5-(4-fluorophenyl)-4-iodo-1-phenyl-1H-pyrazole-3-carbaldehyde | 1374634-27-1

• 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-(4-fluorophenyl)-4-iodo-1-phenyl-1H-pyrazole-3-carbaldehyde
• CAS: 1374634-27-1
• 化学式: C₁₆H₁₀FIN₂O
• 分子量: 392.171
• InChiKey: FVIZBFGIBQVQHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.89
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(4-fluorophenyl)-4-iodo-1-phenyl-1H-pyrazole-3-carbaldehyde 、 盐酸乙脒 在 copper(l) iodide 、 caesium carbonate 、 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以74%的产率得到3-(4-fluorophenyl)-5-methyl-2-phenyl-2H-pyrazolo[4,3-d]pyrimidine
  参考文献：
  名称：

  铜催化4-碘吡唑衍生物与脒的级联反应合成吡唑并[4,3-d]嘧啶衍生物

  摘要：

  4-碘吡唑甲醛和4-碘吡唑甲酰胺与取代脒的高效铜催化级联反应，用于制备取代吡唑并[4,3-d]嘧啶和吡唑并[4,3-d]嘧啶-7(6H)-酮，分别进行说明。

  DOI：

  10.1002/ejoc.201101454

文献信息

• Substituent-Guided Switch between CH Activation and Decarboxylative Cross-Coupling during Palladium/Copper-Catalyzed Cascade Reactions of 2-Aminobenzoates with 2-Haloarylaldehydes
  作者：Subhendu Bhowmik、Garima Pandey、Sanjay Batra

  DOI：10.1002/chem.201301705

  日期：2013.8.5

  Phenanthridines, pyrazole[4,3‐c]quinolines and isocryptolepine were prepared in one step from the Pd/Cu‐catalyzed reaction between potassium 2‐aminobenzoates and 2‐haloarylaldehydes (see scheme). Although the reactions of 2‐aminobenzoates proceeded via a cascade imination/CH functionalization, the reactions of 6‐nitro‐2‐aminobenzoates ensued via a tandem imination/decarboxylative cross‐coupling.

  级联转换：由2-氨基苯甲酸钾和2-卤代芳基醛之间的Pd / Cu催化反应一步制得菲啶，吡唑[4,3- c ]喹啉和异隐油菜碱（参见方案）。虽然经由级联亚胺化/ C进行2-氨基苯甲酸酯反应 ħ官能化，6-硝基-2-氨基苯甲酸酯的反应中通过串联亚胺化/脱羧交叉偶联接踵而至。
• An efficient metal-free and catalyst-free C–S/C–O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides
  作者：Shubham Sharma、Dharmender Singh、Sunit Kumar、Vaishali、Rahul Jamra、Naveen Banyal、Deepika、Chandi C Malakar、Virender Singh

  DOI：10.3762/bjoc.19.22

  日期：——

  described for the synthesis of pyrazole-tethered thioamide and amide conjugates. The thioamides were generated by employing a three-component reaction of diverse pyrazole C-3/4/5 carbaldehydes, secondary amines, and elemental sulfur in a single synthetic operation. The advantages of this developed protocol refer to the broad substrate scope, metal-free and easy to perform reaction conditions. Moreover

  描述了一种操作简单且无金属的方法，用于合成吡唑系硫代酰胺和酰胺缀合物。硫代酰胺是通过在单一合成操作中采用多种吡唑 C-3/4/5 甲醛、仲胺和元素硫的三组分反应生成的。该开发协议的优点是底物范围广、无金属且易于执行反应条件。此外，还使用过氧化氢作为氧化剂，通过吡唑甲醛和 2-氨基吡啶的氧化胺化合成了吡唑 C-3/5 连接的酰胺缀合物。
• A simple and efficient route to pyrazole-based dihydrofuranones via lactonization approach
  作者：Shubham Sharma、Virender Singh、Vinod Kumar Vashistha、Manpreet Singh、Ashutosh Sharma

  DOI：10.1007/s11696-023-03257-6

  日期：2024.2

  Abstract The diastereoselective synthesis of novel pyrazole and dihydrofuranone-based molecular hybrids has been unfolded through the development of a straightforward tandem strategy. The indium-mediated Barbier-type allylation reaction was followed by an in situ lactonization approach. No additives were required for this transformation, and high yields of dihydrofuranone derivatives were obtained

  摘要 通过开发简单的串联策略，新型吡唑和二氢呋喃酮分子杂化物的非对映选择性合成已经展开。铟介导的巴比尔型烯丙基化反应之后是原位内酯化方法。该转化不需要任何添加剂，并且通过顺式立体化学获得了高产率的二氢呋喃酮衍生物。目前的方案具有许多优点，包括一锅法、高非对映选择性、广泛的底物范围和所需产物的高产率。
• Straightforward copper-catalyzed synthesis of pyrrolopyrazoles from halogenated pyrazolecarbaldehydes
  作者：Maloy Nayak、Harikrishna Batchu、Sanjay Batra

  DOI：10.1016/j.tetlet.2012.05.148

  日期：2012.8

  Straightforward synthesis of a variety of pyrrolo-fused pyrazoles via a cascade reaction between halopyrazolecarbaldehydes and ethylisocyanoacetate in the presence of copper and a base is described. (C) 2012 Elsevier Ltd. All rights reserved.