2-环丙甲基氨基-5-氯二苯甲酮 | 2897-00-9

• 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: 2-环丙甲基氨基-5-氯二苯甲酮
• 英文名称: 2-N-cyclopropmethylamino-5-chloro-benzophenone
• 英文别名: 5-chloro-2-cyclopropylmethylaminobenzophenone；2-Cyclopropylmethylamino-5-chlorbenzophenon；{5-Chloro-2-[(cyclopropylmethyl)amino]phenyl}(phenyl)methanone；[5-chloro-2-(cyclopropylmethylamino)phenyl]-phenylmethanone
• CAS: 2897-00-9
• 化学式: C₁₇H₁₆ClNO
• 分子量: 285.773
• InChiKey: WCRKZICZCPHVAB-UHFFFAOYSA-N

物化性质

• 熔点：
  79-80 °C
• 密度：
  1.252
• 保留指数：
  2349;2410;2370;2398;2385;2407

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922399090

反应信息

• 作为反应物：
  描述：

  2-环丙甲基氨基-5-氯二苯甲酮 生成 2-chloro-10-(cyclopropylmethyl)acridin-9-one
  参考文献：
  名称：

  DE, GIOVANNI N.;CHIAROTTI, M., J. CHROMATOGR.-BIOMED. APPL., 428,(1988) N 2, 321-329

  摘要：

  DOI：
• 作为产物：
  描述：

  普拉西 生成 2-环丙甲基氨基-5-氯二苯甲酮
  参考文献：
  名称：

  DE, GIOVANNI N.;CHIAROTTI, M., J. CHROMATOGR.-BIOMED. APPL., 428,(1988) N 2, 321-329

  摘要：

  DOI：

文献信息

• Synthetic studies on quinazoline derivatives. II. The reactions of 2-trichloro- and 2-trifluoroacetamidobenzophenones with primary amines.
  作者：MICHIHIRO YAMAMOTO、HISAO YAMAMOTO

  DOI：10.1248/cpb.29.2135

  日期：——

  The reaction of 5-chloro-2-trichloroacetamidobenzophenone (2a) with several primary alkylamines in DMSO gave high yields of 3-substituted 6-chloro-3, 4-dihydro-4-phenyl-4-trichloromethyl-2(1H)-quinazolinones 6, which were found to be formed by base-catalyzed and/or thermal cyclization and simultaneous rearrangement of the isomeric 5-chloro-2-trichloroacetamidobenzophenone alkylimines 5. Both compounds 5 and 6 were obtained when the reaction was effected in benzene. Treatment of the compound 2a with bulky amines such as isopropylamine and cyclohexylamine gave, under similar conditions, the corresponding benzophenone imines 5d and 5e exclusively, and these could be transformed into the quinazolinones 6d and 6e, respectively, on heating in pyridine or HMPT. The reaction of N-substituted trichloroacetamidobenzophenones 2m and 3n with N-(2-aminoethyl) morpholine as well as ammonia in DMSO yielded the 1-alkylaminobenzophenone imines 4m-o, which on treatment with trichloroacetyl chloride were readily cyclized to give the corresponding 1-substituted 4-trichloromethylquinazolinones 6m-o. The trichloromethyl group of the 1-unsubstituted quinazolinones 6 was easily displaced by a nucleophile such as hydride, alkoxide or hydroxide under base catalysis to give the 3, 4-dihydro-2 (1H)-quinazolinone derivative 9, 10 or 11 almost quantitatively, whereas the 1, 3-disubstituted quinazolinone 6o was not affected. The sodium borohydride reduction of the methylimine 5a at room temperature mainly afforded the trichloroacetamidobenzhydrylamine 8a, which underwent thermal cyclization to the quinazolinone 9a via split of chloroform. In contrast, the reaction of 5-chloro-2-trifluoroacetamidobenzophenone (2p) with some primary alkylamines in DMSO produced the trifluoroacetamidobenzophenone alkylimines 5p-r, which on treatment with sodium borohydride could be converted only to 3-substituted 6-chloro-3, 4-dihydro-4-phenyl-2-trifluoromethylquinazolines 15. These procedures were successfully utilized in syntheses of the imidazo [1, 2-c] quinazolinone 16, oxazolo [3, 2-c] quinazolinones 17t and 17v, and 1, 3-oxazino [3, 2-c] quinazolinone 17u.

  5-氯-2-三氯乙酰氨基苯并酮(2a)与几种初级烷基胺在DMSO中反应，得到了高产率的3取代的6-氯-3, 4-二氢-4-苯基-4-三氯甲基-2(1H)-喹唑啉酮 6，这些化合物被发现是通过碱催化和/或热环化以及异构体5-氯-2-三氯乙酰氨基苯并酮烷基亚胺的同时重排形成的。两种化合物5和6在苯中反应时均可获得。用体积较大的胺如异丙胺和环己胺处理化合物2a，在类似条件下，得到了相应的苯并酮亚胺5d和5e，经过加热于吡啶或HMPT中，这些亚胺分别可以转化为喹唑啉酮6d和6e。N-取代的三氯乙酰氨基苯并酮2m和3n与N-(2-氨基乙基)吗啉和氨在DMSO中反应，生成了1-烷基氨基苯并酮亚胺4m-o，经过与三氯乙酸酰氯的处理后，这些亚胺可以被迅速环化，得到相应的1-取代的4-三氯甲基喹唑啉酮6m-o。1-未取代的喹唑啉酮6中的三氯甲基基团在碱催化下可以很容易地被氢负离子、烷氧基或氢氧根等亲核试剂取代，几乎定量地产生3, 4-二氢-2(1H)-喹唑啉酮衍生物9、10或11，而1, 3-二取代的喹唑啉酮6o则没有受到影响。在室温下，甲基亚胺5a的钠硼氢化物还原主要产生了三氯乙酰氨基苯基胺8a，该物质经过热环化通过氯仿分解生成喹唑啉酮9a。相比之下，5-氯-2-三氟乙酰氨基苯并酮(2p)与一些初级烷基胺在DMSO中反应，生成了三氟乙酰氨基苯并酮烷基亚胺5p-r，经过与钠硼氢化物的处理后，仅能转化为3取代的6-氯-3, 4-二氢-4-苯基-2-三氟甲基喹唑啉15。这些程序成功应用于合成咪唑[1, 2-c]喹唑啉酮16、噁唑[3, 2-c]喹唑啉酮17t和17v，以及1, 3-噁唑啉[3, 2-c]喹唑啉酮17u。
• Cyclometallated derivatives of palladium(II) with 1,4-benzodiazepin-2-ones. Crystal structure of (L-H)Pd(PPh3)Cl·CHCl3 (L = Prazepam: 7-chloro-1-cyclopropylmethyl-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one). Synthesis of isoindolo[2,1-d][1,4]benzodiazepine derivatives by reaction of [(L-H)PdCl]2 species with carbon monoxide
  作者：Maria Agostina Cinellu、Serafino Gladiali、Giovanni Minghetti、Sergio Stoccoro、Francesco Demartin

  DOI：10.1016/0022-328x(91)86234-h

  日期：1991.1

  The dimeric cyclometallated derivatives of palladium(II) [(L-H)PdCl]2, 3 (L = 1, Diazepam: 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one) and 4 (L = 2, Prazepam: 7-chloro-1-cyclopropylmethyl-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one) react with triphenylphosphine to give the complexes (L-H)Pd(PPh3)Cl, 5(L = Diazepam) and 6 (L = Prazepam). The crystal structure of 6 was determined

  钯的二聚环金属化衍生物（II）[（大号-H）的PdCl] 2，3（大号= 1，地西泮：7-氯-1,3-二氢-1-甲基-5-苯基-2- ħ -1， 4-苯并二氮杂-2-酮）和4（L = 2，普拉西p：7-氯-1-环丙基甲基-1,3-二氢-5-苯基-2 H -1,4-苯并二氮杂-2-酮）与三苯基膦得到配合物（L -H）Pd（PPh 3）Cl，5（L =地西p）和6（L =地西Pra）。6的晶体结构通过X射线晶体学测定。钯原子呈正方形平面排列。去质子化的配体通过4-氮和5-苯基取代基的邻碳原子与金属结合。磷和氯原子是反式分别与氮和碳原子，：PdN= 2.085（2），PdP= 2.263（1），PdCl= 2.377（1），PdC= 2.009 （3）Å。
• Schutz; Fitz, Arzneimittel-Forschung/Drug Research, 1982, vol. 32, # 3, p. 177 - 183
  作者：Schutz、Fitz

  DOI：——

  日期：——
• YAMAMOTO, MICHIHIRO;YAMAMOTO, HISAO, CHEM. AND PHARM. BULL., 1981, 29, N 8, 2135-2156
  作者：YAMAMOTO, MICHIHIRO、YAMAMOTO, HISAO

  DOI：——

  日期：——
• YAMAMOTO M.; INABA S.; YAMAMOTO H., CHEM. AND PHARM. BULL., 1978, 26, NO 6, 1633-1651
  作者：YAMAMOTO M.、 INABA S.、 YAMAMOTO H.

  DOI：——

  日期：——

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