1-苯甲酰基氮丙啶 | 7646-66-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苯甲酰基氮丙啶
• 英文名称: N-benzoylaziridine
• 英文别名: 1-benzoylaziridine；1-benzoyl-aziridine；1-Benzoyl-aziridin；1-(benzoyl)aziridine；(benzoyl)aziridine；aziridin-1-yl(phenyl)methanone
• CAS: 7646-66-4
• 化学式: C₉H₉NO
• 分子量: 147.177
• InChiKey: HGBCPYMIZWPKMI-UHFFFAOYSA-N

物化性质

• 熔点：
  8-9 °C
• 沸点：
  270.4±9.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-苯甲酰基氮丙啶 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 50.0 ℃ 、344.73 kPa 条件下， 反应 54.5h， 生成 N-[2-[2-(1H-imidazol-5-yl)ethylamino]ethyl]benzamide
  参考文献：
  名称：

  Cardiotonic agents. 6. Histamine analogs as potential cardiovascular selective H2 agonists

  摘要：

  Twenty-six alkyl and aralkyl histamine analogues were prepared as potential cardiotonic agents. Compounds were designed to allow interaction with a putative secondary aryl binding site at the H2 receptor, the presence of which was inferred from the structure of cyprohepatadine, which is known to have H2-antagonist properties. The compounds were examined for inotropic activity in ferret papillary muscle. Potent inotropic activity was generally found in N-alkyl- and N,N-dialkylimidazole-4-ethanamines, whereas N-(amidoalkyl)imidazole-4-ethanamines and N-alkylimidazole-4-propanamines were at best weakly active. Five compounds were examined in screens designed to assess hemodynamic effects and gastric acid secretion in vivo. Two of these compounds, alpha-(3-phenyl-2-transpropenyl)-1H-imidazole-4-ethanamine and N-heptyl-1H-imidazole-4-ethanamine, showed positive inotropic activity with minimal effects on heart rate and mean arterial pressure in vivo; however, both compounds were found to stimulate gastric acid secretion. These results demonstrate that selectivity between various H2-receptor-mediated activities can be obtained with substituted histamine analogues.

  DOI：

  10.1021/jm00168a024
• 作为产物：
  描述：

  N-(2-溴乙基)-苯甲酰胺 在 二氧化碳 、 氧气 、 高氯酸四乙基铵 作用下， 生成 1-苯甲酰基氮丙啶
  参考文献：
  名称：

  Electrogenerated Superoxide-Activated Carbon Dioxide. A New Mild and Safe Approach to Organic Carbamates

  摘要：

  The electrochemical reduction of O-2 (E = -1.0 V vs SCE) in dipolar aprotic solvents in the presence of CO2 gave a carboxylating reagent (O-2(.-)/CO2) able to convert amines and different types of their derivatives into carbamates. Primary and secondary aliphatic and aromatic amines were converted into the corresponding ethyl carbamates by the addition of EtI to the carbamate anions generated in the first step of the reactions. The yields were dependent on the nucleophilicity of the nitrogen atom. beta-Bromoethyl- and propylamine gave 2-oxazolidinone and tetrahydro-1,3-oxazin-2-one in moderate yields. N-Acyl or N-(alkoxycarbonyl)alkylamines bearing a leaving group at the beta position of the alkyl substituent were converted into 3-substituted-2-oxazolidinones in high yields. By using chiral substrates, enantiopure 3-alkoxycarbonyl(or acyl)-4-substituted oxazolidin-2-ones (70-85% isolated yields) were obtained. This represents a new mild and safe route to these important auxiliaries for asymmetric synthesis. Some limitations of the process are also evidenced and accounted for.

  DOI：

  10.1021/jo970308h

文献信息

• Reaction of 1-Lithio-1-arylthio(or alkylthio)methyltrimethylsilane with Acid Derivatives. A Novel Synthesis of Functionalized Vinyl Sulfides
  作者：Toshio Agawa、Minori Ishikawa、Mitsuo Komatsu、Yoshiki Ohshiro

  DOI：10.1246/bcsj.55.1205

  日期：1982.4

  Reactions of 1-lithio-1-phenylthiomethyl- (1a) and 1-lithio-1-methylthiomethyltrimethylsilane (1b) with amides, an ester, acid anhydrides, a urea, and a carbonate are described which provide useful routes to functionalized vinyl sulfides. The reaction of 1 with amides gave β-functionalized vinyl sulfides, 1-dialkylamino-2-phenylthio (or methylthio)ethylenes, in 40–95% yields and the reaction could

  描述了 1-锂硫基-1-苯硫基甲基-(1a) 和 1-锂硫基-1-甲硫基甲基三甲基硅烷 (1b) 与酰胺、酯、酸酐、脲和碳酸酯的反应，它们提供了用于官能化乙烯基硫化物的有用途径。1 与酰胺反应得到 β-官能化乙烯基硫化物，1-二烷基氨基-2-苯硫基（或甲硫基）乙烯，产率 40-95%，反应可以扩展到 1 的磺酰基衍生物，得到 1-二烷基氨基- 2-苯基磺酰基（或甲基磺酰基）乙烯。尽管苯甲酸乙酯和一些酸酐不是该反应的良好底物，但四甲基脲和碳酸二乙酯在用 1a 处理后以中等产率生成 α-官能化乙烯基硫化物、1-酰胺乙烯基和 1-（乙氧基羰基）乙烯基硫化物，然后加入苯甲醛。
• Reaktionen mit Aziridinen, 24. Mitt. Amidoethylierung monosubstituierter Malonester
  作者：Jochen Budny、Helmut Stamm

  DOI：10.1002/ardp.19813140802

  日期：——

  Phenylmalonester 1a und Methylmalonester 1b wurden unter verschiedenen Bedingungen mit den N‐Acylaziridinen 3a–e amidoethyliert. Nur in einem Falle (5) konnte das primär entstehende Amidoethylderivat als Nebenprodukt gefaßt werden, während dieses sonst offenbar vollständig zu den entsprechenden N‐Acylpyrrolidonen 6a–f cyclisierte, die ihrerseits meistens noch weiteren (alkoholytischen) Folgereaktionen

  苯基丙二酸酯 1a 和甲基丙二酸酯 1b 在不同条件下与 N-酰基氮丙啶 3a-e 进行酰胺乙基化。只有在一种情况 (5) 中，伯酰胺乙基衍生物可以作为副产物，而这显然完全环化为相应的 N-酰基吡咯烷酮 6a-f，而后者通常会进行进一步的（醇解）次级反应。
• A NOVEL SYNTHESIS OF VICINALLY N,S-DISUBSTITUTED OLEFINS FROM LITHIO SULFENYLTRIMETHYLSILYLMETHANE AND AMIDE
  作者：Toshio Agawa、Minori Ishikawa、Mitsuo Komatsu、Yoshiki Ohshiro

  DOI：10.1246/cl.1980.335

  日期：1980.3.5

  Vicinally N,S-disubstituted olefins are synthesized in good yields from amides by treating with lithio sulfenyltrimethylsilylmethanes.

  通过用锂硫磺基三甲基甲硅烷基甲烷处理，从酰胺以良好的收率合成了邻位 N,S-二取代烯烃。
• Homolytic aziridine opening (aza variant of cyclopropylcarbinyl-homoallyl rearrangement) by addition of tributyltin radical to N-acylaziridines. Factors contributing to the regioselectivity
  作者：Jürgen Werrya、Helmut Stamm、Pen-Yuan Lin、Reinhard Falkenstein、Stefan Gries、Hermann Irngartinger

  DOI：10.1016/s0040-4020(01)81081-4

  日期：1989.1

  fell drastically with steric hindrance of the addition of Bu3Sn. to the acyl oxygen of 1. They depended to some extent on the experimental conditions for hydrogen capturing when aziridine homolysis provided a primary radical 3 or 6. The regioselectivity of (probably reversible) ring homolysis can be understood in terms of the stability of the arising radical (3, 6), of stereoelectronic control (e.g. 1i

  AIBN在回流的苯中引发N-酰基丙啶1与Bu 3 SnH的反应，提供了还原性开环的产物5和8。由于添加了Bu 3 Sn的位阻，产率（大多数情况下是定量的）急剧下降。到1的酰基氧。他们在一定程度上取决于当氮丙啶均质分解提供伯自由基3或6时捕获氢的实验条件。的（可能是可逆的）环均裂区域选择性可以的产生自由基（稳定性的观点出发可以理解3，6），立体声电子控制（例如1i与1h相比）和边界轨道相互作用（1j）。从1j形成一级自由基的解释中，键长可能存在差异，但从N-甲苯磺酰基-2-甲基-氮丙啶11的X射线结构分析中未发现支持。异构体产物仅获得两次（1i，1j），比率5j：8j取决于Bu 3 SnH的浓度和氢同位素。没有发现比例为5:14的这种依赖关系（环化和无环化时减少3）由N-肉桂酰基氮丙啶11得到的吡咯烷酮。该比率（1：9为11和1：3为1N）必须反映在EZ异构体3。所观察到的由2形成E-3的偏
• Synthesis and Antibacterial Activities of Novel 4-Hydroxy-7-hydroxy- and 3-Carboxycoumarin Derivatives
  作者：Pen-Yuan Lin、Kuang-Sheng Yeh、Chien-Ling Su、Shiow-Yunn Sheu、Tiffany Chen、Keng-Liang Ou、Mei-Hsiang Lin、Lin-Wen Lee

  DOI：10.3390/molecules170910846

  日期：——

  used as fluorescent dyes and medicines. They also have some notable physiological effects, including the acute hepatoxicity and carcinogenicity of certain aflatoxins, the anticoagulant action of dicoumarol, and the antibiotic activity of novobicin and coumerymycin A1. Because the number of drug resistant strains is increasing at present, the synthesis of new antibacterial compounds is one of the critical

  香豆素衍生物用作荧光染料和药物。它们还具有一些显着的生理作用，包括某些黄曲霉毒素的急性肝毒性和致癌性、双香豆素的抗凝作用以及新生霉素和香豆素 A1 的抗菌活性。由于目前耐药菌株的数量不断增加，新的抗菌化合物的合成是治疗传染病的关键方法之一。因此，合成了一系列香豆素取代的衍生物，即4-羟基和7-羟基香豆素，以及3-羧基香豆素。4-羟基香豆素衍生物 4a-c 经历了重排反应。4- 和 7- 羟基香豆素都用活化的氮丙啶处理，产生了一系列开环产物 7、8、10 和 11。通过脂肪族烷基胺和烷基二胺与 PyBOP 和 DIEA 反应制备 3-羧基香豆素酰胺二聚体衍生物 14-21。在这项研究中，我们使用了一种称为改良微孔板抗生素药敏试验方法 (MMAST) 的新技术，该技术比以前的方法更方便、更高效、更准确，并且只需要少量样品即可进行检测。一些化合物是通过与酸酐反应产生的，并显示出抑制革兰氏阳性微生