双(3-甲基-2-噻吩基)甲酮 | 30717-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 双(3-甲基-2-噻吩基)甲酮
• 英文名称: bis(3-methylthien-2-yl)ketone
• 英文别名: Bis(3-methyl-2-thienyl)methanone；bis(3-methylthiophen-2-yl)methanone
• CAS: 30717-55-6
• 化学式: C₁₁H₁₀OS₂
• 分子量: 222.332
• InChiKey: NFISSTVAZSIYAT-UHFFFAOYSA-N

物化性质

• 熔点：
  39-42oC
• 沸点：
  297.3±35.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  双(3-甲基-2-噻吩基)甲酮 在 sodium hydroxide 、 氢溴酸 、 potassium carbonate 、 magnesium 、 potassium iodide 作用下， 以 乙醇 、 溶剂黄146 、 丙酮 为溶剂， 反应 51.5h， 生成 噻加宾
  参考文献：
  名称：

  The synthesis of novel GABA uptake inhibitors. 1. Elucidation of the structure-activity studies leading to the choice of (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid (Tiagabine) as an anticonvulsant drug candidate

  摘要：

  A series of different synthetic approaches to novel GABA uptake inhibitors are described, leading to examples which are derivatives of nipecotic acid and guvacine, substituted at nitrogen by 4,4-diaryl-3-butenyl or 2-(diphenylmethoxy)ethyl moieties. The in vitro value for inhibition of [H-3]-GABA uptake in rat synaptosomes was determined for each compound. It was found that the most potent examples are those having a substituent in an ''ortho'' position in one or both aromatic/heteroaromatic groups. The majority of the compounds described are structurally related to tiagabine, (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid hydrochloride (NNC 05-0328) and some of the reasoning behind the selection of this compound as a drug candidate is summarized.

  DOI：

  10.1021/jm00064a005
• 作为产物：
  描述：

  3-甲基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 双(3-甲基-2-噻吩基)甲酮
  参考文献：
  名称：

  Formation of a trithia[5]helicene in an unexpected photoreaction of a methyl-substituted bis(dithienylethenyl)thiophene through a double sequence of 6π-electrocyclization/aromatization (dehydrogenation/demethylation)

  摘要：

  Photochemical reactions of 2,5-bis[2,2-di(thien-2-yl)ethenyl]thiophene (1a) and its tetramethyl derivative 1b, under direct photoexcitation, and photoinduced electron-transfer conditions, were studied. Our initial prediction was that 1b would undergo a photoreaction as part of a reversible photochromic system, while a reaction of its non-methyl substituted analog 1a would undergo a typical double sequence of 6 pi-electrocyclization (6 pi-EC)/aromatization (AR) (double dehydrogenation, -2H) to give 7,11-di(thien-2-yl)trithia[5]helicene (2a). In fact, we observed that photoirradiation of 1b leads to formation of the 7,11-bis(3-methylthien-2-yl)trithia[5]helicene (2b). In this process, 2b is formed via a double sequence of 6 pi-EC/AR (dehydrogenation/demethylation, -H/-Me). Moreover, the yield of formation of 2b is much higher than that of 2a, which reacts through a double sequence of 6 pi-EC/AR (-2H). Thus, this photochemically-induced paradoxical cascade reaction based on the newly uncovered reactivity serves as an efficient method to construct the trithia[5]helicene framework. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2015.10.012

文献信息

• Novel compounds, their preparation and use
  申请人：Jeppesen Lone

  公开号：US20050070583A1

  公开（公告）日：2005-03-31

  Novel compounds of the general formula (I), the use of these compounds as pharmaceutical compositions, pharmaceutical compositions comprising the compounds and methods of treatment employing these compounds and compositions. The present compounds may be useful in the treatment and/or prevention of conditions mediated by Peroxisome Proliferator-Activated Receptors (PPAR), in particular the PPARδ suptype.

  通用公式（I）的新化合物，这些化合物作为药物组成物的用途，包含这些化合物的药物组成物以及使用这些化合物和组成物的治疗方法。这些化合物可能在治疗和/或预防由过氧化物酶体增殖物激活受体（PPAR）介导的疾病中有用，特别是PPARδ亚型。
• N-(butenyl substituted) azaheterocyclic carboxylic acids
  申请人：Novo Nordisk A/S.

  公开号：US05010090A1

  公开（公告）日：1991-04-23

  1-Aminobut-3-en derivatives having optionally substituted furanyl, thienyl, pyridyl and/or pyrrolyl in the 4-position and 3-carboxypiperidin-1-yl, 3-carboxytetrahydropyrid-1-yl or 3 carboxymethylpyrrolidin-1-yl in the 1-position potentiate GABA-ergic neurotransmission.

  在1-位置具有3-羧基哌啶-1-基，3-羧基四氢吡啶-1-基或3-羧甲基吡咯烷-1-基，并在4-位置上选择性地取代呋喃基，噻吩基，吡啶基和/或吡咯基的1-氨基丁-3-烯衍生物，能够增强GABA能神经递质的传递。
• 噻加宾的制备方法及其前体化合物
  申请人：扬子江药业集团四川海蓉药业有限公司

  公开号：CN102827152A

  公开（公告）日：2012-12-19

  本发明涉及噻加宾的制备方法及其前体化合物。具体公开了一种噻加宾及其消旋体和S-构型产物的制备方法，其特征在于其中包括使化学式V的化合物与化学式VI的化合物反应制备化学式VII的化合物的步骤： 其中，X选自由氯、溴和碘组成的组中；R 1 为选自由氢、取代或未取代的烷基、取代或未取代的芳基组成的组中的基团，优选为氢、C1-C4烷基或苄基，更优选为氢、甲基、乙基或苄基。本发明的方法通过改变手性哌啶甲酸酯的烷基化方法，利用酰基化转变完成烷基化，从而大大提高手性哌啶甲酸酯的利用率，保持整个N-烷基化总收率80％以上。
• New nitromethyl ketones, process for preparing them and compositions containing them
  申请人：Merck Patent GmbH

  公开号：US20030171422A1

  公开（公告）日：2003-09-11

  The present invention relates to the compounds of formula: 1 in which R 1 , R 2 , R 3 , E, A, X, Z, p and n are as defined herein. These compounds are aldose reductase inhibitors.

  本发明涉及公式1中的化合物：其中R1，R2，R3，E，A，X，Z，p和n的定义如本文所述。这些化合物是醛糖还原酶抑制剂。
• NITROMETHYL KETONES, PROCESS FOR PREPARING THEM AND COMPOSITIONS CONTAINING THEM
  申请人：——

  公开号：US20030069312A1

  公开（公告）日：2003-04-10

  The present invention relates to the compounds of formula: 1 in which R 1 , R 2 , R 3 , E, A, X, Z, p and n are as defined herein. These compounds are aldose reductase inhibitors.

  本发明涉及以下式子的化合物：1式中R1、R2、R3、E、A、X、Z、p和n的定义如本文所述。这些化合物是醛糖还原酶抑制剂。