diethyl 1-(1-phenylethyl)-1,2-hydrazinedicarboxylate | 94203-19-7

• 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: diethyl 1-(1-phenylethyl)-1,2-hydrazinedicarboxylate
• 英文别名: (1-phenyl-ethyl)-hydrazine-N,N'-dicarboxylic acid diethyl ester；(1-Phenyl-aethyl)-hydrazin-N,N'-dicarbonsaeure-diaethylester；Diethyl 1-(1-phenylethyl)hydrazine-1,2-dicarboxylate；ethyl N-(ethoxycarbonylamino)-N-(1-phenylethyl)carbamate
• CAS: 94203-19-7
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: IXDVZHTZLPWFKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 1-(1-phenylethyl)-1,2-hydrazinedicarboxylate 、 溴乙酸甲酯 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 以96%的产率得到Methyl 2-[ethoxycarbonyl-[ethoxycarbonyl(1-phenylethyl)amino]amino]acetate
  参考文献：
  名称：

  用二乙氧基羰基肼衍生物通过E1cB裂解N-N′-键而不是还原来合成氨基甲酸酯

  摘要：

  在50°C下用溴乙酸甲酯/ Cs 2 CO 3 / MeCN处理二乙氧基羰基肼衍生物，然后加热至80°C，导致N-N '键裂解为相应的氨基甲酸酯。

  DOI：

  10.1021/ol902313v
• 作为产物：
  描述：

  ethyl N-(ethoxycarbonylamino)-N-[1-[1-[ethoxycarbonyl-(ethoxycarbonylamino)amino]cyclohexa-2,5-dien-1-yl]ethyl]carbamate 生成 diethyl 1-(1-phenylethyl)-1,2-hydrazinedicarboxylate
  参考文献：
  名称：

  JA, OBSON, B. M.;ARVANITIS, G. M.;ELIASENT, C. A.;MITELMAN, R., J. ORG. CHEM., 1985, 50, N 2, 194-201

  摘要：

  DOI：

文献信息

• <i>N</i>-Hydroxybenzimidazole as a structurally modifiable platform for <i>N</i>-oxyl radicals for direct C–H functionalization reactions
  作者：Tomomi Yoshii、Saori Tsuzuki、Shunya Sakurai、Ryu Sakamoto、Julong Jiang、Miho Hatanaka、Akira Matsumoto、Keiji Maruoka

  DOI：10.1039/d0sc02134b

  日期：——

  Methods for direct functionalization of C–H bonds mediated by N-oxyl radicals constitute a powerful tool in modern organic synthesis. While several N-oxyl radicals have been developed to date, the lack of structural diversity for these species has hampered further progress in this field. Here we designed a novel class of N-oxyl radicals based on N-hydroxybenzimidazole, and applied them to the direct C–H functionalization

  由N-氧基自由基介导的 C-H 键直接官能化方法构成了现代有机合成的有力工具。虽然迄今为止已经开发了几种N-氧基自由基，但这些物种缺乏结构多样性阻碍了该领域的进一步进展。在这里，我们设计了一类基于N-羟基苯并咪唑的新型N-氧基自由基，并将其应用于直接的 C-H 官能化反应。这些结构的灵活可修改特性使得能够轻松调整其催化性能。此外，利用这些有机自由基，我们开发了一种无金属方法来合成酰基氟，通过在温和条件下醛的直接 C-H 氟化。
• Radical Amination of C(sp³)–H Bonds Using <i>N</i>-Hydroxyphthalimide and Dialkyl Azodicarboxylate
  作者：Yuuki Amaoka、Shin Kamijo、Tamaki Hoshikawa、Masayuki Inoue

  DOI：10.1021/jo301840e

  日期：2012.11.16

  A direct conversion of C(sp(3))-H bonds to C(sp3)-N bonds has been achieved by utilizing catalytic N-hydroxyphthalimide (NHPI) and stoichiometric dialkyl azodicarboxylate. NHPI functions as a precursor of the electron-deficient phthalimide N-oxyl radical (PINO) to abstract hydrogens, and dialkyl azodicarboxylate acts as a trapping agent of the resultant carbon radical to generate the hydrazine derivatives. This C-H amination proceeds in a highly chemoselective manner with a wide applicability to functionalize benzylic, propargylic, and aliphatic C-H bonds. Furthermore, the obtained hydrazine compounds were readily converted to the corresponding carbamates or amines. Hence, the present protocol for direct introduction of the nitrogen functionality serves as a powerful tool for efficient construction of nitrogen-substituted natural products and pharmaceuticals.
• Selective Functionalization of Hydrocarbons Using a ppm Bioinspired Molecular Tweezer via Proton-Coupled Electron Transfer
  作者：Hongyu Chen、Lingling Wang、Sheng Xu、Xiaohui Liu、Qian He、Lijuan Song、Hongbing Ji

  DOI：10.1021/acscatal.1c01350

  日期：2021.6.18
• Huisgen et al., Justus Liebigs Annalen der Chemie, 1954, vol. 590, p. 1,31
  作者：Huisgen et al.

  DOI：——

  日期：——
• Ene reactions of conjugated dienes. 2. Dependence of rate on degree of hydrogen removed and s-cis or s-trans diene character
  作者：Barry M. Jacobson、Georgia M. Arvanitis、Carol A. Eliasen、Rimma Mitelman

  DOI：10.1021/jo00202a011

  日期：1985.1