6-Methyl-3-(phenylmethyl)-3,6-diazabicyclo<3.1.0>hexane-2,4-dione | 120566-61-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-Methyl-3-(phenylmethyl)-3,6-diazabicyclo<3.1.0>hexane-2,4-dione
• 英文别名: 3-Benzyl-6-methyl-3,6-diazabicyclo[3.1.0]hexane-2,4-dione
• CAS: 120566-61-2
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: GTVYIIAUVWEVAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Methyl-3-(phenylmethyl)-3,6-diazabicyclo<3.1.0>hexane-2,4-dione 在 titanium(IV) isopropylate 作用下， 以 1,4-二氧六环 为溶剂， 反应 40.0h， 生成 (1R-exo)-8-Methyl-2,4-dioxo-3-(phenylmethyl)-3,8-diazabicyclo[3.2.1]octane-6-carboxylic acid ethyl ester
  参考文献：
  名称：

  Development of an asymmetric approach to the 3,8-diazabicyclo[3.2.1]octane moiety of quinocarcin via intramolecular 1,3-dipolar cycloadditions of photochemically generated azomethine ylides

  摘要：

  Exploratory work culminating in an enantioselective approach to the DNA-reactive alkaloid quinocarcin (1) is detailed. The key step involves auxiliary-controlled dipolar cycloaddition between photochemically generated azomethine ylides such as 11 and Oppolzer's chiral acryloyl sultam (-)-32 to assemble the 6-exo-substituted 3,8-diazabicyclo[3.2.1]octane core of 1. The synthetic sequence begins with condensation of the benzylamines 3 and maleic anhydride to give the N-alkylated maleimides 6. Triazoline formation (MeN3) followed by photolytic (lambda > 3000 angstrom) extrusion of nitrogen leads to the corresponding aziridines 10. Upon irradiation at 2537 angstrom, these aziridines undergo electrocyclic ring-opening to give azomethine ylides 11, which can be trapped with (-)-32 to give the 6-exo-substituted cycloadduct 33 (diastereoselectivity, ds > 25:1). These results stand in sharp contrast to cycloadditions of 11 with (achiral and chiral) acrylate ester dipolarophiles as well as acrylonitrile, which proceed with no appreciable facial selectivity. The expected re-face selectivity of (-)-32 was confirmed in one case by X-ray crystallographic analysis of endo-adduct 35a. Removal (and recovery) of the chiral sultam auxiliary can be effected by titanium (IV)-mediated alcoholysis to give ester derivatives of the cycloadducts.

  DOI：

  10.1021/jo00020a035
• 作为产物：
  描述：

  N-苯基马来酸 以 1,4-二氧六环 、 甲苯 为溶剂， 生成 6-Methyl-3-(phenylmethyl)-3,6-diazabicyclo<3.1.0>hexane-2,4-dione
  参考文献：
  名称：

  一种通过光化学生成的偶氮甲碱碘化物的1,3-偶极环加成反应制得萘啶霉素和喹诺霉素的3,8-二氮杂双环[3.2.1]辛烷部分的方法。

  摘要：

  提出了一种有吸引力的策略，用于构建目标1和2的3,8-二氮杂双环[3.2.1]辛烷部分，涉及光化学生成的甲亚胺基团的1,3-偶极环加成。

  DOI：

  10.1016/0040-4039(88)85283-3

文献信息

• An approach to the 3,8-diazabicyclo[3.2.1]octane moiety of naphthyridinomycin and quinocarcin via 1,3-dipolar cycloaddition of photochemically generated azomethine ylides.
  作者：Philip Garner、K. Sunitha、T. Shanthilal

  DOI：10.1016/0040-4039(88)85283-3

  日期：1988.1

  An attractive strategy for construction of the 3,8-diazabicyclo[3.2.1]octane moiety of targets 1 and 2 involving the 1,3-dipolar cycloaddition of photochemically generated azomethine ylides is presented.

  提出了一种有吸引力的策略，用于构建目标1和2的3,8-二氮杂双环[3.2.1]辛烷部分，涉及光化学生成的甲亚胺基团的1,3-偶极环加成。
• Stereoselective 1,3-dipolar cycloadditions of photochemically generated azomethine ylides to Oppolzer's chiral acryloyl sultam. An asymmetric approach to quinocarcin
  作者：Philip Garner、Wen Bin Ho

  DOI：10.1021/jo00300a004

  日期：1990.6
• GARNER, PHILIP;SUNITHA, K.;SHANTHILAL, T., TETERAHEDRON LETT., 29,(1988) N 29, C. 3525-3528
  作者：GARNER, PHILIP、SUNITHA, K.、SHANTHILAL, T.

  DOI：——

  日期：——
• NOVEL QUINOLONE COMPOUNDS AND PROCESSES FOR PREPARATION THEREOF
  申请人：HANMI PHARMACEUTICAL CO.,LTD.

  公开号：EP0571400A1

  公开（公告）日：1993-12-01
• [EN] NOVEL QUINOLONE COMPOUNDS AND PROCESSES FOR PREPARATION THEREOF
  申请人：HANMI PHARMACEUTICAL CO., LTD.

  公开号：WO1992012155A1

  公开（公告）日：1992-07-23

  (EN) This invention relates to the novel quinolone compound of formula (I) having excellent antimicrobial activity both against gram positive and negative bacteria, its pharmaceutically acceptable salt, and the process for preparation thereof; wherein R1 is hydrogen or protective group, R2 is hydrogen, amino, alkylamino from one to four carbon atoms, hydroxy, alkoxy from one to four carbon atoms, mercapto, alkylthio from one to four carbon atoms, or halogen, R3 is alkyl from one to four carbon atoms, alkenyl from two to four carbon atoms, cycloalkyl from three to six carbon atoms, haloalkyl, hydroxyalkyl from two to four carbon atoms, methoxy, amino, alkylamino from one to two carbon atoms, dimethylamino, or optionally substituted phenyl with more than one of halogen atoms or alkyl from one to three carbon atoms, Z is an amine of formula (II), (wherein R4 is hydrogen or alkyl from one to four carbon atoms, R5 and R7 are, same or different, hydrogen or alkyl from one to two carbon atoms), X is N or C-R6 (wherein R6 is hydrogen, hydroxy, methyl, cyano, nitro, methoxy, halogen, or can form a bridge of formula (a), (b), (c) or (d) with R3.(FR) Nouveau composé de quinoléine répondant à la formule (I) et présentant une excellente activité antimicrobienne à la fois contre les bactéries Gram positif et contre les bactéries Gram négatif; son sel pharmaceutiquement acceptable; et son procédé de préparation. Dans ladite formule (I), R1 représente hydrogène ou un groupe protecteur; R2 représente hydrogène, amino, alkylamino C1-4, hydroxy, alcoxy C1-4, mercapto, alkylthio C1-4 ou halogène; R3 représente alkyle C1-4, alcényle C2-4, cycloalkyle C3-6, haloalkyle, hydroxyalkyle C2-4, méthoxy, amino, alkylamino C1-2, diméthylamino, ou phényle éventuellement substitué par au moins un atome d'halogène ou par alkyle C1-3; Z représente une amine répondant à la formule (II), dans laquelle R4 représente hydrogène ou alkyle C1-4 et R5 et R7 sont identiques ou différents et représentent hydrogène ou alkyle C1-2; et X représente N ou C-R6 où R6 représente hydrogène, hydroxy, méthyle, cyano, nitro, méthoxy ou halogène, ou forme, conjointement avec R3, un pont répondant à l'une des formules (a), (b), (c) ou (d).