3-methyl-5-(3-methylbut-2-enylsulfanyl)-1-phenyl-1H-pyrazole-4-carbaldehyde | 160348-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-5-(3-methylbut-2-enylsulfanyl)-1-phenyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 3-Methyl-5-(3-methylbut-2-enylsulfanyl)-1-phenylpyrazole-4-carbaldehyde
• CAS: 160348-48-1
• 化学式: C₁₆H₁₈N₂OS
• 分子量: 286.398
• InChiKey: IHQYLKDWHVFPHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-5-(3-methylbut-2-enylsulfanyl)-1-phenyl-1H-pyrazole-4-carbaldehyde 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 以74%的产率得到(NE)-N-[[3-methyl-5-(3-methylbut-2-enylsulfanyl)-1-phenylpyrazol-4-yl]methylidene]hydroxylamine
  参考文献：
  名称：

  L'abbe, Gerrit; Emmers, Sabine; Dehaen, Wim, Journal of the Chemical Society. Perkin transactions I, 1994, # 18, p. 2553 - 2558

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氯-3-甲基-1-苯基吡唑-4-甲醛 、 1-溴-3-甲基-2-丁烯 在 硫脲 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以73%的产率得到3-methyl-5-(3-methylbut-2-enylsulfanyl)-1-phenyl-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  Diastereoselective intramolecular hetero Diels–Alder approach towards polycyclic heterocycles

  摘要：

  Several different heterocyclic aldehydes, derived from pyrazole. pyrimidine, pyridine, indole and thiazole, were converted to polyheterocyclic compounds containing four to seven rings. The key steps in the sequence were a Knoevenagel condensation of the aldehyde and a heterocyclic carbonyl compound, such as pyrazolone and isoxazolone, followed by an intramolecular hetero Diets-Alder reaction. Most final products were isolated with high yield and diastereoselecivity. The isoxazolo fused cycloadducts formed interesting spiro-adducts upon heating. The cis nature of the bridging hydrogens of the heterocycles was evidenced by X-ray diffraction analysis.(dagger) (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01153-x

文献信息

• BiCl₃-Catalyzed Diastereoselective Intramolecular [4+2] Cycloaddition Reactions Leading to Pyrazole Annulated New Sulfur Heterocycles
  作者：Gowravaram Sabitha、Ch. Srinivas Reddy、Ch. Maruthi、E. Venkata Reddy、J. S. Yadav

  DOI：10.1081/scc-120022482

  日期：2003.9.1

  Abstract Intramolecular [4+2] cycloaddition reactions of N-aryl imines generated in situ from anilines and the S-allyl derivatives of pyrazole aldehydes have been carried out in the presence of catalytic amounts of BiCl3 to provide the corresponding hexahydropyrazolo [4′,3′:5,6]thiopyrano[4,3-b]quinolines in excellent yields. The reactions are highly diastereoselective and the only cis products are

  摘要 苯胺原位生成的 N-芳基亚胺与吡唑醛的 S-烯丙基衍生物在催化量的 BiCl3 存在下进行分子内 [4+2] 环加成反应，得到相应的六氢吡唑并 [4',3] ':5,6]噻喃并[4,3-b]喹啉产率极好。该反应是高度非对映选择性的，唯一的顺式产物是专门分离的。#IICT 通讯编号：020602
• A Highly Diastereoselective Intramolecular <i>Hetero</i> Diels-Alder Approach Towards Tetracyclic Pyrazoles
  作者：Erik Ceulemans、Marieke Voets、Sabine Emmers、Wim Dehaen

  DOI：10.1055/s-1997-978

  日期：1997.10

  A pyrazole aldehyde was used as a starting material for an intramolecular hetero Diels-Alder reaction, affording tetracyclic pyrazoles with high yield and diastereoselectivity. The isoxazolo fused cycloadduct formed interesting spiro-adducts upon heating.

  以吡唑醛为起始原料，进行了分子内杂环 Diels-Alder 反应，以高产率和非对映选择性得到了四环吡唑。异噁唑融合环加合物在加热后会形成有趣的螺加合物。
• Rapid synthesis of tetrahydroquinolines by indium trichloride catalyzed mono- and bis-intramolecular imino Diels–Alder reactions
  作者：Rathna Durga R.S. Manian、Jayadevan Jayashankaran、Rasappan Ramesh、Raghavachary Raghunathan

  DOI：10.1016/j.tetlet.2006.08.088

  日期：2006.10

  A rapid synthesis of mono- and bis-tetrahydropyrazolo[4′,3′:5,6]thiopyrano[4,3-b]quinolines has been achieved by the reaction of aldimines derived from aromatic amines and S-prenylated aldehydes in acetonitrile with InCl3 as a catalyst, in excellent yields and short reaction times, under mild conditions.

  通过衍生自芳族胺的醛亚胺和S-异戊醛化的乙醛在乙腈中与乙醛反应，可以快速合成单-和双-四氢吡唑并[4'，3'：5,6]硫代吡喃并[4,3- b ]喹啉InCl 3作为催化剂，在温和条件下具有极佳的收率和较短的反应时间。
• An efficient synthesis of thiopyrano[5,6-c]coumarin/[6,5-c]chromones through intramolecular domino Knoevenagel hetero Diels–Alder reactions
  作者：Jayadevan Jayashankaran、Rathna Durga R.S. Manian、Raghavachary Raghunathan

  DOI：10.1016/j.tetlet.2006.01.083

  日期：2006.3

  The synthesis of novel polycyclic thiopyrano coumarin/chromone frameworks through intramolecular domino Knoevenagel hetero Diels-Alder reactions of 4-hydroxy coumarin and its benzo-analogous with S-prenylated aromatic aldehydes was studied. A high degree of chemoselectivity was achieved by the application of microwave irradiation and a solid support. (c) 2006 Elsevier Ltd. All rights reserved.
• Diastereoselective intramolecular hetero Diels–Alder approach towards polycyclic heterocycles
  作者：Erik Ceulemans、Marieke Voets、Sabine Emmers、Koen Uytterhoeven、Luc Van Meervelt、Wim Dehaen

  DOI：10.1016/s0040-4020(01)01153-x

  日期：2002.1

  Several different heterocyclic aldehydes, derived from pyrazole. pyrimidine, pyridine, indole and thiazole, were converted to polyheterocyclic compounds containing four to seven rings. The key steps in the sequence were a Knoevenagel condensation of the aldehyde and a heterocyclic carbonyl compound, such as pyrazolone and isoxazolone, followed by an intramolecular hetero Diets-Alder reaction. Most final products were isolated with high yield and diastereoselecivity. The isoxazolo fused cycloadducts formed interesting spiro-adducts upon heating. The cis nature of the bridging hydrogens of the heterocycles was evidenced by X-ray diffraction analysis.(dagger) (C) 2002 Elsevier Science Ltd. All rights reserved.