cinnamaldehyde tosylhydrazone | 7318-33-4

• 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: cinnamaldehyde tosylhydrazone
• 英文别名: cinnamaldehyde p-tosylhydrazone；cinnamaldehyde N-tosylhydrazone；4-methyl-N′-3-(phenylallylidene)benzenesulfonohydrazide；Cinnamaldehyde tosyl hydrazone；N-(cinnamylideneamino)-4-methylbenzenesulfonamide
• CAS: 7318-33-4
• 化学式: C₁₆H₁₆N₂O₂S
• 分子量: 300.381
• InChiKey: KTJCQVMWEPIPJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  cinnamaldehyde tosylhydrazone 在 bismuth(III) chloride 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.03h， 以86%的产率得到肉桂醛
  参考文献：
  名称：

  Bi⁺³-Catalyzed Regeneration of Carbonyl Compounds from Hydrazones Under Microwave Irradiation

  摘要：

  开发了一种新颖且高效的方法，利用微波辐射在潮湿的四氢呋喃中，用催化量的氯化铋对二甲基和磺酰肼佐剂1的C=N键进行水解 cleavage，生成相应的羰基化合物2。

  DOI：

  10.1055/s-1997-1014
• 作为产物：
  描述：

  苯甲醛 以 甲醇 、 乙醇 、 水 为溶剂， 反应 0.08h， 生成 cinnamaldehyde tosylhydrazone
  参考文献：
  名称：

  Palladium-Catalyzed Cleavage of α-Allenylic Aryl Ether toward Pyrazolemethylene-Substituted Phosphinyl Allenes and Their Transformations via Alkenyl C–P(O) Cleavage

  摘要：

  A palladium-catalyzed two-component coupling of allenylphosphine oxides with conjugated N-tosylhydrazones is revealed. For the first time, the cleavage of a-allenylic aryl ether toward pyrazolemethylene-substituted phosphinyl allenes enabled facile synthesis of combined motifs with pyrazole and allene. Moreover, the obtained adducts could be easily transformed to potential bioactive multifunctionalized phosphinates via a novel alkenyl C-P(O) cleavage.

  DOI：

  10.1021/acs.orglett.7b00213

文献信息

• Deoxygenation of Aldehydes and Ketones Using Dichloro Bis(1,4-diazabicyclo[2.2.2]octane)(tetrahydroborato) Zirconium(IV)
  作者：Heshmatollah Alinezhad、Mahmood Tajbakhsh、Fatemeh Salehian

  DOI：10.1055/s-2004-836038

  日期：——

  Saturated aldehydes and ketones are converted via their p-toluenesulfonyl hydrazones to the corresponding alkanes using dichloro bis(1,4-diazabicydo[2.2.2]octane)(tetrahydroborato) zirconium(IV) (ZrBDC). The reactions were performed in DMF-sulfolane at 110 °C and gave the corresponding alkanes in high yields. Regioselectivity in the reduction of α,β-unsaturated carbonyl groups was also observed.

  使用二氯双(1,4-二氮杂双环[2.2.2]辛烷)(四氢硼酸)锆(IV) (ZrBDC)，饱和醛和酮通过它们的对甲苯磺酰腙转化为相应的烷烃。该反应在 DMF-环丁砜中于 110°C 下进行，并以高产率得到相应的烷烃。还观察到 α,β-不饱和羰基还原的区域选择性。
• Base-Promoted Coupling of Carbon Dioxide, Amines, and<i>N</i>-Tosylhydrazones: A Novel and Versatile Approach to Carbamates
  作者：Wenfang Xiong、Chaorong Qi、Haitao He、Lu Ouyang、Min Zhang、Huanfeng Jiang

  DOI：10.1002/anie.201410605

  日期：2015.3.2

  A base‐promoted three‐component coupling of carbon dioxide, amines, and N‐tosylhydrazones has been developed. The reaction is suggested to proceed via a carbocation intermediate and constitutes an efficient and versatile approach for the synthesis of a wide range of organic carbamates. The advantages of this method include the use of readily available substrates, excellent functional group tolerance

  已开发出碱促进的二氧化碳，胺和N-甲苯磺酰hydr的三组分偶联剂。建议该反应通过碳正离子中间体进行，并且构成用于合成多种有机氨基甲酸酯的有效且通用的方法。该方法的优点包括使用易于获得的底物，出色的官能团耐受性，广泛的底物范围以及简便的后处理程序。
• Metal-free and highly regioselective synthesis of N-heteroaryl substituted pyrazoles from α,β-unsaturated N-tosylhydrazones and heteroaryl chlorides
  作者：Lin Zeng、Xiao-Qiang Guo、Zai-Jun Yang、Ya Gan、Lian-Mei Chen、Tai-Ran Kang

  DOI：10.1016/j.tetlet.2019.07.034

  日期：2019.8

  β-unsaturated N-tosylhydrazones with N-heteroaryl chlorides was developed for the synthesis of N-heteroaryl pyrazole derivatives. This one-pot reaction provided bi(heteroaryl) derivatives in good to excellent yields and with excellent regioselectivity. The procedure is operationally simple and applicable to large-scale synthesis.

  级联环化/亲核芳香取代（S Ñ AR）α的反应，β不饱和Ñ与-tosylhydrazones ñ -杂芳基氯化物被用于合成开发Ñ -杂芳基吡唑衍生物。该一锅法反应以良好的至优异的产率和优异的区域选择性提供了双（杂芳基）衍生物。该程序操作简单，适用于大规模合成。
• Copper(I)-Catalyzed Alkylation of Polyfluoroarenes through Direct CH Bond Functionalization
  作者：Shuai Xu、Guojiao Wu、Fei Ye、Xi Wang、Huan Li、Xia Zhao、Yan Zhang、Jianbo Wang

  DOI：10.1002/anie.201412450

  日期：2015.4.7

  The copper(I)‐catalyzed alkylation of electron‐deficient polyfluoroarenes with N‐tosylhydrazones and diazo compounds has been developed. This reaction uses readily available starting materials and is operationally simple, thus representing a practical method for the construction of C(sp2)C(sp3) bonds with polyfluoroarenes through direct CH bond functionalization. Mechanistically, copper(I) carbene

  已经开发了N-甲苯磺酰hydr和重氮化合物对缺电子的多氟芳烃进行铜（I）催化的烷基化反应。该反应使用容易获得的起始原料并且操作简单，因此代表了通过直接的CH键官能化与多氟芳烃构建C（sp 2）C（sp 3）键的实用方法。从机理上讲，铜（I）卡宾的形成和随后的迁移插入被认为是反应途径中的关键步骤。
• A base-promoted cascade reaction of α,β-unsaturated <i>N</i>-tosylhydrazones with <i>o</i>-hydroxybenzyl alcohols: highly regioselective synthesis of <i>N-sec</i>-alkylpyrazoles
  作者：Lian-Mei Chen、Juan Zhao、An-Jie Xia、Xiao-Qiang Guo、Ya Gan、Chuang Zhou、Zai-Jun Yang、Jun Yang、Tai-Ran Kang

  DOI：10.1039/c9ob01780a

  日期：——

  N-sec-alkylpyrazoles through a base-promoted cascade cyclization/Michael addition reaction of α,β-unsaturated N-tosylhydrazones with ortho-hydroxybenzyl alcohols has been developed. The desired products containing di- or triaryl groups at the same carbon atom were afforded in good to excellent yields with excellent regioselectivities (>20 : 1). Moreover, a three-component reaction of ortho-hydroxybenzyl alcohols, α

  已经开发了一种通过α，β-不饱和N-甲苯磺酰with与邻羟基苄醇的碱促进的级联环化/ Michael加成反应合成N-仲烷基吡唑的有效方法。所提供的具有在相同碳原子上的二芳基或三芳基基团的期望产物以良好至优异的产率以及优异的区域选择性（＞ 20∶1）得到。此外，还进行了邻羟基苄醇，α，β-不饱和N-甲苯磺酰azo和饱和N-甲苯磺酰nes的三组分反应，以高收率得到吡唑。该反应以简单的操作提供了一条新的途径制备三芳基甲烷，适用于大规模合成。