5,6-dimethoxy-2-phenyl-2H-indazole | 57695-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5,6-dimethoxy-2-phenyl-2H-indazole
• 英文别名: 5,6-Dimethoxy-2-phenyl-2H-indazol；2-phenyl-5,6-dimethoxyindazole；5,6-Dimethoxy-2-phenylindazole
• CAS: 57695-87-1
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: YCQIXHXUNIIMEA-UHFFFAOYSA-N

物化性质

• 熔点：
  147-148 °C
• 沸点：
  282.2±33.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Diphenylphosphine oxide 、 5,6-dimethoxy-2-phenyl-2H-indazole 在 rose bengal 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 、 乙腈 为溶剂， 反应 16.0h， 以70%的产率得到(5,6-dimethoxy-2-phenyl-2H-indazol-3-yl)diphenylphosphine oxide
  参考文献：
  名称：

  Visible-Light-Induced Organophotoredox-Catalyzed Phosphonylation of 2H-Indazoles with Diphenylphosphine Oxide

  摘要：

  A metal-free visible-light-induced phosphonylation of 2H-indazoles with diphenylphosphine oxide has been developed using rose bengal as an organophotoredox catalyst under ambient air at room temperature. A library of diphenyl(2-phenyl-2H-indazol-3-yl)phosphine oxide with broad functionalities has been synthesized in high yields. The experimental result suggests the radical pathway of the reaction.

  DOI：

  10.1021/acs.joc.8b02019
• 作为产物：
  描述：

  N-苯基甘氨酸 在 四丁基氟化铵 、 乙酸酐 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 17.33h， 生成 5,6-dimethoxy-2-phenyl-2H-indazole
  参考文献：
  名称：

  Synthesis of 2H-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes

  摘要：

  A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields this protocol, and subsequent Pd-catalyzed coupling reactions can be applied to the halogenated products to generate a structurally diverse library of indazoles.

  DOI：

  10.1021/jo201605v

文献信息

• 2-Substituted-5,6-dimethoxyindazoles
  申请人：Morton-Norwich Products, Inc.

  公开号：US03966760A1

  公开（公告）日：1976-06-29

  Novel 2-substituted-5,6-dimethoxyindazoles of the formula: ##SPC1## Where R is cyclohexyl, phenethyl, phenyl, dimethylamino, aminoalkyl, methoxyethyl, indazolylethyl, tetrahydropyranylmethyl, p-dimethylaminophenyl, 2-hydroxyethyl, allyl, thiazolyl, pyridyl, 2,3-dihydroxypropyl, and hydroxy are useful as central nervous system depressants or hypotensive agents.

  新型2-取代-5,6-二甲氧基吲唑的化学式如下：##SPC1## 其中R为环己基、苯乙基、苯基、二甲胺基、氨基烷基、甲氧基乙基、吲唑基乙基、四氢吡喃基甲基、对-二甲胺基苯基、2-羟乙基、烯丙基、噻唑基、吡啶基、2,3-二羟基丙基和羟基，可用作中枢神经系统抑制剂或降压剂。
• Stereospecific Assembly of Fused Imidazolidines via Tandem Ring Opening/Oxidative Amination of Aziridines with Cyclic Secondary Amines Using Photoredox Catalysis
  作者：Murugan Vijay、Sundaravel Vivek Kumar、Vanaparthi Satheesh、Periyasamy Ananthappan、Hemant Kumar Srivastava、Sundaram Ellairaja、Vairathevar Sivasamy Vasantha、Tharmalingam Punniyamurthy

  DOI：10.1021/acs.orglett.9b02957

  日期：2019.9.20

  Sustainable assembly of imidazolidines is accomplished via a sequential stereospecific ring opening and C–H amination using aziridines with secondary cyclic amines under visible light mediated indazoloquinoline photoredox catalysis at ambient conditions. Optically active aziridines are coupled with high enantiomeric purities. The computational studies provide insights on the redox properties of the

  咪唑烷的可持续组装是通过在环境条件下在可见光介导的吲唑并喹啉光氧化还原催化下，通过氮丙啶与仲环胺的连续立体有序开环和C–H胺化来实现的。旋光氮丙啶与高对映体纯度结合。计算研究提供了关于催化剂的氧化还原性质以及反应概况的见解。
• Potassium Persulfate-Mediated Thiocyanation of 2<i>H</i> -Indazole under Iron-Catalysis
  作者：Amrita Dey、Alakananda Hajra

  DOI：10.1002/adsc.201801232

  日期：2019.2.19

  Potassium persulfate‐mediated thiocyanation of 2H‐indazoles has been developed using ammonium thiocyanate as thiocyanating agent under iron‐catalysis at room temperature. 2‐Aryl‐3‐thiocyanato‐2H‐indazoles are synthesized in good yields with a broad substrates scope. This methodology is also applicable for the selenocyanation of 2H‐indazoles. The mechanistic study suggests the reaction probably proceeds

  在室温下铁催化下，使用硫氰酸铵作为硫氰酸化剂，开发了过硫酸钾介导的2 H-吲唑的硫氰化反应。2-芳基-3-硫氰基-2- H-吲唑的合成产率高，底物范围广。该方法也适用于2 H-吲唑的硒氰化。机理研究表明该反应可能通过自由基途径进行。
• Electrochemically Enabled Dehydrogenative Phosphorothiolation of 2 <i>H</i> ‐Indazoles under Electrolyte‐Free Conditions
  作者：Payel Ghosh、Alakananda Hajra

  DOI：10.1002/adsc.202200932

  日期：2022.12.8

  We have developed an electrochemical method for phosphorothiolation of 2H-indazoles using S-hydrogen phosphorothioates via cross dehydrogenative coupling reaction under metal-free and electrolyte-free conditions. This protocol is compatible with electron donating groups like −Me, −OMe, halogen and elctron withdrawing groups such as −COOEt, affording respective indazolyl phosphorothioates in 62%-91%

  我们开发了一种电化学方法，在无金属和无电解质条件下，通过交叉脱氢偶联反应，使用S -氢硫代磷酸酯对 2 H -吲唑进行硫代磷酸化。该协议与电子捐赠基团如-Me、-OMe、卤素和电子撤回基团如-COOEt 兼容，以 62%-91% 的收率提供相应的吲唑基硫代磷酸酯。综合机理研究表明，反应通过自由基途径进行。
• Aerobic Cu(I)‐Catalyzed Site‐Selective 1,3‐Difunctionalization of Indazole through Cascade C−N and C−O Bond Formation
  作者：Krishna Kanta Das、Asim Kumar Ghosh、Tamanna Mallick、Naznin Ara Begum、Alakananda Hajra

  DOI：10.1002/adsc.202201162

  日期：2023.2.7

  A Cu(I)-catalyzed 1,3 oxo alkylation of indazole has been developed for constructing N-1-alkylated indazolone derivatives. This cascade reaction involves the formation of C−N and C−O bonds through the sequential functionalization of N1 and C3 positions of indazole in 41–89% yields. The photo-physical studies of the synthesized compounds showed efficient quantum yields with high Stoke shift values.

  已开发了 Cu(I) 催化的吲唑 1,3 氧代烷基化反应，用于构建N -1-烷基化吲唑酮衍生物。这种级联反应涉及通过吲唑的 N1 和 C3 位置的顺序功能化形成 C-N 和 C-O 键，产率为 41-89%。合成化合物的光物理研究表明具有高斯托克位移值的有效量子产率。初步实验结果表明本协议通过单电子转移的有氧流形。