(8ci,9ci)-1H-氮杂卓-1-羧酸甲酯 | 17870-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 中文名称: (8ci,9ci)-1H-氮杂卓-1-羧酸甲酯
• 英文名称: N-methoxycarbonyl-1H-azepine
• 英文别名: azepine-1-carboxylic acid methyl ester；1H-Azepine-1-carboxylic acid methyl ester；methyl azepine-1-carboxylate
• CAS: 17870-94-9
• 化学式: C₈H₉NO₂
• 分子量: 151.165
• InChiKey: ZPTRHMXCWJANQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (8ci,9ci)-1H-氮杂卓-1-羧酸甲酯 在 四丁基高氯酸铵 作用下， 以 乙腈 为溶剂， 以79%的产率得到N-苯基香豆甲酯
  参考文献：
  名称：

  Kondo, Satoru; Suzuki, Hiroshi; Hattori, Tatsuya, Heterocycles, 1998, vol. 48, # 6, p. 1151 - 1156

  摘要：

  DOI：
• 作为产物：
  描述：

  苯 、 叠氮基甲酸甲酯 生成 (8ci,9ci)-1H-氮杂卓-1-羧酸甲酯
  参考文献：
  名称：

  腈与1H-氮杂环庚烷衍生物的新反应：2,6-二氮杂双环[3.3.0]辛二烯和2,8-二氮杂双环[3.2.1]辛二烯的形成

  摘要：

  氮杂高氮平的中间体阐明了两个二氮杂双环辛二烯（和）的形成。

  DOI：

  10.1016/s0040-4039(00)81902-4

文献信息

• Cycloaddition Reactions of Azepines and Diazepines with Conjugated Double Bonds Possessing Electron-Withdrawing Groups
  作者：Katsuhiro Saito、Shigenori Iida、Toshio Mukai

  DOI：10.1246/bcsj.57.3483

  日期：1984.12

  Cycloadditions of 1-ethoxycarbonyl-1H-azepine with 5-methoxycarbonyl-2-pyrone gave [4+2] and [4+6] type adducts and a benzazepine derivative, while the reaction of the azepine derivative with 3-methoxycarbonyl-2-pyrone afforded only a [4+2] type adduct. Similarly, an addition of 1-ethoxycarbonyl-1H-1,2-diazepine with 5-methoxycarbonyl-2-pyrone gave a benzodiazepine derivative. Reactions of the azepine

  1-乙氧羰基-1H-氮杂与 5-甲氧羰基-2-吡喃酮的环加成得到 [4+2] 和 [4+6] 型加合物和苯并氮杂衍生物，而氮杂衍生物与 3-甲氧羰基-2-吡喃酮仅提供 [4+2] 型加合物。类似地，1-乙氧基羰基-1H-1,2-二氮杂与5-甲氧羰基-2-吡喃酮的加成得到苯二氮杂衍生物。氮杂和二氮杂衍生物与四氯环戊二烯酮二甲基乙缩醛反应得到[4+2]型加合物。
• Reactions of co-ordinated ligands. Part 15. The cycloaddition of electronegatively substituted unsaturated systems to tricarbonyl(η-N-methoxycarbonyl-1H-azepine)-iron and -ruthenium and tricarbonyl(η-cyclohepta-2,4,6-trien-1-one)iron
  作者：Michael Green、Susan M. Heathcock、Terence W. Turney、D. Michael P. Mingos

  DOI：10.1039/dt9770000204

  日期：——

  Hexafluoroacetone, tetracyanoethylene, and 1,1 dicyano-2,2-bis(trifluoromethyl)ethyiene form exo-1,3 adducts with tricarbonyl(η-cyclohepta-2,4,6-trien-1-one)iron and tricarbonyl(η-N-methoxycarbonyl-1H-azepine)-iron and -ruthenium. A 1,6 adduct is also obtained with the azepineiron system. Deuteriation experiments show that the unco-ordinated double bond is the initial site of electrophilic attack.

  六氟丙酮，四氰基乙烯和1,1二氰基-2,2-双（三氟甲基）乙炔与三羰基（η-环庚-2,4,6-三烯-1-酮）铁和三羰基（η ）形成exo -1,3加合物- ñ甲氧基羰基-1- ħ吖庚因） -铁和钌。用氮杂铁体系也可得到1，6加合物。氘化实验表明，未配位的双键是亲电子攻击的起始位点。环庚三烯酮铁络合物的1,3-四氰基乙烯加合物在溶液中容易异构化为1,5-加合物。严格评估了这些环加成反应的公认偶极机理，并提出了另一种协调一致的反应路径。
• Chromium(0) promoted [6π+2π] cycloaddition reactions
  作者：James H. Rigby、Humy S. Ateeq、Nelly R. Charles、James A. Henshilwood、Kevin M. Short、Priyantha M. Sugathapala

  DOI：10.1016/s0040-4020(01)87265-3

  日期：1993.1

  The chromium(0) mediated [6+2] cycloaddition reactions of a variety of cyclic trienes with substituted alkenes is detailed. The reactions can be effected either photochemically or thermally. Reactions promoted with catalytic quantities of chromium(0) are also described.

  详细介绍了各种环状三烯与取代烯烃的铬（0）介导的[6 + 2]环加成反应。反应可以光化学或热进行。还描述了催化量的铬（0）促进的反应。
• Reactions of azepine and diazepine derivatives with palladium acetate in benzene: a novel skeletal rearrangement of azepine derivatives
  作者：Katsuhiro Saito、Yoichi Horie、Kensuke Takahashi

  DOI：10.1016/0022-328x(89)88057-x

  日期：1989.3

  Reactions of azepine derivatives with palladium acetate in benzene give the bicyclo[4.1.0]-3-azahepta-4-ene derivatives, although one diazepine derivative underwent ring-opening. A cycloheptatriene derivative yielded a phenylated product.

  氮杂pine衍生物与乙酸钯在苯中的反应产生双环[4.1.0] -3-氮杂庚烷-4-烯衍生物，尽管一种二氮杂derivative衍生物经历开环。环庚三烯衍生物产生苯基化产物。
• 1,3-Dipolar Cycloadditions of N,a-Diphenylnitrone to the 4,5-Positions of 1H-Azepine and 1H-1,2-Diazepine Derivatives: Formation of endo- and exo-Type Cycloadducts and Computer-assisted Line Shape Simulation of the Nmr spectra of the Adducts
  作者：Katsuhiro Saito、Akihiro Yoshino、Kensuke Takahashi

  DOI：10.3987/com-90-5495

  日期：——

  Reaction of 1-carbomethoxy-1H-azepine with N, alpha-diphenylnitrone afforded two stereochemical isomers in almost the same ratio. The analysis of the nmr spectra of the cycloadducts were confirmed by good coincidence of the spectra to those obtained by computer assisted line shape simulation. The analogous result was obtained in the reaction using 1-carboethoxy-1H-1,2-diazepine. The reaction is considered to proceed through concerted [4+2]-type 1,3-dipolar cycloadditions of the nitrone to the 4,5-positions of the azepine or diazepine to give endo- and exo-type adducts because of the absence of stabilization effects by secondary orbital interactions in the transition states.