methyl 1-(4-methoxyphenyl)ethylidenehydrazine carboxylate | 337924-89-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 1-(4-methoxyphenyl)ethylidenehydrazine carboxylate
• 英文别名: p-methoxyacetophenone methoxycarbonylhydrazone；N'-[1-(4-methoxyphenyl)ethylidene]methoxycarbohydrazide；methyl N-[1-(4-methoxyphenyl)ethylideneamino]carbamate
• CAS: 337924-89-7
• 化学式: C₁₁H₁₄N₂O₃
• mdl: MFCD00792949
• 分子量: 222.244
• InChiKey: FKXIEMKBZTWPIF-UHFFFAOYSA-N

物化性质

• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-(4-methoxyphenyl)ethylidenehydrazine carboxylate 在 溶剂黄146 、 三氟乙酸 作用下， 反应 216.0h， 生成 对甲氧基苯乙酮
  参考文献：
  名称：

  乙酰氧基（甲氧基）卡宾的非对映异构恶二唑啉源的合成和热分解速率常数——乙酰氧基（甲氧基）卡宾与异氰酸酯的反应

  摘要：

  对甲氧基苯乙酮的甲氧基羰基腙氧化得到顺式和反式-2-乙酰氧基-2-甲氧基-5-（对甲氧基苯基）-5-甲基-Δ3-1,3,4-恶二唑啉（也称为相应的2,5-二氢-1,3,4-恶二唑）以及 1-乙酰氧基-1-（对甲氧基苯基乙基）二氮烯羧酸甲酯。三种异构体通过光谱方法分离和鉴定。1-乙酰氧基-1-(对甲氧基苯基乙基)二氮烯羧酸甲酯是二氯甲烷中氧化的主要产物。在乙酸中氧化没有得到恶二唑啉，但得到二氮烯羧酸盐和另外的 1-(对甲氧基苯基)乙酸乙酯。通过酸催化将二氮烯羧酸异构化为恶二唑啉的尝试没有成功。恶二唑啉在 50.4 °C 下发生热解，速率常数大致相同（约 3. 6 × 10–5 s–1) 得到乙酰氧基（甲氧基）卡宾，其通过乙酰基转移重排为丙酮酸甲酯。卡宾与相对不受阻碍的异氰酸酯反应以转移...

  DOI：

  10.1139/v06-109
• 作为产物：
  描述：

  肼基甲酸甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 以 甲苯 为溶剂， 反应 5.0h， 生成 methyl 1-(4-methoxyphenyl)ethylidenehydrazine carboxylate
  参考文献：
  名称：

  Synthetic Entry into 1-Phosphono-3-azabicyclo[3.1.0]hexanes

  摘要：

  3-Azabicyclo[3.1.0]hex-2-en-1-yl phosphonates were prepared in a five-step reaction route from beta-ketophosphonates. The key steps in this sequence are an atom-transfer radical cyclization and an unforeseen lithium halogen exchange with n-BuLi. The cyclization reaction proceeds with excellent diastereoselectivity. The resulting cyclic imines were reduced, and 3-azabicyclo[3.1.0]hexan-1-yl phosphonates were obtained.

  DOI：

  10.1021/jo401185u

文献信息

• New Thermal Source of Dimethoxycarbene Leading to Zwitterionic Intermediates and 2:1 Stoichiometry in Reaction with Electrophilic Alkenes
  作者：Hongwei Zhou、Grzegorz Mloston、John Warkentin

  DOI：10.1021/ol040068+

  日期：2005.2.1

  [reaction: see text] At 50 degrees C, dimethyl dicyanofumarate and maleate react with 2 equiv of dimethoxycarbene to generate the products shown.

  [反应：见正文]在50摄氏度时，二氰基富马酸二甲酯和马来酸酯与2当量的二甲氧基卡宾反应生成所示产物。
• Formal Intramolecular (4 + 1)-Cycloaddition of Dialkoxycarbenes: Control of the Stereoselectivity and a Mechanistic Portrait
  作者：Francis Beaumier、Marianne Dupuis、Claude Spino、Claude Y. Legault

  DOI：10.1021/ja211927b

  日期：2012.4.4

  The stereoselective synthesis of 5-5, 6-5, and 7-5 fused O-heterocyclic compounds is reported. The key reaction is a formal intramolecular (4 + 1)-cycloaddition involving a dialkox-ycarbene and an electron-deficient diene where the stereo-selectivity is dependent on the length of the tether. An analysis of the stereochemical outcome of this reaction sheds light on its complex mechanistic picture. High-level calculations were used to support the proposed mechanistic portrait.
• Huff, Ann M.; Beam, Charles F., Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1343 - 1346
  作者：Huff, Ann M.、Beam, Charles F.

  DOI：——

  日期：——
• Synthetic Entry into 1-Phosphono-3-azabicyclo[3.1.0]hexanes
  作者：Wouter Debrouwer、Thomas S. A. Heugebaert、Kristof Van Hecke、Christian V. Stevens

  DOI：10.1021/jo401185u

  日期：2013.9.6

  3-Azabicyclo[3.1.0]hex-2-en-1-yl phosphonates were prepared in a five-step reaction route from beta-ketophosphonates. The key steps in this sequence are an atom-transfer radical cyclization and an unforeseen lithium halogen exchange with n-BuLi. The cyclization reaction proceeds with excellent diastereoselectivity. The resulting cyclic imines were reduced, and 3-azabicyclo[3.1.0]hexan-1-yl phosphonates were obtained.
• Synthesis and thermolysis rate constants of diastereomeric oxadiazoline sources of acetoxy(methoxy)carbene — Reaction of acetoxy(methoxy)carbene with isocyanates
  作者：Wojciech Sokol、John Warkentin

  DOI：10.1139/v06-109

  日期：2006.7.1

  catalysis were not successful. Thermolysis of the oxadiazolines at 50.4 °C occurred with approximately the same rate constant (ca. 3.6 × 10–5 s–1) to afford acetoxy(methoxy)carbene, which rearranges to methyl pyruvate by acetyl transfer. The carbene, which reacts with relatively unhindered isocyanates to transf...

  对甲氧基苯乙酮的甲氧基羰基腙氧化得到顺式和反式-2-乙酰氧基-2-甲氧基-5-（对甲氧基苯基）-5-甲基-Δ3-1,3,4-恶二唑啉（也称为相应的2,5-二氢-1,3,4-恶二唑）以及 1-乙酰氧基-1-（对甲氧基苯基乙基）二氮烯羧酸甲酯。三种异构体通过光谱方法分离和鉴定。1-乙酰氧基-1-(对甲氧基苯基乙基)二氮烯羧酸甲酯是二氯甲烷中氧化的主要产物。在乙酸中氧化没有得到恶二唑啉，但得到二氮烯羧酸盐和另外的 1-(对甲氧基苯基)乙酸乙酯。通过酸催化将二氮烯羧酸异构化为恶二唑啉的尝试没有成功。恶二唑啉在 50.4 °C 下发生热解，速率常数大致相同（约 3. 6 × 10–5 s–1) 得到乙酰氧基（甲氧基）卡宾，其通过乙酰基转移重排为丙酮酸甲酯。卡宾与相对不受阻碍的异氰酸酯反应以转移...