4-trimethylsilyl-3-butyn-2-one phenylhydrazone | 460095-38-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-trimethylsilyl-3-butyn-2-one phenylhydrazone
• 英文别名: N-(4-trimethylsilylbut-3-yn-2-ylideneamino)aniline
• CAS: 460095-38-9
• 化学式: C₁₃H₁₈N₂Si
• 分子量: 230.385
• InChiKey: CRQMBHUUTOFMTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  24.39
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-trimethylsilyl-3-butyn-2-one phenylhydrazone 在 碘 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到4-iodo-3-methyl-5-trimethylsilyl-1-phenylpyrazole
  参考文献：
  名称：

  Regiospecific synthesis of 5-silyl azoles

  摘要：

  5-Silylisoxazoles bearing other silyl groups different to the more usual trimethylsilyl have been prepared by condensation of silylalkynones with hydroxylamine hydrochloride. The reaction with hydrazines is more complex and leads to 5-silylpyrazoles or the corresponding hydrazones, which can be cyclized by reaction with electrophiles. This has allowed us to synthesize 5-silylpyrazoles functionalized at C-4 by groups impossible to introduce by electrophilic substitution of the pyrazole nucleus. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00386-1
• 作为产物：
  描述：

  1-dimethylphenylsilyl-2-trimethylsilylacetylene 在 三氯化铝 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 4-trimethylsilyl-3-butyn-2-one phenylhydrazone
  参考文献：
  名称：

  Regiospecific synthesis of 5-silyl azoles

  摘要：

  5-Silylisoxazoles bearing other silyl groups different to the more usual trimethylsilyl have been prepared by condensation of silylalkynones with hydroxylamine hydrochloride. The reaction with hydrazines is more complex and leads to 5-silylpyrazoles or the corresponding hydrazones, which can be cyclized by reaction with electrophiles. This has allowed us to synthesize 5-silylpyrazoles functionalized at C-4 by groups impossible to introduce by electrophilic substitution of the pyrazole nucleus. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00386-1

文献信息

• A Novel Synthesis of Fluorinated Pyrazoles via Gold(I)-Catalyzed Tandem Aminofluorination of Alkynes in the Presence of Selectfluor
  作者：Jianqiang Qian、Yunkui Liu、Jie Zhu、Bo Jiang、Zhenyuan Xu

  DOI：10.1021/ol201555z

  日期：2011.8.19

  A mild and efficient protocol for the synthesis of fluorinated pyrazoles has been developed via gold(I)-catalyzed tandem aminofluorination of alkynes in the presence of Selectfluor. This method offers a broad substrate scope.

  在Selectfluor的存在下，通过金（I）催化的炔烃的串联氨基氟化，已经开发了一种温和而有效的合成氟化吡唑的方案。该方法提供了广泛的基材范围。
• Cyclization–carbonylation–cyclization coupling reaction of α,β-alkynic hydrazones with palladium(ii)-bisoxazoline catalyst
  作者：Taichi Kusakabe、Hiroshi Sagae、Keisuke Kato

  DOI：10.1039/c3ob40913a

  日期：——

  A cyclization–carbonylation–cyclization coupling reaction (CCC-coupling reaction) of α,β-alkynic hydrazones, catalyzed by (box)PdII complexes, afforded symmetrical ketones bearing two pyrazole groups in good to excellent yields. This method is applicable to a broad range of substrates.

  在(box)PdII络合物的催化下，δ,δ-炔酰肼的环化-羰基化-环化偶联反应（CCC-偶联反应）以良好至极佳的收率获得了带有两个吡唑基团的对称酮。这种方法适用于多种底物。
• Pd(<scp>ii</scp>)-catalyzed ligand controlled synthesis of pyrazole-4-carboxylates and benzo[b]thiophene-3-carboxylates
  作者：Yogesh Daulat Dhage、Hiroki Daimon、Cheng Peng、Taichi Kusakabe、Keisuke Takahashi、Yuichiro Kanno、Yoshio Inouye、Keisuke Kato

  DOI：10.1039/c4ob01576b

  日期：——

  A simple change of the ligand and solvent allows controlled, effective switching between cyclization–carbonylation–cyclization-coupling (CCC-coupling) and cyclization–carbonylation reactions.

  通过简单更改配体和溶剂，可以实现在环化-羰基化-环化偶联（CCC偶联）和环化-羰基化反应之间的可控、有效切换。