3-methyl-6-(thiophen-2-yl)pyridazine | 68206-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-methyl-6-(thiophen-2-yl)pyridazine
• 英文别名: 3-Methyl-6-thiophen-2-ylpyridazine
• CAS: 68206-14-4
• 化学式: C₉H₈N₂S
• 分子量: 176.242
• InChiKey: OWZYWYRDRFQPFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 indium(III) triflate 、 hydrazine hydrate 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以72%的产率得到3-methyl-6-(thiophen-2-yl)pyridazine
  参考文献：
  名称：

  In(OTf)3-mediated synthesis of substituted pyridazines

  摘要：

  In(OTf)(3) (4c)-mediated one-pot (4+2) cyclocondensation of gamma-alkynones 3 with N2H4(aq) in dioxane affords substituted pyridazines 5 in good yields via a sequential desulfonative or dehydrogenative aromatization. The facile transformation proceeds by a facile synthetic sequence starting with an alpha-propargylation of beta-ketosulfones 1 and a cyclocondensation of gamma-alkynones 3 with N2H4(aq). The method provides a mild and efficient condition. Moreover, this route can be enlarged to multigram scale. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.025

文献信息

• The Palladium Catalysed Biaryl Cross-Coupling of Pyridazine Triflates
  作者：David J. Aldous、Shelley Bower、Neil Moorcroft、Michael Todd

  DOI：10.1055/s-2001-9716

  日期：——

  The scope of trifluoromethanosulfonic acid 6-methyl-pyridazine-3-yl ester as a coupling partner for biaryl synthesis via palladium catalysed Suzuki and Stille coupling conditions is reported.

  报道了三氟甲基磺酸6-甲基吡啶噻唑-3-基酯作为偶联反应物，在钯催化的铃木和斯蒂尔偶联条件下用于双芳烃合成的范围。
• A New One-Pot Synthesis of 3,6-Disubstituted Pyridazines Starting from β-Nitro-β,γ-Unsaturated Ketones
  作者：Alessandro Palmieri、Muhammad E. I. Khan、Lixia Yuan、Marino Petrini

  DOI：10.1055/a-2114-7673

  日期：2023.10

  A new one-pot preparation of 3,6-disubstituted pyridazines starting from β-nitro-β,γ-unsaturated ketones and hydrazine monohydrate is presented. The protocol entails two sequential steps, leading to the isolation of the title targets in satisfactory overall yields tolerating a good variety of additional functionalities.

  提出了一种以 β-硝基-β,γ-不饱和酮和一水合肼为起始原料的 3,6-二取代哒嗪的新型一锅法制备方法。该协议需要两个连续的步骤，从而以令人满意的总体产量隔离标题目标，并耐受多种附加功能。
• Heteroaryl–Heteroaryl Suzuki–Miyaura Cross-Coupling Enabled by Large-but-Flexible Dibenzobarrelene-Derived Pd-NHC Precatalysts
  作者：Mia Guo、Yu Zhang、Meng-Jiao Zhang、Tian Li、Jia-Yi Wu、Feng-Shou Liu

  DOI：10.1021/acs.organomet.3c00225

  日期：2023.8.14

  in Pd-catalyzed challenging heteroaryl–heteroaryl Suzuki–Miyaura cross-coupling reactions under aerobic conditions, exhibiting a general and highly efficient protocol for a range of challenging substrates. Additionally, the current protocols were successfully applied to the synthesis of valuable functional small molecules and conjugated mesopolymers. These findings have significant implications for the

  本研究描述了一类由二苯并桶烯衍生的“大而灵活”的 Pd-NHC 配合物。这些配合物已成功用于有氧条件下钯催化的具有挑战性的杂芳基-杂芳基铃木-宫浦交叉偶联反应，展示了针对一系列具有挑战性的底物的通用且高效的方案。此外，当前的方案已成功应用于有价值的功能小分子和共轭介观聚合物的合成。这些发现对于有机和功能材料合成领域新型高效催化方法的开发具有重要意义。
• Ohsawa,A. et al., Chemical and pharmaceutical bulletin, 1978, vol. 26, p. 2550 - 2554
  作者：Ohsawa,A. et al.

  DOI：——

  日期：——
• In(OTf)3-mediated synthesis of substituted pyridazines
  作者：Meng-Yang Chang、Yi-Ju Lu、Yu-Chieh Cheng

  DOI：10.1016/j.tet.2015.07.025

  日期：2015.9

  In(OTf)(3) (4c)-mediated one-pot (4+2) cyclocondensation of gamma-alkynones 3 with N2H4(aq) in dioxane affords substituted pyridazines 5 in good yields via a sequential desulfonative or dehydrogenative aromatization. The facile transformation proceeds by a facile synthetic sequence starting with an alpha-propargylation of beta-ketosulfones 1 and a cyclocondensation of gamma-alkynones 3 with N2H4(aq). The method provides a mild and efficient condition. Moreover, this route can be enlarged to multigram scale. (C) 2015 Elsevier Ltd. All rights reserved.