2-azidomethyl-2,3-dihydro-1,4-benzodioxine | 128318-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2-azidomethyl-2,3-dihydro-1,4-benzodioxine
• 英文别名: 2-azidomethyl-2,3-dihydro-benzo[1,4]dioxine；2-Azidomethyl-1,4-benzodioxan；2-(Azidomethyl)-2,3-dihydro-1,4-benzodioxine；3-(azidomethyl)-2,3-dihydro-1,4-benzodioxine
• CAS: 128318-80-9
• 化学式: C₉H₉N₃O₂
• mdl: MFCD14652590
• 分子量: 191.189
• InChiKey: AOQZJEWCWSLOCI-UHFFFAOYSA-N

物化性质

• 沸点：
  106 °C(Press: 0.7 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-azidomethyl-2,3-dihydro-1,4-benzodioxine 在 palladium on activated charcoal 氢气 、 四氯化锡 、 三乙胺 作用下， 生成 胍生
  参考文献：
  名称：

  N-Hydroxyl derivatives of guanidine based drugs as enzymatic NO donors

  摘要：

  Recent research suggests that NO may play a role in the physiological effects of some guanidine-containing drugs. In this guanethidine together with their N-hydroxyl derivatives were report, three guanidine-containing drugs (guanadrel, guanoxan, and guanethidine) together with their N-hydroxyl derivatives were synthesized and their NO-releasing abilities catalyzed by nitric oxide synthases (NOSs) and horseradish peroxidase were evaluated. The guanidine containing compounds could not release NO in the presence of NOS or peroxidase. The corresponding N-hydroxyl compounds exhibited Weak NO-releasing ability under the catalyzed of NOS and good NO-releasing ability tinder the oxidation by horseradish peroxidase in the presence of H2O2. These compounds also displayed vasodilatory activity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00456-5
• 作为产物：
  描述：

  2-羟基甲基-1,4-苯二恶 在 Zn(N₃)₂*Py₂ 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以87%的产率得到2-azidomethyl-2,3-dihydro-1,4-benzodioxine
  参考文献：
  名称：

  Zinc Azide Mediated Mitsunobu Substitution. An Expedient Method for the One-Pot Azidation of Alcohols

  摘要：

  在偶氮二羧酸二异丙酯/三苯基膦的存在下，醇与叠氮化锌/双吡啶配合物反应，通过米苏诺布型取代生成各种叠氮化合物。

  DOI：

  10.1055/s-1990-26809

文献信息

• Fused Bicyclic Caspase-1 Inhibitors Assembled by Copper-Free Strain-Promoted Alkyne-Azide Cycloaddition (SPAAC)
  作者：Linghui Qian、Chong-Jing Zhang、Ji'en Wu、Shao Q. Yao

  DOI：10.1002/chem.201603150

  日期：2017.1.5

  Challenges exist in the development of potent and selective small‐molecule inhibitors against caspase‐1. Herein, by making use of the copper‐free strain‐promoted alkyne–azide cycloaddition (SPAAC) reaction between difluorinated cyclooctynes (DIFOs) and various azide‐containing compounds, we showed for the first time that potential caspase‐1 inhibitors could be rapidly synthesized. The resulting fused

  开发针对caspase-1的有效和选择性小分子抑制剂时面临着挑战。在此，通过利用二氟环辛炔（DIFO）与各种含叠氮化合物之间的无铜应变促进炔-叠氮环加成（SPAAC）反应，我们首次证明了可以快速合成潜在的胱天蛋白酶-1抑制剂。生成的稠合双环化合物在结构上类似于Pralnacasan（一种著名的小分子caspase-1抑制剂）的中心部分（P 2 –P 3），在P 4处具有多样性。可以从叠氮化物组件方便地安装的亲本抑制剂的位置。由于我们的SPAAC组装的抑制剂库是使用无铜生物正交化学方法合成的，因此所得的52个成员的库（2个DIFOs×26个叠氮化物）可立即用于随后的基于细胞的筛选，以快速鉴定潜在的可渗透细胞的能力有效抑制内源性caspase-1活性的方法。C1FS是一种最近报道的荧光双光子探针，具有提高的活细胞对内源性caspase-1的成像敏感性，已在体外和LPS / ATP诱导的巨噬细胞
• Synthesis of Novel Estrogen Receptor Antagonists Using Metal-Catalyzed Coupling Reactions and Characterization of Their Biological Activity
  作者：Xiang-Rong Jiang、Pan Wang、Carolyn L. Smith、Bao Ting Zhu

  DOI：10.1021/jm3013773

  日期：2013.4.11

  Estrogen receptor (ER) antagonists are valuable in the treatment of ER-positive human breast cancer. In this study, we designed and synthesized nine new derivatives of 17 beta-estradiol (E-2) with a bulky side chain attached to its C-7 alpha position, and determined their ER antagonistic activity using in vitro bioassays. Four of the derivatives showed a strong inhibition of ER alpha transactivation activity in a luciferase reporter assay and blocked ER alpha interactions with coactivators. Similarly, these derivatives also strongly inhibited the growth of the ER alpha-positive human breast cancer cells. Computational docking analysis was conducted to model the interaction of these antagonists with the human ER alpha and showed that they could tightly bind to the ER alpha in a manner similar to that of ICI-182,780, a pure ER antagonist. These results provide an example that attachment of a bulky side chain to the C-7 alpha position of E-2 can produce ER antagonists with ER affinity comparable to that of ICI-182, 780.
• Rapid Synthesis, Screening, and Identification of Xanthone- and Xanthene-Based Fluorophores Using Click Chemistry
  作者：Junqi Li、Mingyu Hu、Shao Q. Yao

  DOI：10.1021/ol9010344

  日期：2009.7.16

  A panel of new fluorophores with emission wavelengths from blue to yellow regions using the Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction of alkyne-functionalized xanthones and xanthenes with various azides have been synthesized. Screening of the "click" products led to the identification of "hit" fluorophores which showed a fluorescence increase upon triazole formation. These novel "click" fluorophores could potentially be used for bioconjugation and bioimaging purposes.
• US7488751B2
  申请人：——

  公开号：US7488751B2

  公开（公告）日：2009-02-10
• Zinc Azide Mediated Mitsunobu Substitution. An Expedient Method for the One-Pot Azidation of Alcohols
  作者：Marie Claude Viaud、Patrick Rollin

  DOI：10.1055/s-1990-26809

  日期：——

  In the presence of the diisopropyl azodicarboxylate/triphenylphosphine couple, alcohols react with zinc azide/bis-pyridine complex to give various azides via a Mitsunobu-type substitution.

  在偶氮二羧酸二异丙酯/三苯基膦的存在下，醇与叠氮化锌/双吡啶配合物反应，通过米苏诺布型取代生成各种叠氮化合物。