methyl α-(p-anisidinyimino acetate) | 24433-83-8

• 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 α-(p-anisidinyimino acetate)
• 英文别名: (1-methoxyethylidene)-N-(p-anisyl)amine；Methyl-N-(p-methoxyphenyl)-acetimidat；Methyl-N-p-methoxyphenylacetimidat；methyl N-(4-methoxyphenyl)ethanimidate
• CAS: 24433-83-8
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: QHKHOMHCXWBSKW-UHFFFAOYSA-N

物化性质

• 沸点：
  262.5±42.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl α-(p-anisidinyimino acetate) 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3R*,4R*)-3-(2-azidoethyl)-4-[(benzyloxymethoxy)methyl]-1-(4-methoxyphenyl)azetidin-2-one
  参考文献：
  名称：

  β-内酰胺的分子内氨基转移作为酶控制开环的手段：取代基对反应速率的影响

  摘要：

  已经合成了一系列带有氨基的带有侧链的简单单环β-内酰胺，并研究了它们的分子内酰胺化率。用酶可裂解基团保护氨基，使我们能够选择性地控制环的扩大过程。

  DOI：

  10.1016/s0040-4039(98)02118-2
• 作为产物：
  描述：

  S,S-dimethyl-N-(p-anisyl)sulfilimine 在 氧气 、 五羰基(1-甲氧基亚乙基)-铬 作用下， 以90%的产率得到methyl α-(p-anisidinyimino acetate)
  参考文献：
  名称：

  Reaction of chromium (Fischer) carbenes and sulfilimines

  摘要：

  The photochemical reactions of alkoxychromium (Fischer) carbenes and sulfilimines lead to imidates in fair to excellent yields. Aromatic, heteroaromatic, and alkylsulfilimines, the latter bearing functional groups such as cyano, sulfone, ether, ester, and dioxolane groups, gave the corresponding imidates in good to excellent yield. However, acyl- and sulfonyl-substituted sulfilimines did not react with chromium carbenes, except for sulfilimines bearing ethoxycarbonyl and phtalimidylamino groups. A variety of differently substituted chromium carbene complexes bearing alkyl, cycloalkyl, styryl, allyl, and alkynyl groups attached either at the carbene carbon or at the oxygen also gave imidates in good yields. For alpha,beta-unsaturated carbenes, the exclusive 1,2-addition of the sulfilimine nitrogen was observed at room temperature, in contrast to the behavior of other nitrogen nucleophiles which are reported to add in 1,4-fashion under these reaction conditions. In turn, optically active imidates of the type ArN=C(OR*)Me [R* = chiral substituent derived from (R)-(+)-1-phenyl-1-butanol, l-(-)-menthol, (1S)-endo-(-)-borneol, and (1R)-(-)-myrtenol] can be prepared efficiently by utilizing the corresponding chiral alkoxy group on the earbene moiety. The reactions above also occur in the dark but reaction times are considerably longer. N-Halosulfilimines reacted with alkoxychromium carbenes to yield N-acylsulfilimines instead of the expected N-haloimidates. Based upon a set of thermal and photochemical reactions between N-haloimidates and diphenyl sulfide in the absence of chromium complexes, the complex (CO)5CrNCMe is proposed to be responsible for this novel reaction of N-haloimidates and diphenyl sulfide.

  DOI：

  10.1021/jo00067a020

文献信息

• A new approach to N-aryl- and N-(2-heteroaryl)imidates from chromium carbenes and sulfilimines
  作者：Benito Alcaide、Gema Dominguez、Joaquin Plumet、Miguel A. Sierra

  DOI：10.1021/om00047a007

  日期：1991.1

  Irradiation of pentacarbonyl(alkoxymethylcarbene)chromium(0) complexes in the presence of a number of N-aryl- or N-heteroaryl-substituted sulfilimines gives N-aryl- or N-heteroarylimidates in fair to excellent yields.
• Pilotti,A. et al., Acta Chemica Scandinavica (1947), 1969, vol. 23, p. 818 - 824
  作者：Pilotti,A. et al.

  DOI：——

  日期：——
• Reaction of chromium (Fischer) carbenes and sulfilimines
  作者：Benito Alcaide、Luis Casarrubios、Gema Dominguez、Miguel A. Sierra

  DOI：10.1021/jo00067a020

  日期：1993.7

  The photochemical reactions of alkoxychromium (Fischer) carbenes and sulfilimines lead to imidates in fair to excellent yields. Aromatic, heteroaromatic, and alkylsulfilimines, the latter bearing functional groups such as cyano, sulfone, ether, ester, and dioxolane groups, gave the corresponding imidates in good to excellent yield. However, acyl- and sulfonyl-substituted sulfilimines did not react with chromium carbenes, except for sulfilimines bearing ethoxycarbonyl and phtalimidylamino groups. A variety of differently substituted chromium carbene complexes bearing alkyl, cycloalkyl, styryl, allyl, and alkynyl groups attached either at the carbene carbon or at the oxygen also gave imidates in good yields. For alpha,beta-unsaturated carbenes, the exclusive 1,2-addition of the sulfilimine nitrogen was observed at room temperature, in contrast to the behavior of other nitrogen nucleophiles which are reported to add in 1,4-fashion under these reaction conditions. In turn, optically active imidates of the type ArN=C(OR*)Me [R* = chiral substituent derived from (R)-(+)-1-phenyl-1-butanol, l-(-)-menthol, (1S)-endo-(-)-borneol, and (1R)-(-)-myrtenol] can be prepared efficiently by utilizing the corresponding chiral alkoxy group on the earbene moiety. The reactions above also occur in the dark but reaction times are considerably longer. N-Halosulfilimines reacted with alkoxychromium carbenes to yield N-acylsulfilimines instead of the expected N-haloimidates. Based upon a set of thermal and photochemical reactions between N-haloimidates and diphenyl sulfide in the absence of chromium complexes, the complex (CO)5CrNCMe is proposed to be responsible for this novel reaction of N-haloimidates and diphenyl sulfide.
• Intramolecular transamidation of β-lactams as a means for the enzymatic control of ring opening: Effect of substituents on the rate of reaction
  作者：Luca Banfi、Giuseppe Guanti、Marcello Rasparini

  DOI：10.1016/s0040-4039(98)02118-2

  日期：1998.12

  A series of simple monocyclic β-lactams bearing side-chains, containing amino groups, have been synthesized, and the rate of their intramolecular transamidation studied. Protection of the amino group with an enzymatically cleavable group, allows us to selectively control the ring enlargement process.

  已经合成了一系列带有氨基的带有侧链的简单单环β-内酰胺，并研究了它们的分子内酰胺化率。用酶可裂解基团保护氨基，使我们能够选择性地控制环的扩大过程。