(E)-N′-octylidenebenzohydrazide

• 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′-octylidenebenzohydrazide
• 英文别名: N'-Octylidenebenzohydrazide；N-[(E)-octylideneamino]benzamide
• 化学式: C₁₅H₂₂N₂O
• 分子量: 246.352
• InChiKey: QGKCVWXXBFJINB-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 (E)-N′-octylidenebenzohydrazide 在 Mo₂(OAc)4 activated with O₂ 5A molecular sieve 、 甲醇 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以81%的产率得到N-(2-heptyl-4-oxo-2,3-dihydropyridin-1-yl)benzamide
  参考文献：
  名称：

  与分子氧激活的路易斯酸：酰基的aza-Diels-Alder反应的双核钼配合物。

  摘要：

  DOI：

  10.1002/anie.200600801
• 作为产物：
  描述：

  壬烯 、 苯甲酰肼 在 氧气 、 臭氧 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以33%的产率得到(E)-N′-octylidenebenzohydrazide
  参考文献：
  名称：

  Hydrazides of Organic Acids in the Transformations of the Peroxide Products of Non-1-ene Ozonolysis

  摘要：

  The reaction of hydrazides of alicyclic capric and aromatic benzoic and p-hydroxybenzoic acids with the peroxide product of non-1-ene ozonolysis was studied. Capric acid hydrazide exhibits the strongest reducing properties in aprotic solvents (methylene chloride, THF) and leads to chemoselective and high-yield (similar to 80%) formation of the corresponding acylhydrazone. p-Hydroxybenzoic acid hydrazide forms a similar derivative with a yield of 67% only in THF.

  DOI：

  10.1134/s1070428019110113

文献信息

• 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。
• 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。
• Chiral Sulfoxides as Neutral Coordinate-Organocatalysts in Asymmetric Allylation of <i>N</i>-Acylhydrazones Using Allyltrichlorosilanes
  作者：Shū Kobayashi、Chikako Ogawa、Hideyuki Konishi、Masaharu Sugiura

  DOI：10.1021/ja035061m

  日期：2003.6.1

  Sulfoxides were first introduced to the allylation of N-acylhydrazones with allyltrichlorosilanes as effective neutral coordinate-organocatalysts (NCOs). Both high diastereo- and enantioselectivity were attained when optically active chiral sulfoxides were used. Asymmetric crotylations using (Z)- and (E)-crotyltrichlorosilanes showed a high level of stereospecificity (Z --> anti and E --> syn) with

  亚砜首先被引入到 N-酰基腙与烯丙基三氯硅烷的烯丙基化反应中，作为有效的中性配位有机催化剂 (NCO)。当使用旋光手性亚砜时，可以获得高的非对映选择性和对映选择性。使用 (Z)- 和 (E)-巴豆基三氯硅烷的不对称巴豆化显示出高水平的立体特异性（Z --> anti 和 E --> syn），具有高对映选择性。
• With Molecular-Oxygen-Activated Lewis Acids: Dinuclear Molybdenum Complexes for Aza-Diels–Alder Reactions of Acyl Hydrazones
  作者：Yasuhiro Yamashita、Matthew M. Salter、Kayoko Aoyama、Shū Kobayashi

  DOI：10.1002/anie.200600801

  日期：2006.6.2
• Hydrazides of Organic Acids in the Transformations of the Peroxide Products of Non-1-ene Ozonolysis
  作者：Yu. V. Myasoedova、L. R. Garifullina、E. R. Nurieva、G. Yu. Ishmuratov

  DOI：10.1134/s1070428019110113

  日期：2019.11

  The reaction of hydrazides of alicyclic capric and aromatic benzoic and p-hydroxybenzoic acids with the peroxide product of non-1-ene ozonolysis was studied. Capric acid hydrazide exhibits the strongest reducing properties in aprotic solvents (methylene chloride, THF) and leads to chemoselective and high-yield (similar to 80%) formation of the corresponding acylhydrazone. p-Hydroxybenzoic acid hydrazide forms a similar derivative with a yield of 67% only in THF.