(1,2-diphenylethylidene)hydrazine | 5171-96-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1,2-diphenylethylidene)hydrazine
• 英文别名: 1,2-diphenylethanone hydrazone；1-hydrazono-1,2-diphenylethane；Phenyl benzyl ketone hydrazone；hydrazone of deoxybenzoin；deoxybenzoin hydrazone；benzyl phenyl ketone hydrazone；Ethanone, 1,2-diphenyl-, hydrazone；1,2-diphenylethylidenehydrazine
• CAS: 5171-96-0
• 化学式: C₁₄H₁₄N₂
• 分子量: 210.279
• InChiKey: DWLXCNYLTHJPEU-UHFFFAOYSA-N

物化性质

• 熔点：
  156 °C
• 沸点：
  373.2±35.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1,2-diphenylethylidene)hydrazine 在 iodine monofluoride 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以55%的产率得到(1,1-二氟-2-苯基乙基)苯
  参考文献：
  名称：

  Conversion of the carbonyl group to CF2 using iodine monofluoride (IF)

  摘要：

  A novel method for the transformation of CO --> CF2 is described. The easily made hydrazone derivatives of the carbonyl moiety are reacted under mild conditions with IF prepared directly from the corresponding elements. Various hydrazones have been examined and compared with each other. Unsubstituted ones are usually the most suitable although they are not always easy to purify and store. N-Methyl- and N,N-dimethylhydrazones also give quite satisfactory results. The more easily made dinitrophenyl hydrazones (DNPs), semicarbazones, and tosylhydrazones also react, but the yields of the desired CF2 compounds are usually lower. Oximes could also be successfully reacted. The two main byproducts of the reaction are the parent carbonyl compounds, which can be recycled, and the alpha-iododifluoro derivatives. The latter upon treatment with LiAlH4 or Bu3SnH were reduced to the desired product, thus increasing the overall yields.

  DOI：

  10.1021/jo00015a024
• 作为产物：
  描述：

  二苯基乙炔 在 C₁₉H₂₈AuClN₂ 、 肼 作用下， 以 氘代氯仿 为溶剂， 反应 6.0h， 以82%的产率得到(1,2-diphenylethylidene)hydrazine
  参考文献：
  名称：

  Anti-Bredt N-杂环卡宾：一种有效的配体，用于金（I）催化末端炔烃与母体肼的加氢胺化。

  摘要：

  通过利用自由卡宾可逆地插入六甲基二硅氮烷的NH键中，合成了抗Bredt N-杂环卡宾金（I）氯化物络合物。该预催化剂在室温下促进末端炔烃的母体肼加氢胺化。

  DOI：

  10.1039/c3cc41279b

文献信息

• Gold-Catalyzed Hydroamination of Alkynes and Allenes with Parent Hydrazine
  作者：Rei Kinjo、Bruno Donnadieu、Guy Bertrand

  DOI：10.1002/anie.201100740

  日期：2011.6.6

  A diverse array of nitrogen‐containing compounds were formed by the addition of hydrazine to alkynes, diynes, enynes, and allenes in the presence of cationic gold(I) complexes with a cyclic (alkyl)(amino)carbene ligand (see scheme; the X‐ray crystal structure of the gold–hydrazine complex is shown). This hydroamination is an ideal initial step for the preparation of acyclic and heterocyclic bulk chemicals

  在具有环状（烷基）（氨基）卡宾配体的阳离子金（I）配合物存在下，将肼添加到炔烃，二炔，烯炔和丙二烯中，形成了多种含氮化合物（请参见方案；显示了金-肼配合物的X射线晶体结构）。该加氢胺化是制备无环和杂环本体化学品的理想初始步骤。浸渍= 2,6-二异丙基苯基。
• An efficient synthesis of isoquinolines via rhodium-catalyzed direct C–H functionalization of arylhydrazines
  作者：Sai Zhang、Daorui Huang、Guangyang Xu、Shengyu Cao、Rong Wang、Shiyong Peng、Jiangtao Sun

  DOI：10.1039/c5ob01171j

  日期：——

  Rhodium-catalyzed C–H bond activation of arylhydrazines and coupling with internal alkynes has been realized.

  铑催化的芳基肼的C-H键活化并与内部炔烃偶联已经实现。
• Regioselective One-Step Synthesis of Pyrazoles from Alkynes and N-Tosylhydrazones: [3+2] Dipolar Cycloaddition/[1,5] Sigmatropic Rearrangement Cascade
  作者：M. Carmen Pérez-Aguilar、Carlos Valdés

  DOI：10.1002/anie.201301284

  日期：2013.7.8

  Rearrangement under control: A wide variety of 3,4,5‐ and 1,3,5‐trisubstituted pyrazoles can be prepared from tosylhydrazones of ketones and terminal alkynes through the title reaction sequence (see scheme; Ts=4‐toluenesulfonyl). The rearrangement, and therefore, the regioselectivity of the reaction is controlled by the nature of the substituents of the tosylhydrazone.

  在控制下进行重排：可以通过标题反应顺序（参见方案； Ts = 4-甲苯磺酰基），从酮和末端炔烃的甲苯磺酰prepared制备各种各样的3,4,5-和1,3,5-三取代的吡唑。反应的重排以及因此的区域选择性由甲苯磺酰hydr的取代基的性质控制。
• Sulphur promoted C(sp³)–C(sp²) cross dehydrogenative cyclisation of acetophenone hydrazones with aldehydes: efficient synthesis of 3,4,5-trisubstituted 1H-pyrazoles
  作者：Rajeshwer Vanjari、Tirumaleswararao Guntreddi、Saurabh Kumar、Krishna Nand Singh

  DOI：10.1039/c4cc08210a

  日期：——

  A novel strategy for the cross dehydrogenative coupling (CDC) of acetophenone hydrazones and aldehydes has been developed for the synthesis of highly substituted pyrazoles. This work, for the first time, uses elemental sulfur as a promoter as well as a hydrogen acceptor in effecting the Csp(3)-Csp(2) bond formation via C-H activation.

  苯乙酮hydr和醛类的交叉脱氢偶联（CDC）的新策略已经开发出来，用于合成高度取代的吡唑。这项工作第一次使用元素硫作为促进剂以及氢受体，以通过CH活化作用实现Csp（3）-Csp（2）键的形成。
• Anti-Bredt N-heterocyclic carbene: an efficient ligand for the gold(i)-catalyzed hydroamination of terminal alkynes with parent hydrazine
  作者：María J. López-Gómez、David Martin、Guy Bertrand

  DOI：10.1039/c3cc41279b

  日期：——

  An anti-Bredt N-heterocyclic carbene gold(I) chloride complex was synthesized by taking advantage of the reversible insertion of the free carbene into the NH bond of hexamethyldisilazane. This precatalyst promotes the parent hydrazine hydroamination of terminal alkynes at room temperature.

  通过利用自由卡宾可逆地插入六甲基二硅氮烷的NH键中，合成了抗Bredt N-杂环卡宾金（I）氯化物络合物。该预催化剂在室温下促进末端炔烃的母体肼加氢胺化。