
  • 可旋转键数:
    5
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.3
  • 拓扑面积:
    40.7
  • 氢给体数:
    0
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    3-azido-1-(4-methoxy-phenyl)-propan-1-one 在 sodium tetrahydroborate 作用下, 以 甲醇 为溶剂, 反应 2.0h, 生成 (RS)-3-azido-1-(4-methoxyphenyl)propan-1-ol
    参考文献:
    名称:
    Synthesis of enantiomerically pure γ-azidoalcohols by lipase-catalyzed transesterification
    摘要:
    An enantioselective synthesis of chiral gamma-azidoalcohols via lipase-catalyzed resolution is described. The efficiency of various lipases and the effect of different solvents have been studied. Pseudomonas cepacia immobilized on diatomaceous earth (PS-D) in n-hexane catalyzed the transesterification process in an efficient manner providing gamma-azidoalcohols in high enantiomeric excess. (C) 2008 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.tetasy.2008.03.028
  • 作为产物:
    描述:
    3-bromo-1-(4-methoxyphenyl)propan-1-one 在 sodium azide 作用下, 以 N,N-二甲基甲酰胺 为溶剂, 反应 2.0h, 生成 3-azido-1-(4-methoxy-phenyl)-propan-1-one
    参考文献:
    名称:
    Azido carbonyl compounds as DNA cleaving agents
    摘要:
    Irradiation of azido carbonyl compounds using UV light (>= 310 nm) produced triplet alkyl nitrenes and aroyl radicals, which resulted in efficient cleavage of single strand DNA at pH 7.0. DNA cleaving ability of azido carbonyl compounds was found to be dependent on its concentration and substituents on its aromatic ring. Further, newly synthesized naphthalene based azido carbonyl compounds showed DNA cleavage ability at longer wavelength of UV light (>= 350 nm) and also binding studies revealed that they bind to ct-DNA by weak intercalation mode. (C) 2012 Elsevier B.V. All rights reserved.
    DOI:
    10.1016/j.jphotobiol.2012.06.006
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文献信息

  • Regiocontrolled Wacker Oxidation of Cinnamyl Azides
    作者:Angela S. Carlson、Cristian Calcanas、Ryan M. Brunner、Joseph J. Topczewski
    DOI:10.1021/acs.orglett.8b00344
    日期:2018.3.16
    A highly regioselective Wacker oxidation has been developed for the oxidation of cinnamyl azides. The catalytic oxidation tolerates the azide functionality, and more than 15 β-azido ketones were isolated (25–92% yield). High regioselectivity for the aryl ketone is observed in all cases. A robustness screen was conducted to determine functional group tolerance. The products of the oxidaiton can be readily
    已经开发出对肉桂酰叠氮化物进行氧化的高度区域选择性的瓦克氧化。催化氧化可耐受叠氮化物的功能,并分离出15种以上的β-叠氮基酮(收率25-92%)。在所有情况下均观察到对芳基酮的高区域选择性。进行了健壮性筛选以确定官能团耐受性。氧化产物可以容易地多样化。
  • Selective Formation of Triplet Alkyl Nitrenes from Photolysis of β-Azido-Propiophenone and Their Reactivity
    作者:Pradeep N. D. Singh、Sarah M. Mandel、Jagadis Sankaranarayanan、Sivaramakrishnan Muthukrishnan、Mingxin Chang、Rachel M. Robinson、Paul M. Lahti、Bruce S. Ault、Anna D. Gudmundsdóttir
    DOI:10.1021/ja077523s
    日期:2007.12.1
    formation of triplet alkyl nitrenes 2 that were detected directly with laser flash photolysis (lambdamax = 325 nm, tau = 27 ms) and ESR spectroscopy (|D/hc| = 1.64 cm-1, |E/hc| = 0.004 cm-1). Nitrenes 2 were further characterized with argon matrix isolation, isotope labeling, and molecular modeling. The triplet alkyl nitrenes are persistent intermediates that do not abstract H-atoms from the solvent but
    具有内置敏化剂单元的 β-叠氮苯丙酮生物 1 的光解导致选择性形成三线态烷基氮烯 2,可通过激光闪光光解(λmax = 325 nm,tau = 27 ms)和 ESR 光谱法 (| D/hc| = 1.64 cm-1,|E/hc| = 0.004 cm-1)。氮烯 2 进一步表征为气基质分离、同位素标记和分子建模。三线态烷基氮烯是持久性中间体,不会从溶剂中提取 H 原子,而是通过与另一个三线态氮烯二聚形成偶氮产物而不是与叠氮化物前体反应而发生衰变。偶氮二聚体互变异构并重排形成杂环化合物 3。 具有 n,pi* 构型的氮烯 2a 作为其酮敏化剂部分的最低三重激发态,经历分子内 1,4-H 原子抽象形成双基 6,通过气基质分离、同位素标记和分子建模鉴定。β-叠氮基-对甲氧基苯丙酮,其三线态敏化剂部分的 pi,pi* 最低激发态不经历任何二次光反应,但选择性地仅产生三线态烷基氮烯中间体,二聚形成
  • An Efficient and General Approach to β-Functionalized Ketones
    作者:Jingliang Jiao、Larry X. Nguyen、Dennis R. Patterson、Robert A. Flowers
    DOI:10.1021/ol070159h
    日期:2007.3.1
    cyclopropyl alcohols provides a novel approach to beta-functionalized ketones. The protocol has a number of advantages including short reaction times, ease of reagent handling, and mild, neutral reaction conditions. Overall, this method provides an alternative pathway to important starting materials and intermediates in organic synthesis.
    [结构:见文字]。在取代的环丙基醇的存在下,硝酸铈铵(CAN)对选定的阴离子(N3-,SCN-,I-和Br-)的氧化为β-官能化的酮提供了一种新颖的方法。该方案具有许多优势,包括反应时间短,试剂处理简便以及温和,中性的反应条件。总体而言,该方法为有机合成中重要的起始原料和中间体提供了另一种途径。
  • Organocatalytic β-Azidation of Enones Initiated by an Electron-Donor–Acceptor Complex
    作者:Rajendra P. Shirke、S. S. V. Ramasastry
    DOI:10.1021/acs.orglett.7b02861
    日期:2017.10.6
    β-unsaturated ketones is described. Reaction of the Zhdankin azidoiodane with enones in the presence of a catalytic amount of an amine provides β-azido ketones via the formation of an electron-donor–acceptor complex. The application of this protocol is demonstrated through one-step elaborations leading to the synthesis of unprecedented classes of 1,2,3-triazoles.
    描述了一种操作简单的α,β-不饱和酮的有机催化β-叠氮化。Zhdankin叠氮烷与烯酮在催化量的胺存在下的反应通过电子给体-受体配合物的形成提供了β-叠氮基酮。该协议的应用通过一步一步精炼来证明,该合成导致合成前所未有的1,2,3-三唑类。
  • A simple and fast procedure for efficient synthesis of β- and γ-azidoarylketones
    作者:Pradeep N.D. Singh、Sivaramakrishnan Muthukrishnan、Rajesh S. Murthy、Rodney F. Klima、Sarah M. Mandel、Michael Hawk、Nina Yarbrough、Anna D. Gudmundsdóttir
    DOI:10.1016/j.tetlet.2003.10.033
    日期:2003.12
    A simple and efficient method for preparing beta- and gamma-azido substituted arylketones has been achieved by short microwave irradiation of the corresponding halo arylketones and sodium azide in DMSO. (C) 2003 Elsevier Ltd. All rights reserved.
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