2-acetylamino-2-ethoxycarbonyl-3-<2(1H)-quinolinon-4-yl>propionate | 90097-61-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-acetylamino-2-ethoxycarbonyl-3-<2(1H)-quinolinon-4-yl>propionate
• 英文别名: 4-(2-bromoethyl)-2(1H)-quinolone；4-(2'-bromoethyl)quinolone；4-(2-bromoethyl)-2(1H)-quinolinone；4-(2-Bromoethyl)quinolin-2(1H)-one；4-(2-bromoethyl)-1H-quinolin-2-one
• CAS: 90097-61-3
• 化学式: C₁₁H₁₀BrNO
• 分子量: 252.11
• InChiKey: VIPBATDIPNJLFM-UHFFFAOYSA-N

物化性质

• 沸点：
  411.6±45.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-acetylamino-2-ethoxycarbonyl-3-<2(1H)-quinolinon-4-yl>propionate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-benzyl-2-ethyl-N-[2-(2-oxo-1,2-dihydro-4-quinolyl)ethyl]acrylamide
  参考文献：
  名称：

  Photochemistry of 4-(2‘-Aminoethyl)quinolones:  Enantioselective Synthesis of Tetracyclic Tetrahydro-1aH-pyrido[4‘,3‘:2,3]- cyclobuta[1,2-c] Quinoline-2,11(3H,8H)-diones by Intra- and Intermolecular [2 + 2]-Photocycloaddition Reactions in Solution

  摘要：

  Enantioselective [2 + 2]-photocycloaddition reactions on 4-(2'-aminoethyl) quinolones in solution were studied using the enantiomerically pure complexing agent 1 as source of chirality. The intermolecular reactions of fully N-protected substrates 5a-5c with different 2-alkyl-substituted acrylates 12-15 represent the first systematic study on the diastereoselectivity of their intermolecular [2 + 2]-photocycloadditions to unsymmetrically 1,1-disubstituted olefins (75-91% yield, d.r. = 58/42-95/5). N-Benzylic-protected photoproducts exo-16a/b-19a/b could easily be converted into lactams 20a/b-23a/b by a sequence of Boc deprotection and thermal lactamization (74-98% yield). Identical products 20a-22a were directly accessible by the intramolecular [ 2 + 2]-photocycloaddition of acrylic acid amides 2-4 (41-61% yield). The suitability of both pathways for an enantioselective reaction variant was proven (70-92% ee). Thus, tetracyclic lactams possessing the carbon framework C were obtained with good yields and enantio-selectivities of up to 92% ee in intramolecular reactions. Comparative investigation of both routes showed that quinolone dimerization was the single most decisive factor preventing a complete chirality transfer. Functional group manipulations were successfully conducted with the primary photoproduct exo-17a. Finally, a new and unexpected type of benzylic hydrogen abstraction-radical cyclization reaction was discovered for substrate 5a, which explains the photochemical instability of substrates 2-5 under short wavelength irradiation (lambda = 300 nm).

  DOI：

  10.1021/jo0606608
• 作为产物：
  描述：

  2-羟基-4-甲基喹啉 在 lithium aluminium tetrahydride 、 正丁基锂 、 氯化亚砜 、 氢溴酸 作用下， 生成 2-acetylamino-2-ethoxycarbonyl-3-<2(1H)-quinolinon-4-yl>propionate
  参考文献：
  名称：

  Photochemistry of 4-(2‘-Aminoethyl)quinolones:  Enantioselective Synthesis of Tetracyclic Tetrahydro-1aH-pyrido[4‘,3‘:2,3]- cyclobuta[1,2-c] Quinoline-2,11(3H,8H)-diones by Intra- and Intermolecular [2 + 2]-Photocycloaddition Reactions in Solution

  摘要：

  Enantioselective [2 + 2]-photocycloaddition reactions on 4-(2'-aminoethyl) quinolones in solution were studied using the enantiomerically pure complexing agent 1 as source of chirality. The intermolecular reactions of fully N-protected substrates 5a-5c with different 2-alkyl-substituted acrylates 12-15 represent the first systematic study on the diastereoselectivity of their intermolecular [2 + 2]-photocycloadditions to unsymmetrically 1,1-disubstituted olefins (75-91% yield, d.r. = 58/42-95/5). N-Benzylic-protected photoproducts exo-16a/b-19a/b could easily be converted into lactams 20a/b-23a/b by a sequence of Boc deprotection and thermal lactamization (74-98% yield). Identical products 20a-22a were directly accessible by the intramolecular [ 2 + 2]-photocycloaddition of acrylic acid amides 2-4 (41-61% yield). The suitability of both pathways for an enantioselective reaction variant was proven (70-92% ee). Thus, tetracyclic lactams possessing the carbon framework C were obtained with good yields and enantio-selectivities of up to 92% ee in intramolecular reactions. Comparative investigation of both routes showed that quinolone dimerization was the single most decisive factor preventing a complete chirality transfer. Functional group manipulations were successfully conducted with the primary photoproduct exo-17a. Finally, a new and unexpected type of benzylic hydrogen abstraction-radical cyclization reaction was discovered for substrate 5a, which explains the photochemical instability of substrates 2-5 under short wavelength irradiation (lambda = 300 nm).

  DOI：

  10.1021/jo0606608

文献信息

• Studies on 2(1H)-quinolinone derivatives as gastric antiulcer active agents. 2-(4-Chlorobenzoylamino)-3-(2(1H)-quinolinon-4-yl)propionic acid and related compounds.
  作者：MINORU UCHIDA、FUJIO TABUSA、MAKOTO KOMATSU、SEIJI MORITA、TOSHIMI KANBE、KAZUYUKI NAKAGAWA

  DOI：10.1248/cpb.33.3775

  日期：——

  A series of N-acyl amino acid analogues of 2 (1H)-quinolinone was synthesized and tested for antiulcer activity against acetic acid-induced gastric ulcer in rats. These compounds were synthesized by the acylation of amino acid derivatives of 2 (1H)-quinolinone, which were obtained from the reaction of ω-bromoalkyl 2 (1H)-quinolinones and acetamidomalonate in the presence of sodium ethoxide, followed by hydrolysis with diluted hydrochloric acid. Among them, 2-(4-chlorobenzoylamino)-3-[2 (1H)-quinolinon-4-yl] propionic acid (VIIIf) was found to have the most potent activity. The structure-activity relationships are discussed.

  合成了一系列N-酰基氨基酸类似物的2 (1H)-喹啉酮，并测试了它们对醋酸诱导的大鼠胃溃疡的抗溃疡活性。这些化合物是通过酰化2 (1H)-喹啉酮的氨基酸衍生物合成的，这些衍生物是通过ω-溴烷基2 (1H)-喹啉酮和乙酰胺基丙二酸酯在乙醇钠存在下反应，然后与稀盐酸水解得到的。其中，2-(4-氯苯甲酰氨基)-3-[2 (1H)-喹啉酮-4-基]丙酸(VIIIf)显示出最强的活性。讨论了结构活性关系。
• Carbostyril derivatives and antiallergic agent
  申请人：Sawai Pharmaceutical Co., Ltd.

  公开号：US05457099A1

  公开（公告）日：1995-10-10

  1. A compound of the formula: ##STR1## wherein the symbol of a solid line with a broken line means a single bond or a double bond, R and R' are independently selected from the group consisting of hydrogen atom, halogen atom, lower alkyl, nitro, unsubstituted amino and substituted amino, A and B are independently selected from the group consisting of hydrogen atom, lower alkyl optionally substituted with a lower cycloalkyl, aryl optionally substituted with one or more halogen atoms and the group: -Y-R.sup.2 wherein Y is lower alkylene and R.sup.2 is the group: ##STR2## wherein m is integer of 1 to 3, n is 0 or 1, Z is >N-, >CH-- or >C=, R.sup.3 is diaryl (lower) alkyl optionally substituted with one or more halogen atoms or is condensed heterocyclic group optionally substituted with oxo, with the proviso that (a) at least one of A and B is the group -Y-R.sup.2 and (b) when A is hydrogen atom and B is the group -Y-R.sup.2, then Z is >CH-- or >C= if R.sup.3 is condensed heterocyclic group optionally substituted with oxo and n is O or a pharmaceutically acceptable salt thereof. The compounds of the above formula have antiallergic activity.

  该化合物的结构式如下：##STR1##其中实线和虚线表示单键或双键，R和R'分别选自氢原子、卤素原子、低烷基、硝基、未取代氨基和取代氨基的群体，A和B分别选自氢原子、可选择用低环烷基取代的低烷基、可选择用一个或多个卤素原子取代的芳基以及该群体：-Y-R.sup.2，其中Y为低烷基，R.sup.2为该群体：##STR2##其中m为1至3的整数，n为0或1，Z为>N-、>CH--或>C=，R.sup.3为可选择用一个或多个卤素原子取代的二芳基（低）烷基或是可选择用氧代取代的缩杂环基团，但须满足(a)至少一个A和B为该群体-Y-R.sup.2，以及(b)当A为氢原子且B为该群体-Y-R.sup.2时，若R.sup.3为可选择用氧代取代的缩杂环基团且n为0，则Z为>CH--或>C=或其药用盐。上述结构的化合物具有抗过敏活性。
• Stereoselective Intra- and Intermolecular [2+2] Photocycloaddition Reactions of 4-(2′-Aminoethyl)quinolones
  作者：Thorsten Bach、Sebastian Brandes、Philipp Selig

  DOI：10.1055/s-2004-834817

  日期：——

  The 4-(2'-aminoethyl)quinolones 6, 8 and 9 were prepared starting from 4-(2'-bromoethyl)quinolone (4) in two steps and overall yields of 56-93%. They underwent inter- and intramolecular [2+2] photocycloaddition reactions with an alkene to provide the cyclobutanes 1-3 in racemic form (61-89% yield). The photochemical reaction proceeded with very good chemo-, regio- and stereoselectivity. It was in one

  4-(2'-氨基乙基)喹诺酮6、8和9以4-(2'-溴乙基)喹诺酮(4)为原料，分两步制备，总产率为56-93%。他们与烯烃进行分子间和分子内 [2+2] 光环加成反应，以提供外消旋形式的环丁烷 1-3（产率 61-89%）。光化学反应以非常好的化学选择性、区域选择性和立体选择性进行。在一种情况下 (8b → 2b) 也进行了对映选择性 (93% ee)。
• UTIDA, MINORU;KOMATSU, MAKOTO;NAKAGAVA, KADZUYUKI
  作者：UTIDA, MINORU、KOMATSU, MAKOTO、NAKAGAVA, KADZUYUKI

  DOI：——

  日期：——
• UCHIDA, MINORU;TABUSA, FUJIO;KOMATSU, MAKOTO;MORITA, SEIJI;KANBE, TOSHIMI+, CHEM. AND PHARM. BULL., 1985, 33, N 9, 3775-3786
  作者：UCHIDA, MINORU、TABUSA, FUJIO、KOMATSU, MAKOTO、MORITA, SEIJI、KANBE, TOSHIMI+

  DOI：——

  日期：——