1-diazohept-6-yn-2-one | 139885-08-8

• 分子结构分类: 有机化合物 - 乙炔化物 - 碳化物
• 英文名称: 1-diazohept-6-yn-2-one
• 英文别名: 1-Diazoniohept-1-en-6-yn-2-olate
• CAS: 139885-08-8
• 化学式: C₇H₈N₂O
• 分子量: 136.153
• InChiKey: RLBKFEZYCKXVDC-UHFFFAOYSA-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：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  19.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-diazohept-6-yn-2-one 在 氢溴酸 、 三氟乙酸 作用下， 以 溶剂黄146 为溶剂， 生成 4-Pent-4-ynyl-[1,3]dithiole-2-thione
  参考文献：
  名称：

  New long-chain tetrathiafulvalene derivatives with a diacetylene group

  摘要：

  The multi-stage synthesis of new long-chain tetrathiafulvalene derivatives containing a diacetylene group at different distances from tetrathiafulvalene moiety - 2-(tetracosa-9, 11-diynyle)-, 2-heptadeca-9, 11-diynyle)- and 2-(nonadeca-4,6-diynyle)-6,7-tetrathiafulvalene is described.

  DOI：

  10.1016/s0040-4039(00)91591-0
• 作为产物：
  描述：

  5-己炔酸 在 草酰氯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 1-diazohept-6-yn-2-one
  参考文献：
  名称：

  三甲基甲硅烷基重氮甲烷作为多功能缝线剂，用于将氮丙啶引入功能化有机分子中

  摘要：

  通过串联酰化和叠氮化TMSCHN 2开发了将氮丙啶引入功能化有机分子的高度对映选择性的途径。

  DOI：

  10.1021/ol102064b

文献信息

• Tandem alkyne insertion and allyl sulfonium ylide rearrangement of γ,δ-alkynyl-α′-diazoketones
  作者：Thomas R. Hoye、Christopher J. Dinsmore

  DOI：10.1016/0040-4039(92)88041-3

  日期：1992.1

  catalytic rhodium carboxylate dimer and diallylsulfide (1.1 equiv), undergo sequential alkyne insertion/ylide formation/sigmatropic rearrangement to give γ-allylthio cyclic enones. This transformation was used to probe the influence of alkyne substituents on 5-exo vs. 6-endo cyclization selectivity in the alkyne insertion event.

  乙炔α-重氮酮1在用催化羧酸铑二聚体和二烯丙基硫醚（1.1当量）处理时，会依次进行炔烃插入/内酯形成/σ重排，得到γ-烯丙基硫代环烯酮。此转化用于探测炔烃插入事件中炔烃取代基对5-exo与6-endo环化选择性的影响。
• Synthesis and Antitumor Activity of a Novel Series of 6-Substituted Pyrrolo[2,3-<i>d</i>]pyrimidine Thienoyl Antifolate Inhibitors of Purine Biosynthesis with Selectivity for High Affinity Folate Receptors and the Proton-Coupled Folate Transporter over the Reduced Folate Carrier for Cellular Entry
  作者：Lei Wang、Christina Cherian、Sita Kugel Desmoulin、Lisa Polin、Yijun Deng、Jianmei Wu、Zhanjun Hou、Kathryn White、Juiwanna Kushner、Larry H. Matherly、Aleem Gangjee

  DOI：10.1021/jm9015729

  日期：2010.2.11

  ituted pyrrolo[2,3-d]pyrimidines with a thienoyl side chain and four to six carbon bridge lengths (compounds 1−3) were synthesized as substrates for folate receptors (FRs) and the proton-coupled folate transporter (PCFT). Conversion of acetylene carboxylic acids to α-bromomethylketones and condensation with 2,4-diamino-6-hydroxypyrimidine afforded the 6-substituted pyrrolo[2,3-d]pyrimidines. Sonogashira

  合成了具有噻吩酰基侧链和 4 到 6 个碳桥长度的2-氨基-4-氧代-6-取代的吡咯并[2,3- d ]嘧啶（化合物1 - 3）作为叶酸受体 (FR) 的底物和质子偶联叶酸转运蛋白 (PCFT)。乙炔羧酸转化为α-溴甲基酮并与2,4-二氨基-6-羟基嘧啶缩合得到6-取代的吡咯并[2,3- d ]嘧啶。薗头与（耦合小号）-2 - [（5-溴-噻吩-2-羰基） -氨基] -戊二酸二乙酯，随后氢化和皂化，得到1 - 3。化合物1和2有效抑制表达 FRα、减少叶酸载体 (RFC) 和 PCFT 的 KB 和 IGROV1 人类肿瘤细胞。类似物对 FR 和 PCFT 比 RFC 具有选择性。甘氨酰胺核糖核苷酸甲酰转移酶是主要的细胞靶标。在具有 KB 肿瘤的 SCID 小鼠中，1对早期（3.5 log 杀死，1/5 治愈）和晚期（3.7 log 杀死，4/5 完全缓解）阶段的肿瘤具有高度活性。我们的结果表明，由于
• Novel Ag(I)-catalysis of an intramolecular 1,3-dipolar cycloaddition
  作者：Andrew S. Kende、Michel Journet

  DOI：10.1016/0040-4039(95)00470-w

  日期：1995.5

  Acetylenic α-diazoketones, bearing gem-dimethyl substituents in the α′ position, were found to undergo an intramolecular 1,3-dipolar cycloaddition reaction in the presence of silver(I) as catalyst. In that instance, bicyclic pyrazole derivatives were isolated in 47 to 55% yield, even in the conditions of the Arndt-Eistert reaction. The requirement for gem-dimethyl substitution in acyclic substrates is rationalized

  发现在银（I）作为催化剂的存在下，在α'位置带有宝石-二甲基取代基的乙炔α-二氮杂环酮发生分子内的1,3-偶极环加成反应。在这种情况下，即使在Arndt-Eistert反应条件下，也以47％至55％的收率分离出双环吡唑衍生物。根据过渡态对构象能的空间效应，合理化了无环底物中对宝石二甲基取代的要求。
• Modulating the development of E. coli biofilms with 2-aminoimidazoles
  作者：Catherine S. Reed、Robert W. Huigens、Steven A. Rogers、Christian Melander

  DOI：10.1016/j.bmcl.2010.08.075

  日期：2010.11

  The synthesis of a 20 member 2-aminoimidazole/triazole pilot library is reported. Each member of the library was screened for its ability to inhibit or promote biofilm development of either Escherichia coli and Acinetobacter baumannii. From this screen, E. coli-selective 2-aminoimidazoles were discovered, with the best inhibitor inhibiting biofilm development with an IC(50) of 13 mu M. The most potent promoter of E. coli biofilm formation promoted biofilm development by 321% at 400 mu M. (C) 2010 Elsevier Ltd. All rights reserved.
• Oxazole activation for azomethine ylide trapping: singly and doubly tethered substrates
  作者：Edwin Vedejs、David W. Piotrowski

  DOI：10.1021/jo00058a010

  日期：1993.3

  Bicyclic oxazolium salts 18, 24, 37, and 44 can be generated from tethered haloalkyloxazoles by internal alkylation. Reductive alkylation of the oxazolium salts using CsF/PhSiH3 converts the salts initially into the corresponding 4-oxazoline derivatives. Subsequent electrocyclic ring opening generates stabilized azomethine ylides that can be trapped by suitable dipolarophiles. Intermolecular dipole trapping followed by DDQ oxidation affords the ring-fused pyrroles 22 and 26. When tethered alkynoates are used for internal dipole trapping, the adducts 38 and 45 can be obtained by a similar reductive activation sequence, followed by DDQ workup. Effective procedures for the internal oxazole N-alkylation step are described using an acetonitrile-trifluoroethanol solvent system. Also, an improved method for the generation of the dichlorocerium derivative of ethyl propiolate and intermolecular trapping by an aldehyde is reported.