4-cyanomethyl-1-(2,4-dimethoxybenzyl)azetidine-2-one | 91922-01-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 4-cyanomethyl-1-(2,4-dimethoxybenzyl)azetidine-2-one
• 英文别名: 4-(cyanomethyl)-1-(2,4-dimethoxybenzyl)-2-azetidinone；2-[1-[(2,4-dimethoxyphenyl)methyl]-4-oxoazetidin-2-yl]acetonitrile
• CAS: 91922-01-9
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: YRJHCVIUIBPYBX-UHFFFAOYSA-N

物化性质

• 沸点：
  500.4±40.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-cyanomethyl-1-(2,4-dimethoxybenzyl)azetidine-2-one 在 硫化氢 作用下， 以 吡啶 、 三乙胺 为溶剂， 反应 48.0h， 以68%的产率得到(RS)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-2-ylthioacetamide
  参考文献：
  名称：

  Fetter, Jozsef; Lempert, Karoly; Kajtar-Peterdy, Maria, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1453 - 1458

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 1-(2,4-dimethoxybenzyl)-4-oxo-2-azetidine-carboxylate 在 吡啶 、 sodium tetrahydroborate 、 sodium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 64.5h， 生成 4-cyanomethyl-1-(2,4-dimethoxybenzyl)azetidine-2-one
  参考文献：
  名称：

  Simig; Fetter; Hornyak, Acta Chimica Hungarica, 1985, vol. 119, # 1, p. 17 - 32

  摘要：

  DOI：

文献信息

• Azetidinone acetic acid derivatives and process for the preparation
  申请人：Richter Gedeon Vegyeszeti Gyar RT

  公开号：US04587049A1

  公开（公告）日：1986-05-06

  The invention relates to compounds of the general formula (X) ##STR1## wherein R is as a removable protecting substituent of the amido group a phenyl group or a benzyl group substituted by one or more alkoxy group(s) having 1-4 carbon atoms and R.sup.1 stands for a hydrogen atom or an alkyl group having 1-4 carbon atoms and a process for the preparation thereof. The compounds of the general formula (X) can be prepared from the starting materials of the general formula (V), wherein R and R.sup.1 are as stated above and Z is an alkyl group having 1-4 carbon atoms. The compounds of the general formula (X) are useful pharmaceutical intermediates which can be used in the preparation of known antibiotics (e.g. Thienamycin and PS-5).

  该发明涉及一般式（X）的化合物 ##STR1## 其中R是氨基团的可去保护取代基，为苯基或苄基，其上取代有一个或多个含有1-4个碳原子的烷氧基，R.sup.1代表氢原子或含有1-4个碳原子的烷基，以及其制备方法。一般式（X）的化合物可从一般式（V）的起始原料制备而得，其中R和R.sup.1如上所述，Z是含有1-4个碳原子的烷基。一般式（X）的化合物是有用的药物中间体，可用于制备已知的抗生素（例如Thienamycin和PS-5）。
• Heterocyclic compounds containing an alkoxycarbonyl and a substituted
  申请人：Richter Gedeon Vegyeszeti Gyar Rt.

  公开号：US04435322A1

  公开（公告）日：1984-03-06

  The invention relates to new heterocyclic compound containing an alkoxycarbonyl and a substituted methyl group a process for the preparation of these and analogeous compound and pharmaceutical compositions containing them. More particularly, the invention concerns compounds of the general formula (IVa) ##STR1## wherein R' is hydrogen, 2-ethoxycarbonylethyl, aryl or a group suitable for a temporary protection of amides and Y' represents a group of the formula --COOZ or --CH.sub.2 M, in which Z is lower alkyl and M is hydroxyl, halogen, cyano or a group of the formula --O--SO.sub.2 R.sup.2, in which R.sup.2 is lower alkyl or aryl, with the proviso that if R' is phenyl, Y' cannot stand for the group --COOC.sub.2 H.sub.5. The invention further relates to a process for the preparation of compounds of the general formula (IV) ##STR2## in which R and Y are identical with R' and Y', respectively, except the proviso. According to a further aspect of the invention there are provided pharmaceutical compositions, first of all with antihypoxic activity, comprising compounds of the general formula (IVa) as active ingredient.

  该发明涉及一种新的含有烷氧羰基和取代甲基基团的杂环化合物，以及制备这些类似化合物和制药组合物的方法。更具体地，该发明涉及具有一般式（IVa）的化合物，其中R'是氢、2-乙氧羰基乙基、芳基或适用于酰胺的暂时保护基团，Y'表示具有以下结构的基团--COOZ或--CH.sub.2 M，其中Z是较低的烷基，M是羟基、卤素、氰基或具有以下结构的基团--O--SO.sub.2 R.sup.2，其中R.sup.2是较低的烷基或芳基，但如果R'为苯基，则Y'不能表示基团--COOC.sub.2 H.sub.5。该发明还涉及一种制备一般式（IV）化合物的方法，其中R和Y与R'和Y'相同，除了上述规定外。根据该发明的另一个方面，提供了首先具有抗缺氧活性的药物组合物，其包括作为活性成分的一般式（IVa）化合物。
• Simple and condensed β-lactams. Part 14. Anomalous behaviour of 1-(4-methoxyphenyl)-4-(tetrazol-5-ylmethyl)azetidin-2-one towards cerium(<scp>IV</scp>) ammonium nitrate
  作者：József Fetter、Ernő Keskeny、Tibor Czuppon、Károly Lempert、Mária Kajtár-peredy、József Tamás

  DOI：10.1039/p19920003061

  日期：——

  Treatment of 1-(4-methoxyphenyl)azetidin-2-one 7 with cerium(IV) ammonium nitrate (CAN) fails to yield the N-deprotected product 6. Depending on the mode of work-up, N-substituted products 8-13 are obtained instead. The formation of these products may be rationalized by assuming interaction of the nucleophilic tetrazole and electrophilic quinone imine moieties of intermediate 21 to afford, after deprotonation, the spirocyclic quinone aminal 25. The latter, in contrast to quinone imine derivatives of type 3, is stable to hydrolysis under the conditions applied but reacts readily both with added sodium chloride and bromide as well as with reducing agents (NaHSO3, I-).
• BARTANE, SZALAI;ZAUER, KAROLY;LEMPERT, KAROLY;HARSANYI, KALMAN;DOLLESCHAL+
  作者：BARTANE, SZALAI、ZAUER, KAROLY、LEMPERT, KAROLY、HARSANYI, KALMAN、DOLLESCHAL+

  DOI：——

  日期：——
• US4435322A
  申请人：——

  公开号：US4435322A

  公开（公告）日：1984-03-06