(E)-N'-(3-phenylpropylidene)benzohydrazide

• 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: (E)-N'-(3-phenylpropylidene)benzohydrazide
• 英文别名: Benzoic acid (3-phenyl-propylidene)-hydrazide；N-[(E)-3-phenylpropylideneamino]benzamide
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: YQBFBHSIZYCIDT-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (E)-N'-(3-phenylpropylidene)benzohydrazide 在 甲醇 、 六甲基磷酰三胺 、 copper(l) iodide 、 samarium diiodide 、 甲基锂 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 0.83h， 生成 3,3-dimethyl-4-(2'-phenylethyl)azetidin-2-one
  参考文献：
  名称：

  Mannich Type Reactions of Acylhydrazones with Silyl Enolates for the Synthesis of b-Amino Ester, b-Amino Ketone, b-Lactam, Pyrazolidinone, and Pyrazolone Derivatives

  摘要：

  DOI：

  10.3987/com-99-s113
• 作为产物：
  描述：

  苯丙醛 、 苯甲酰肼 以 甲醇 为溶剂， 以83%的产率得到(E)-N'-(3-phenylpropylidene)benzohydrazide
  参考文献：
  名称：

  自串联催化剂：通过带有功能配体的 Cp* 铱络合物催化的甲醇转移氢化/N-甲基化，从酰腙到 N',N'-甲基脂族酰肼

  摘要：

  提出并实现了以甲醇为氢源和甲基化试剂，通过转移氢化/ N-甲基化从酰肼合成N '，N'-甲基脂肪酰肼的新策略。在 [Cp*Ir(2,2'-bpyO)(H 2 O)]（1 mol %）和 Cs 2 CO 3（0.3 当量）的存在下，以高产率获得了一系列所需的产物。还证实了催化剂的 bpy 配体中的功能单元对铱配合物的催化活性至关重要。还介绍了本催化体系的机理研究和实际应用。

  DOI：

  10.1021/acs.orglett.2c03719

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。
• Indium(i) iodide-catalyzed regio- and diastereoselective formal α-addition of an α-methylallylboronate to N-acylhydrazones
  作者：Shū Kobayashi、Hideyuki Konishi、Uwe Schneider

  DOI：10.1039/b802153h

  日期：——

  Indium(I) iodide was found to catalyze the formal α-addition of an α-methylallylboronate to various N-acylhydrazones, in the presence of an alcohol additive, to afford the corresponding anti-α-adducts with high regio- and diastereoselectivity in high yields.

  铟(I)碘化物被发现能够催化α-甲基烯丙基硼酸酯与各种N-酰基肼酮的形式α-加成，在醇添加剂的存在下，获得相应的反式α-加成产物，具有高区域选择性和高立体选择性。
• Aza-Michael Addition Reactions of Hydrazones with Activated Alkynes Catalyzed by Nitrogen-Containing Organic Bases
  作者：Zhi-Liang Yuan、Yin Wei、Min Shi

  DOI：10.1002/ejoc.201000365

  日期：2010.7

  2]-octane)-catalyzed Michael-type reactions of hydrazones with activated alkynes are described in this paper. This aza-Michael addition reaction can be applied to different types of hydrazones, such as hydrazones 1 and hydroxy-bearing hydrazones 5. The corresponding adducts are achieved in high yields under mild reaction conditions. DABCO-promoted aza-Michael addition reactions were successfully applied to

  本文描述了几种高效的 DABCO（1,4-二氮杂双环 [2.2.2]-辛烷）催化腙与活化炔烃的迈克尔型反应。这种氮杂-迈克尔加成反应可以应用于不同类型的腙，如腙1和含羟基的腙5。相应的加合物在温和的反应条件下以高产率获得。DABCO 促进的氮杂-迈克尔加成反应成功地应用于一系列具有活化炔烃的腙，以中等至良好的产率提供相应的加合物。
• 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。