methyl (diphenylmethylene)carbamate | 36728-22-0

• 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: methyl (diphenylmethylene)carbamate
• 英文别名: N-methoxycarbonylbenzophenone imine；N-(Diphenylmethylen)carbamidsaeure-methylester；benzophenone glycine imine methyl ester；methyl N-benzhydrylidenecarbamate
• CAS: 36728-22-0
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: SCQMIJMDZRPKBE-UHFFFAOYSA-N

物化性质

• 沸点：
  356.7±25.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 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：
  38.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (diphenylmethylene)carbamate 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以60%的产率得到N-methoxycarbonyl-3,3-diphenyloxaziridine
  参考文献：
  名称：

  N-Alkyloxycarbonyl-3-aryloxaziridines: Their Preparation, Structure, and Utilization As Electrophilic Amination Reagents

  摘要：

  AbstractThis paper reports the synthesis of a series of N‐protected oxaziridines (N‐Moc, Boc, Z or Fmoc) and discusses their ability to deliver their N‐alkoxycar‐bonyl fragment to amines, enolates, sulfur, and phosphorus nucleophiles (electrophilic amination). These oxaziridines are prepared by oxidation of the corresponding imines with oxone or anhydrous MCPBA lithium salt as the source of oxygen. They transfer their N‐protected fragment to primary and secondary amines to give protected hydrazines in fair to excellent yield. The nitrogen transfer to free amino acids (in form of their R4N+ salts) is particularly fast, even at low temperature, providing L (or D) N‐protected α‐hydrazino acids. Enolates are C‐aminated to give N‐protected α‐amino ketones, esters, or amides in modest yield, due to a side aldol reaction of the unreacted enolate with the released benzaldehyde. With tertiary amines (Et3N), sulfides (PhSMe), and phosphines (Ph3P), amination and oxidation proceed in a parallel way; the amount of amination product increases when the temperature is lowered (kinetic control). Some of the factors that can orient the oxaziridine reactivity towards amination or oxidation of nucleophiles are considered.

  DOI：

  10.1002/chem.19970031019
• 作为产物：
  描述：

  methyl-2-(((diphenylmethylene)amino)oxy)-2-oxoacetate 在 9-噻吨酮 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以72%的产率得到methyl (diphenylmethylene)carbamate
  参考文献：
  名称：

  烯烃和（杂）芳烃光化学单步合成 β-氨基酸衍生物

  摘要：

  β-氨基酸经常被发现是许多生物活性分子、药物和天然产物中的重要成分。特别是，由于它们提高了代谢稳定性，它们被广泛用于构建生物活性肽和肽模拟物。尽管建立了许多用于制备 β-氨基酸衍生物的方法，但这些方法中的大多数都需要金属介导的预功能化底物的多步操作。在这里，我们公开了一种无金属、能量转移的高区域选择性分子间氨基羧化反应，用于将胺和酯官能团单步安装到烯烃或（杂）芳烃中。开发了一种双功能肟草酸酯以同时产生以 C 为中心的酯和以 N 为中心的亚氨基自由基。

  DOI：

  10.1038/s41557-022-01008-w

文献信息

• Synthesis and spectra of aldehyde- and ketone-<i>O</i>-(2,5-dihydro-2-methoxy-5,5-dimethyl-1,3,4-oxadiazol-2-yl)oximes — Thermal sources of some methoxy(oximino)carbenes
  作者：Arkadiusz Klys、Malgorzata Dawid、John Warkentin

  DOI：10.1139/v05-061

  日期：2005.5.1

  compounds were characterized by means of spectroscopy and the formation of carbenes upon thermolysis of a few was demonstrated by means of interception with tert-butyl alcohol. The carbenes fragmented to form methoxycarbonyl and iminyl radicals.Key words: 2,2-dioxyoxadiazoline, methoxy(oximino)carbene, oxadiazole, radical pair, rearrangement.

  通过将 2-乙酰氧基-2-甲氧基-Δ3-1,3,4-恶二唑啉的乙酰氧基与肟基交换，合成了十种新的甲氧基（肟基）卡宾的恶二唑啉来源。新化合物通过光谱学表征，并且通过用叔丁醇拦截证明了在一些热解时形成卡宾。卡宾断裂形成甲氧基羰基和亚胺基。关键词：2,2-二氧恶二唑啉，甲氧基（肟基）卡宾，恶二唑，自由基对，重排。
• Process for the preparation of a benzophenone glycine imine alkyl ester derivative
  申请人：Bayer CropScience AG

  公开号：EP1967511A1

  公开（公告）日：2008-09-10

  Process for the preparation of a benzophenone glycine imine alkyl ester derivative of general formula (I) :

  制备一种通式（I）的苯甲酮甘氨酸亚胺烷基酯衍生物的过程：
• A Facile Method for the Synthesis of Substituted<i>N</i>-Methylenecarboxamides and Alkyl<i>N</i>-Methylenecarbamates
  作者：Rainer Kupfer、Stefan Meier、Ernst-Ulrich Würthwein

  DOI：10.1055/s-1984-30936

  日期：——
• Mochalin, V. B.; Khenkina, T. V., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 583
  作者：Mochalin, V. B.、Khenkina, T. V.

  DOI：——

  日期：——
• MOCHALIN, V. B.;XENKINA, T. V., ZH. ORGAN. XIMII, 1982, 18, N 3, 672-673
  作者：MOCHALIN, V. B.、XENKINA, T. V.

  DOI：——

  日期：——