5-methoxythiophen-3-carboxaldehyde | 78395-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methoxythiophen-3-carboxaldehyde
• 英文别名: 5-Methoxy-3-formylthiophene；5-methoxy-3-thiophenecarboxaldehyde；5-methoxythiophene-2-carbaldehyde；5-methoxythiophene-3-carboxaldehyde；5-Methoxythiophene-3-carbaldehyde
• CAS: 78395-10-5
• 化学式: C₆H₆O₂S
• 分子量: 142.178
• InChiKey: PPIKDLGTJPOEBM-UHFFFAOYSA-N

物化性质

• 沸点：
  115-118 °C(Press: 13 Torr)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxythiophen-3-carboxaldehyde 在 盐酸 、 lithium aluminium tetrahydride 、 sodium methylate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.58h， 生成 2-phenyl-N-<2-(5-methoxythiophen-3-yl)ethyl>acetamide
  参考文献：
  名称：

  Synthesis and evaluation of 2-(5-methoxythiophen-3-yl)ethylamines as potential dopamine agonists

  摘要：

  The synthesis of 2-(5-methoxythiophen-3-yl)ethylamine and some derivatives bearing propyl and 2-phenylethyl substituents on the amino group has been described. The affinities for dopamine D-1 and D-2 receptors were evaluated by binding assays on rat striatum. None of the compounds show affinity for the D-1 receptor. In the D-2 binding assays the N-propyl-N-(2- phenylethyl) derivatives show affinity similar to that of the reference compound N-n-propyl-N-(2-phenylethyl)-2-(3-hydroxy- phenyl)ethylamine (1, RU 24213). In preliminary behavioral tests [2-(5-methoxythiophen-3-yl)ethyl]phenethylpropylamine behaves as a selective D-2 agonist.

  DOI：

  10.1016/0223-5234(94)90069-8
• 作为产物：
  描述：

  4-Iodo-2-methoxythiophene 以62%的产率得到
  参考文献：
  名称：

  GOLDFARB YA. L.; KALIK M. A.; ZAVYALOVA V. K., XIMIYA GETEROTSIKL. SOEDIN., 1981, HO 2, 182-188

  摘要：

  DOI：

文献信息

• Discovery of Dihydropyrrolo[1,2-<i>a</i>]pyrazin-3(4<i>H</i>)-one-Based Second-Generation GluN2C- and GluN2D-Selective Positive Allosteric Modulators (PAMs) of the <i>N</i>-Methyl-<scp>d</scp>-Aspartate (NMDA) Receptor
  作者：Matthew P. Epplin、Ayush Mohan、Lynnea D. Harris、Zongjian Zhu、Katie L. Strong、John Bacsa、Phuong Le、David S. Menaldino、Stephen F. Traynelis、Dennis C. Liotta

  DOI：10.1021/acs.jmedchem.9b01733

  日期：2020.7.23

  to increase glutamate potency 2-fold, increase the response to maximally effective concentration of agonist 4-fold, and the racemate is brain-penetrant. These compounds are useful second-generation in vitro tools and a promising step toward in vivo tools for the study of positive modulation of GluN2C- and GluN2D-containing NMDA receptors.

  所述Ñ甲基d天冬氨酸受体（NMDAR）为离子通道介导的是缓慢，钙2+谷氨酸能突触传递中的中枢神经系统（CNS）可透过的组件。已知NMDAR在基本的神经功能中起重要作用，其功能障碍与多种CNS疾病有关。在这里，我们报告发现具有二氢吡咯并[1,2 - a ]吡嗪-3（4 H）-一个核心的第二代GluN2C / D选择性NMDAR阳性变构调节剂（PAM）。原型R -（+）-EU-1180-453，与第一代原型CIQ相比，在双受体反应，亲脂性和水溶性方面所需浓度提高了log单位，并且cLogP降低了一个log单位。此外，发现R -（+）-EU-1180-453可将谷氨酸效能提高2倍，对激动剂的最大有效浓度的响应也可提高4倍，并且外消旋物具有大脑渗透性。这些化合物是有用的第二代体外工具，对于研究含GluN2C和含GluN2D的NMDA受体的正向调节的体内工具迈出了有希望的一步。
• PHENYL-OXAZOLYL DERIVATIVES, PREPARATION METHOD THEREOF, AND RELATED APPLICATION OF THE PHENYL-OXAZOLYL DERIVATIVES AS AN IMPDH INHIBITOR
  申请人：INSTITUTE OF MEDICINAL BIOTECHNOLOGY, CHINESE ACADEMY OF MEDICAL SCIENCES

  公开号：US20150031686A1

  公开（公告）日：2015-01-29

  Disclosed are phenyl-oxazolyl derivatives having a general formula (I), a preparation method thereof, and an application of the phenyl-oxazolyl derivatives as an inosine monophosphate dehydrogenase (IMPDH) inhibitor.

  揭示了具有一般式（I）的苯基-噁唑基衍生物，其制备方法以及将苯基-噁唑基衍生物作为肌醇单磷酸脱氢酶（IMPDH）抑制剂的应用。
• Synthesis and Antitumor Activity of Duocarmycin Derivatives: A-Ring Pyrrole Compounds Bearing 5-Membered Heteroarylacryloyl Groups.
  作者：Nobuyoshi AMISHIRO、Satoru NAGAMURA、Eiji KOBAYASHI、Akihiko OKAMOTO、Katsushige GOMI、Hiromitsu SAITO

  DOI：10.1248/cpb.47.1393

  日期：——

  A series of A-ring pyrrole compounds of duocarmycin bearing 5-membered heteroarylacryloyl groups (thienylacryloyl and pyrrolylacryloyl) and heteroarylcarbonyl groups were synthesized and evaluated for in vitro anticellular activity against HeLa S3 cells and in vivo antitumor activity against murine sarcoma 180 in mice. Most of the thienylacrylates displayed in vitro anticellular activity equivalent to 4'-methoxycinnamates. Among the 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of methoxy-thienylacrylates, compound 11b, having 4'-methoxy-2'-thienylacryloyl as segment-B (Seg-B), showed remarkably potent antitumor activity and low peripheral blood toxicity in vivo, which were equal to those of 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxycinnamates, compared with the A-ring pyrrole derivatives having the trimethoxyindole skeleton in Seg-B. On the other hand, the 2'-pyrrolylacrylates having a double bond as spacer showed 102- to 103-fold stronger anticellular activity than 2'-pyrrolecarboxylates (IC50<0.3nM, 72 h-exposure). The 8-O-acetate and 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 2'-pyrrolylacrylates exhibited an antitumor effect at a lower dose compared with the 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxycinnamate (1j). Moreover, it was expected that the antitumor activity would be increased by the strength of the extra hydrogen bond formed between the nitrogen of the pyrrole amido group and DNA, owing to the increase of the number of N-methyl-2'-pyrrolecarboxamide units. However, 2'-pyrrolylacrylates having three N-methyl-2'-pyrrolecarboxamide units showed nearly equal antitumor activity to 2'-pyrrolylacrylates having only one N-methyl-2'-pyrrolecarboxamide unit.

  合成了一系列带有 5 元杂芳基丙烯酰基（噻吩基丙烯酰基和吡咯基丙烯酰基）和杂芳基羰基的二氢霉素 A 环吡咯化合物，并评估了这些化合物对 HeLa S3 细胞的体外抗细胞活性和对小鼠 180 型鼠肉瘤的体内抗肿瘤活性。大多数噻吩丙烯酸酯的体外抗细胞活性与 4'-甲氧基肉桂酸酯相当。在甲氧基噻吩丙烯酸酯的 8-O-[（N-甲基哌嗪基）羰基]衍生物中，以 4'-甲氧基-2'-噻吩丙烯酰基为 B 段（Seg-B）的化合物 11b 显示出显著的抗肿瘤活性和较低的体内外周血毒性、与 Seg-B 中具有三甲氧基吲哚骨架的 A 环吡咯衍生物相比，4'-甲氧基肉桂酸盐的 8-O-[（N-甲基哌嗪基）羰基]衍生物具有相同的抗肿瘤活性和低外周血毒性。另一方面，以双键为间隔的 2'- 吡咯丙烯酸酯的抗细胞活性比 2'- 吡咯羧酸酯强 102-103 倍（IC50<0.3nM，72 小时暴露）。与 4'-methoxycinnamate 的 8-O-[(N-甲基哌嗪基)羰基]衍生物相比，2'-吡咯烷丙烯酸酯的 8-O-乙酸酯和 8-O-[(N-甲基哌嗪基)羰基]衍生物的抗肿瘤作用剂量较低（1j）。此外，由于 N-甲基-2'-吡咯甲酰胺单位数量的增加，吡咯氨基氮与 DNA 之间形成的额外氢键的强度预计会提高抗肿瘤活性。不过，具有三个 N-甲基-2'-吡咯甲酰胺单元的 2'-吡咯丙烯酸酯与只有一个 N-甲基-2'-吡咯甲酰胺单元的 2'-吡咯丙烯酸酯的抗肿瘤活性几乎相同。
• 一种正极补锂添加剂及其制备方法、补锂层、正极极片和锂离子电池
  申请人：江苏蓝固新能源科技有限公司

  公开号：CN117384189A

  公开（公告）日：2024-01-12

  本发明提供了一种正极补锂添加剂及其制备方法、补锂层、正极极片和锂离子电池。所述正极补锂添加剂其脱锂电位低，稳定性好，脱锂过程不会产生气体，且生成的有机部分溶于电解液，与电解液中HF反应，不仅能降低电解液酸度，还可以形成LiF的无机CEI膜成分，噻吩中间体在电极表面发生电化学聚合生成聚噻吩衍生物的有机CEI成分，使得CEI膜具有低阻抗高稳定性，抑制高电压下电解液与正极界面的副反应，降低电池内阻，且电解液中的噻吩类衍生物与锂离子具有较好的配位结合能力，有助于提高电解液的抗分解能力，进而提高锂离子电池的效率和循环性能。
• Synthesis and transformations of sulfides of the thiophene series. 33. Structures of the products of formylation of 2-methoxy-5-methylthiothiophene
  作者：Ya. L. Gol'dfarb、M. A. Kalik、V. K. Zav'yalova

  DOI：10.1007/bf00507241

  日期：1981.2