2-氧代-4-戊烯酸 | 20406-62-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 2-氧代-4-戊烯酸
• 英文名称: 2-oxopent-4-enoic acid
• 英文别名: 2-oxo-4-pentenoic acid
• CAS: 20406-62-6
• 化学式: C₅H₆O₃
• mdl: MFCD19228524
• 分子量: 114.101
• InChiKey: NOXRYJAWRSNUJD-UHFFFAOYSA-N

物化性质

• 沸点：
  180.0±19.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  2-氧代-4-戊烯酸 在 platinum(IV) oxide 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 L-正缬氨酸
  参考文献：
  名称：

  Moriguchi, Mitsuaki; Hoshino, Seiichi; Hatanaka, Shin-Ichi, Agricultural and Biological Chemistry, 1987, vol. 51, # 12, p. 3295 - 3300

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基-2-氧代戊酸 在 4-hydroxy 2- oxovalerate dehydratase 作用下， 生成 2-氧代-4-戊烯酸
  参考文献：
  名称：

  [EN] MICROORGANISMS FOR PRODUCING 4C-5C COMPOUNDS WITH UNSATURATION AND METHODS RELATED THERETO
  [FR] MICRO-ORGANISMES POUR LA PRODUCTION DE COMPOSÉS EN 4C-5 C AVEC UNE INSATURATION ET PROCÉDÉS ASSOCIÉS

  摘要：

  该发明提供了一种具有丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇途径的非自然微生物生物体。该微生物生物体含有至少一个编码途径中酶的外源核酸。该发明还提供了一种生产丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇的方法。该方法可以包括培养一种生产丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇的微生物生物体，其中该微生物生物体表达至少一个编码途径酶的外源核酸，且在足够的量下，在适当的条件和足够的时间内产生丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇。

  公开号：

  WO2016004334A1

文献信息

• Metabolism of 4-Amino-3-hydroxybenzoic Acid by<i>Bordetella</i>sp. Strain 10d: A Different Modified<i>Meta</i>-Cleavage Pathway for 2-Aminophenols
  作者：Chika ORII、Shinji TAKENAKA、Shuichiro MURAKAMI、Kenji AOKI

  DOI：10.1271/bbb.60264

  日期：2006.11.23

  Bordetella sp. strain 10d metabolizes 4-amino-3-hydroxybenzoic acid via 2-hydroxymuconic 6-semialdehyde. Cell extracts from 4-amino-3-hydroxybenzoate-grown cells showed high NAD+-dependent 2-hydroxymuconic 6-semialdehyde dehydrogenase, 4-oxalocrotonate tautomerase, 4-oxalocrotonate decarboxylase, and 2-oxopent-4-enoate hydratase activities, but no 2-hydroxymuconic 6-semialdehyde hydrolase activity. These enzymes involved in 4-amino-3-hydroxybenzoate metabolism were purified and characterized. When 2-hydroxymuconic 6-semialdehyde was used as substrate in a reaction mixture containing NAD+ and cell extracts from 4-amino-3-hydroxybenzoate-grown cells, 4-oxalocrotonic acid, 2-oxopent-4-enoic acid, and 4-hydroxy-2-oxovaleric acid were identified as intermediates, and pyruvic acid was identified as the final product. A complete pathway for the metabolism of 4-amino-3-hydroxybenzoic acid in strain 10d is proposed. Strain 10d metabolized 2-hydroxymuconic 6-semialdehyde derived from 4-amino-3-hydroxybenzoic acid via a dehydrogenative route, not via a hydrolytic route. This proposed metabolic pathway differs considerably from the modified meta-cleavage pathway of 2-aminophenol and those previously reported for methyl- and chloro-derivatives.

  Bordetella sp. 10d株通过2-羟基穆康酸6-半醛代谢4-氨基-3-羟基苯甲酸。来自于培养于4-氨基-3-羟基苯甲酸的细胞的细胞提取物显示出高水平的NAD+-依赖性2-羟基穆康酸6-半醛脱氢酶、4-草酰克罗通酸互变异构酶、4-草酰克罗通酸脱羧酶和2-氧戊-4-烯酸水合酶活性，但没有检测到2-羟基穆康酸6-半醛水解酶活性。这些参与4-氨基-3-羟基苯甲酸代谢的酶被纯化并进行了特征分析。当在含有NAD+和来自于4-氨基-3-羟基苯甲酸的细胞提取物的反应混合物中使用2-羟基穆康酸6-半醛作为底物时，4-草酰克罗通酸、2-氧戊-4-烯酸和4-羟基-2-氧戊酸被鉴定为中间产物，而丙酮酸被鉴定为最终产物。提出了10d株对4-氨基-3-羟基苯甲酸的完整代谢途径。10d株通过脱氢途径代谢由4-氨基-3-羟基苯甲酸衍生的2-羟基穆康酸6-半醛，而不是通过水解途径。这种提议的代谢途径与2-氨基酚的改良元断裂途径以及之前报道的甲基和氯衍生物的途径有显著不同。
• Synthesis, Molecular Engineering, and Photophysical Properties of Fluorescent Thieno[3,2-<i>b</i>]pyridine-5(4<i>H</i>)-ones
  作者：Dan-Bi Sung、Bohyun Mun、Sol Park、Hyi-Seung Lee、Jihoon Lee、Yeon-Ju Lee、Hee Jae Shin、Jong Seok Lee

  DOI：10.1021/acs.joc.8b01924

  日期：2019.1.4

  fluorescent thieno[3,2-b]pyridine-5(4H)-one derivatives and their photophysical properties. These fluorophores are prepared by a series of reactions employing the Suzuki–Miyaura cross-coupling reaction and a regioselective aza-[3 + 3] cycloaddition of 3-aminothiophenes with α,β-unsaturated carboxylic acids. Our findings revealed that the photophysical properties are chemically tunable by an appropriate

  我们描述了一套荧光thieno [3,2 - b ]吡啶-5（4 H）-衍生物及其光物理性质的合成方法。这些荧光团是通过一系列使用铃木-宫浦交叉偶联反应和3-氨基噻吩与α，β-不饱和羧酸的区域选择性氮杂-[3 + 3]环加成反应制备的。我们的研究结果表明，光物理性质是由官能团上的噻吩并[3,2-一个合适的选择化学可调b ]吡啶5（4 ħ） -酮支架。
• As-triazinobenzodiazepin-1-ones
  申请人：The Upjohn Company

  公开号：US04017492A1

  公开（公告）日：1977-04-12

  Compounds of the formula IV: ##STR1## wherein R.sub.o is hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, --C.sub.n H.sub.2n OR in which n is an integer of 1 to 3, inclusive, and R is hydrogen or methyl, ##STR2## in which n is defined as above, and R.sub.6 and R.sub.7 are hydrogen or alkyl as defined above, or together ##STR3## is pyrrolidino, piperidino, morpholino or ##STR4## in which R.sub.8 is methyl, ethyl, or 2-hydroxyethyl, ##STR5## in which m is an integer of 0 to 3, inclusive, and R.sub.9 is hydrogen, lower alkyl of from 1 to 3 carbon atoms, inclusive, wherein R.sub.1 is hydrogen or methyl; wherein R.sub.2 is phenyl, o-chlorophenyl, o-fluorophenyl, 2,6-difluorophenyl, or 2-pyridyl; and wherein R.sub.3 is hydrogen, fluoro, chloro, bromo, trifluoromethyl, or nitro. The compounds of formula IV and the pharmacologically acceptable acid addition salts thereof have sedative, tranquilizing, anticonvulsive and muscle-relaxant activity and can thus be used to produce sedation and tranquilization in mammals, including man, and birds.

  公式IV的化合物：## STR1 ## 其中R.sub.o是氢，1至3个碳原子的烷基，包括，-C.sub.n H.sub.2n或其中n为1至3的整数，包括，而R为氢或甲基，## STR2 ## 其中n如上所述，R.sub.6和R.sub.7为氢或如上定义的烷基，或一起## STR3 ## 是吡咯烷基，哌啶基，吗啉基或## STR4 ## 其中R.sub.8为甲基，乙基或2-羟乙基，## STR5 ## 其中m是0至3的整数，包括，而R.sub.9是氢，1至3个碳原子的低烷基，其中R.sub.1为氢或甲基;其中R.sub.2为苯基，o-氯苯基，o-氟苯基，2,6-二氟苯基或2-吡啶基;而R.sub.3为氢，氟，氯，溴，三氟甲基或硝基。公式IV的化合物及其药理学上可接受的酸盐具有镇静，安定，抗惊厥和肌肉松弛活性，因此可用于在哺乳动物，包括人类和鸟类中产生镇静和安定作用。
• Pollard, John R.; Henderson, Ian M. J.; Bugg, Timothy D. H., Chemical Communications, 1997, # 19, p. 1885 - 1886
  作者：Pollard, John R.、Henderson, Ian M. J.、Bugg, Timothy D. H.

  DOI：——

  日期：——
• The Contribution of the Substrate's Carboxylate Group to the Mechanism of 4-Oxalocrotonate Tautomerase
  作者：Huiling Lian、Robert M. Czerwinski、Thanuja M. Stanley、William H. Johnson、Robert J. Watson、Christian P. Whitman

  DOI：10.1006/bioo.1998.1095

  日期：1998.10

  4-Oxalocrotonate tautomerase (4-OT) converts 2-oxo-4E-hexenedioate (1) to 2-oxo-3E-hexenedioate (3) through the dienol intermediate, 2-hydroxy-2,4-hexadiene-1,6-dioate (2). Previous studies established that the isomerization of 1 to 3 is primarily a suprafacial process. It was also suggested that the 6-carboxylate group of the substrate maintains the regio- and stereochemical fidelity of the reaction by anchoring the substrate at the active site. A subsequent study suggested an additional role for the 6-carboxylate group in the mechanism: the enzyme may utilize the binding energy of the carboxylate group to facilitate catalysis. In order to explore the role of the carboxylate group in the mechanism further, the nonenzymatic rate constants for mono- and dicarboxylated substrates were measured and compared to the rates obtained for the corresponding enzymatic reactions. The results show that the missing carboxylate group has a profound effect on enzymatic catalysis as evidenced by the significant decreases (a 10(4)- and a 10(5)-fold reduction) in the values of k(cat)/K-m observed for the two monocarboxylated substrates. A comparison of the nonenzymatic rate constants indicates that the reduced k(cat)/K-m values cannot be explained on the basis of the chemical reactivities. The stereochemical course of the 4-OT-catalyzed reaction was also determined using 2-hydroxy-2,4Z-heptadiene-1,7-dioate. The stereochemical analysis reveals that the presence of the carboxylate group improves the stereoselectivity of the enzyme-catalyzed ketonization of 2-hydroxy-2,4Z-heptadiene-1,7-dioate to 2-oxo-[3-H-2]-4Z-heptene-1,7-dioate in (H2O)-H-2-a result that is consistent with its previously assigned role. These findings provide further evidence that the substrate's carboxylate group contributes to the mechanism of the enzyme in two ways: it anchors the substrate at the active site and it facilitates catalysis by destabilizing the substrate or by stabilizing the transition state. (C) 1998 Academic Press.