isovaleraldehyde benzoylhydrazone

• 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: isovaleraldehyde benzoylhydrazone
• 英文别名: (E)-N′-(3-methylbutylidene)benzohydrazide；(E)-N'-(3-methylbutylidene)benzohydrazide；N-[(E)-3-methylbutylideneamino]benzamide
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: PWRGKTBVGYKYEA-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  isovaleraldehyde benzoylhydrazone 在 三氟化硼乙醚 、 烯丙基三甲基硅烷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.08h， 生成
  参考文献：
  名称：

  Trifluoromethylation of N-Benzoylhydrazones

  摘要：

  A method for the nucleophilic trifluoromethylation of N-benzoylhydrazones using Me3SiCF3/AcONa has been described. The C=N bond of the hydrazones is activated by difluoroboron group, which is introduced by means of boron trifluoride and allylsilane.

  DOI：

  10.1021/jo800782w
• 作为产物：
  描述：

  苯甲酰肼 、 异戊醛 在 四氢吡咯 作用下， 以 水 为溶剂， 反应 2.0h， 生成 isovaleraldehyde benzoylhydrazone
  参考文献：
  名称：

  在温和的有机催化反应条件下可持续合成肟，Hy和硫代氨基脲

  摘要：

  吡咯烷很有效地催化，大概是通过亚胺基活化，使用等摩尔量的试剂和绿色溶剂，形成了芳香族和脂肪族醛衍生的酰基肟，酰基hydr和硫代半氨基甲酮。该方法的主要优点是实验简单，过滤简单后的优异收率，是目前可用于那些特别是酰基衍生物的替代方法，这些方法在未催化条件下不起作用。通过醛和酰基羟胺之间的直接缩合将其用于合成酰基肟的应用是空前的。

  DOI：

  10.1021/acs.joc.6b01912

文献信息

• Lewis Acid-Catalyzed Allylation Reactions of Acylhydrazones with Tetraallyltin in Aqueous Media
  作者：Shū Kobayashi、Tomoaki Hamada、Kei Manabe

  DOI：10.1055/s-2001-15166

  日期：——

  Allylation reactions of various benzoylhydrazones with tetraallyltin were found to proceed smoothly in the presence of scandium triflate as a Lewis acid catalyst at ambient temperature in aqueous media, to afford the corresponding homoallylic amine derivatives in high yields. Three-component reactions of aldehydes, benzoylhydrazine, and tetraallyltin were also catalyzed by scandium triflate in the same media. Furthermore, a simple procedure to prepare oxazolidinone derivatives utilizing these reactions was developed.

  在水相介质中，在三氟甲磺酸钪作为路易斯酸催化剂的存在下，多种苯甲酰肼与四烯基锡的烯化反应在室温下顺利进行，以高产率生成相应的同烯丙基胺衍生物。醛、苯甲酰肼和四烯基锡的三组分反应也可以在相同介质中通过三氟甲磺酸钪催化。此外，还开发了一种利用这些反应制备恶唑啉酮衍生物的简单方法。
• Catalytic asymmetric aza Diels–Alder reactions of hydrazones using a chiral zirconium catalyst
  作者：Yasuhiro Yamashita、Yumiko Mizuki、Shū Kobayashi

  DOI：10.1016/j.tetlet.2005.01.111

  日期：2005.3

  Catalytic asymmetric aza Diels–Alder reactions of acylhydrazones with Danishefsky’s dienes have been developed. A chiral zirconium complex derived from zirconium propoxide and 3,3′,6,6′-I4BINOL was found to be effective in this reaction, and the desired optically active 2,3-dihydro-4-pyridone derivatives were obtained with high enantioselectivities. Asymmetric formal synthesis of a natural product

  已开发了酰基hydr与Danishefsky二烯的催化不对称氮杂Diels-Alder反应。已发现衍生自丙氧化锆和3,3'，6,6'-I 4 BINOL的手性锆络合物在该反应中有效，并以高收率获得了所需的旋光性2,3-二氢-4-吡啶酮衍生物对映选择性。使用该催化不对称反应作为关键步骤，进行了天然产物香氨酸的不对称形式合成。
• Rare Earth Triflate-Catalyzed Addition Reactions of Acylhydrazones with Silyl Enolates. A Facile Synthesis of Pyrazolone Derivatives
  作者：Hidekazu Oyamada、Shu Kobayashi

  DOI：10.1055/s-1998-1638

  日期：1998.3

  In the presence of a catalytic amount of a rare earth triflate, benzoylhydrazones reacted with silyl enolates to afford the corresponding β-N′-benzoylhydrazino esters in high yields. The hydrazino esters thus obtained were readily converted to pyrazolone derivatives by treatment with a base. A three-component reaction between an aldehyde, an acylhydrazine, and a silyl enolate was also performed successfully.

  在一定量的稀土三酸盐催化下，苯甲酰肼与硅烯酸酯发生反应，生成相应的δ-N′-苯甲酰肼酯，产率很高。由此获得的肼酯经碱处理后很容易转化为吡唑酮衍生物。此外，还成功地进行了醛、酰基肼和硅烷基烯醇的三组分反应。
• Zirconium-Catalyzed Enantioselective [3+2] Cycloaddition of Hydrazones to Olefins Leading to Optically Active Pyrazolidine, Pyrazoline, and 1,3-Diamine Derivatives
  作者：Yasuhiro Yamashita、Shū Kobayashi

  DOI：10.1021/ja049498l

  日期：2004.9.1

  conducted in high yields with high enantioselectivities using a chiral zirconium catalyst. These reactions open ways to synthetically and biologically important pyrazoline, pyrazolidine, and 1,3-diamine derivatives. Further, several experiments suggested that the reactions proceeded via concerted pathways.

  使用手性锆催化剂，腙与外部烯烃的不对称 [3+2] 环加成反应以高产率和高对映选择性成功进行。这些反应为合成和生物学上重要的吡唑啉、吡唑烷和 1,3-二胺衍生物开辟了道路。此外，一些实验表明反应是通过协同途径进行的。
• Cyanation ofN-Acylhydrazones with Trimethylsilyl Cyanide Promoted by a Brønsted Base and a Lewis Acid
  作者：Hideyuki Konishi、Chikako Ogawa、Masaharu Sugiura、Shū Kobayashi

  DOI：10.1002/adsc.200505272

  日期：2005.12

  Cyanation of N-acylhydrazones using trimethylsilyl cyanide (TMSCN) proceeded well in the presence of an amine to afford the corresponding α-hydrazinonitriles in high yields. For less reactive substrates, the combined use of an amine and a catalytic amount of scandium triflate [Sc(OTf)3] was effective to promote the reactions. The mechanistic study suggested that the amine worked as a Brønsted base

  的氰化Ñ -acylhydrazones使用胺，得到相应的α-hydrazinonitriles高产率的存在下进行以及三甲基硅烷基氰化物（TMSCN）。对于反应性较低的底物，胺和催化量的三氟甲磺酸[[Sc（OTf）3 ]的组合使用可有效促进反应。机理研究表明，胺作为布朗斯台德碱起作用。