methyl 2-(N,N-diphenylhydrazino)-3-methylbutanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(N,N-diphenylhydrazino)-3-methylbutanoate
• 英文别名: Methyl 2-(2,2-diphenylhydrazinyl)-3-methylbutanoate
• 化学式: C₁₈H₂₂N₂O₂
• 分子量: 298.385
• InChiKey: BVVGFGYCVJGEIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,1-二苯肼盐酸盐 在 indium 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成 methyl 2-(N,N-diphenylhydrazino)-3-methylbutanoate
  参考文献：
  名称：

  铟作为水介质中的自由基引发剂：分子间烷基加成CN和CC键

  摘要：

  通过使用铟作为单电子转移自由基引发剂，研究了在水介质中形成碳-碳键的方法。铟介导的亚胺衍生物的分子间烷基加成和电子缺陷的CC键有效地进行。

  DOI：

  10.1016/j.tet.2004.03.040

文献信息

• Evaluation of phenylorganotellurium compounds as radical precursors in dialkylzinc-mediated radical addition to CN double bonds
  作者：Fabien Cougnon、Laurence Feray、Samantha Bazin、Michèle P. Bertrand

  DOI：10.1016/j.tet.2007.09.014

  日期：2007.11

  Diethylzinc-mediated radical addition to CN bonds was investigated in the presence of phenylorganotellurium compounds as radical precursors. As group transfer agents, secondary alkyl phenyl tellurides were shown to be about twice as reactive as the corresponding alkyl iodides towards ethyl radical. Their use was proven to be advantageous regarding both chemoselectivity and yield. The replacement of

  在苯基有机碲化合物作为自由基前体的存在下，研究了二乙基锌介导的向CN键的自由基加成反应。作为基团转移剂，仲烷基苯基碲化物的反应活性约为相应的烷基碘对乙基的两倍。事实证明，它们的使用在化学选择性和产率方面都是有利的。用二甲基锌代替二乙基锌在这些反应中没有优势。
• Zinc-mediated carbon radical addition to glyoxylic imines in aqueous media for the synthesis of α-amino acids
  作者：Masafumi Ueda、Hideto Miyabe、Hisako Sugino、Takeaki Naito

  DOI：10.1039/b418726a

  日期：——

  glyoxylic imines was studied using zinc dust as a radical initiator. The zinc-mediated radical reaction of glyoxylic oxime ethers and hydrazones proceeded smoothly to give the alkylated products via a carbon-carbon bond-forming process in aqueous media. The reaction of the oxime ethers and hydrazones having an Oppolzer's camphorsultam group provided the corresponding alkylated products, which could be converted

  使用锌粉作为自由基引发剂，研究了向乙醛酸亚胺中添加碳自由基的方法。乙醛酸肟醚和的锌介导的自由基反应顺利进行，从而通过在水性介质中形成碳-碳键的方法得到烷基化产物。具有Oppolzer's樟脑素基团的肟醚和hydr的反应提供了相应的烷基化产物，可以将其转化为对映体纯的α-氨基酸。在hydr的反应中观察到的非对映选择性优于在肟醚的反应中获得的非对映选择性。
• Indium(I)-Mediated Radical Carbon-Carbon Bond-Forming Reaction in Aqueous Media
  作者：Okiko Miyata、Takeaki Naito、Masafumi Ueda、Hideto Miyabe、Masafumi Torii、Takahiro Kimura

  DOI：10.1055/s-0029-1219921

  日期：2010.6

  The carbon-carbon bond-forming radical reactions using indium(I) chloride and copper(I) chloride proceeded effectively through a single-electron transfer process in aqueous media.

  在水相介质中，通过单电子转移过程，使用氯化铟(I)和氯化铜(I)的碳-碳键形成自由基反应高效进行。
• Indium-Mediated Intermolecular Alkyl Radical Addition to Electron-Deficient CN Bond and CC Bond in Water
  作者：Hideto Miyabe、Masafumi Ueda、Azusa Nishimura、Takeaki Naito

  DOI：10.1021/ol017013h

  日期：2002.1.1

  see text] The intermolecular alkyl radical addition to imine derivatives was studied in aqueous media by using indium as a single-electron-transfer radical initiator. The one-pot reaction based on radical addition to glyoxylic hydrazone provided a convenient method for preparing the alpha-amino acids. The indium-mediated radical addition to an electron-deficient C=C bond also proceeded effectively to

  [反应：见正文]通过使用铟作为单电子转移自由基引发剂，在水性介质中研究了亚胺衍生物的分子间烷基加成反应。基于自由基加成至乙醛酸的一锅法反应提供了一种方便的制备α-氨基酸的方法。铟介导的自由基向电子缺乏的C = C键的加成也有效地进行，以提供在水性介质中形成新的碳-碳键的方法。
• Diethylzinc: A Chain-Transfer Agent in Intermolecular Radical Additions. A Parallel with Triethylborane
  作者：Michèle P. Bertrand、Laurence Feray、Robert Nouguier、P. Perfetti

  DOI：10.1021/jo9912404

  日期：1999.12.1

  In the presence of oxygen, diethylzinc can be used to promote radical additions to C=N bond containing radical accepters and to enones. In these reactions, it plays at the same time the role of the initiator and the role of the chain-transfer reagent. A parallel with triethylborane-mediated reactions is established. The methodology is restricted to secondary and tertiaryalkyl radicals generated from the corresponding alkyl iodides. It could not be extended either to C=C bond containing radical accepters such as methyl methacrylate and nitrocyclohexene or to diethylazodicarboxylate.