2-(thiophene-2-yl)acetic anhydride | 63521-93-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(thiophene-2-yl)acetic anhydride
• 英文别名: 2-(thiophen-2-yl)acetic anhydride；3-thienylacetic acid anhydride；thienylacetic anhydride；(Thiophen-2-yl)acetic anhydride；(2-thiophen-2-ylacetyl) 2-thiophen-2-ylacetate
• CAS: 63521-93-7
• 化学式: C₁₂H₁₀O₃S₂
• 分子量: 266.342
• InChiKey: AFJUXKJRISUSPT-UHFFFAOYSA-N

物化性质

• 沸点：
  396.8±37.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(thiophene-2-yl)acetic anhydride 、 二苯二硫醚 生成 2-((phenylthio)methyl)thiophene
  参考文献：
  名称：

  Free radical reactions initiated by organocobalt complexes. A new method for the degradation of carboxylic acids tofunctionalised nor-alkanes via acylcobalt salophen intermediates.

  摘要：

  DOI：

  10.1016/s0040-4039(00)80190-2
• 作为产物：
  描述：

  2-噻吩乙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 甲苯 为溶剂， 反应 0.25h， 生成 2-(thiophene-2-yl)acetic anhydride
  参考文献：
  名称：

  不对称异硫脲催化的形式 [3+2] 烯醇铵与恶氮丙啶的环加成反应

  摘要：

  描述了一种高度对映选择性的路易斯碱催化的烯醇铵和恶氮丙啶的形式 [3+2] 环加成，以高收率得到立体定义的恶唑烷-4-酮。在该过程中使用富含对映体的恶氮丙啶导致与异硫脲催化剂的匹配/错配效应，并允许以高 dr、产率和ee合成顺式或反立体定义的恶唑烷-4-酮。此外，恶唑烷-4-酮产品已被衍生化，以提供功能化的对映体富集结构单元。

  DOI：

  10.1002/chem.201501271

文献信息

• 6.alpha., .beta.-Substituted penicillin derivatives
  申请人：Merck & Co., Inc.

  公开号：US04035359A1

  公开（公告）日：1977-07-12

  Novel 6-methoxy and 6-thioalkyl-6-acylamido-penicillanic acids and their non-toxic pharmaceutically-acceptable salts, esters and amides which are useful as antibiotics. The products are prepared by treating an ester of 6-substituted-6-aminopenicillanic acid with an acylating agent followed by removal of the ester group. Also disclosed are novel intermediates.

  新型的6-甲氧基和6-硫代烷基-6-酰胺基-青霉烷酸及其无毒的药用可接受盐、酯和酰胺，可用作抗生素。这些产品是通过将6-取代-6-氨基青霉烷酸酯与酰化剂处理后去除酯基而制备的。还披露了新型中间体。
• A CONVENIENT METHOD FOR SYNTHESIS OF SYMMETRICAL ACID ANHYDRIDES FROM CARBOXYLIC ACIDS WITH TRICHLOROACETONITRILE AND TRIPHENYLPHOSPHINE
  作者：Joonggon Kim、Doo Ok Jang

  DOI：10.1081/scc-100000529

  日期：2001.1

  Various carboxylic acids are converted into the corresponding carboxylic acid anhydrides treated with trichloroacetonitrile and triphenylphosphine in the presence of triethylamine at room temperature.

  在室温下，在三乙胺的存在下，各种羧酸被转化为相应的羧酸酐，用三氯乙腈和三苯基膦处理。
• Derivatives of 6-aminopenicillanic acid
  申请人：Merck & Co., Inc.

  公开号：US04071529A1

  公开（公告）日：1978-01-31

  Novel 6-methoxy and 6-thioalkyl-6-acylamidopenicillanic acids and their non-toxic pharmaceutically-acceptable salts, esters and amides which are useful as antibiotics. The products are prepared by treating an ester of 6-substituted-6-aminopenicillanic acid with an acylating agent followed by removal of the ester group. Also disclosed are novel intermediates.

  新型的6-甲氧基和6-硫代烷基-6-酰胺基青霉烷酸及其无毒的药用可接受盐、酯和酰胺，可用作抗生素。这些产品是通过将6-取代-6-氨基青霉烷酸酯与酰化剂处理，然后去除酯基而制备的。还披露了新型中间体。
• α-Aminothiazole-γ-aminobutanoic amides as potent, small molecule CCR2 receptor antagonists
  作者：Changyou Zhou、Liangqin Guo、William H. Parsons、Sander G. Mills、Malcolm MacCoss、Pasquale P. Vicario、Hans Zweerink、Margaret A. Cascieri、Martin S. Springer、Lihu Yang

  DOI：10.1016/j.bmcl.2006.10.059

  日期：2007.1

  A series of racemic and homochiral alpha-aminothiazole-gamma-aminobutyroamides that display high affinities for human and murine CCR2 and functional antagonism by inhibition of monocyte recruitment are described. A representative example is (2S)2- [2-(acetyl amino)-1, 3-thiazol-4-yl]-N-[3-methyl-5-(trifluoromethyl)benzyl]-4-(4-phenylpiperidin-1-yl)butanamide, which shows 5 nM affinity for human monocytes and CHO cells expressing the human CCR2b receptor. It also inhibited MCP-1 initiated chemotaxis of human monocytes with an IC50 of 0.69 nM. (c) 2006 Elsevier Ltd. All rights reserved.
• Isothiourea-Catalyzed Asymmetric Synthesis of β-Lactams and β-Amino Esters from Arylacetic Acid Derivatives and <i>N</i>-Sulfonylaldimines
  作者：Siobhan R. Smith、James Douglas、Hugues Prevet、Peter Shapland、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1021/jo402590m

  日期：2014.2.21

  The isothiourea HBTM-2.1 (5 mol %) catalyzes the asymmetric formal [2 + 2] cycloaddition of both arylacetic acids (following activation with tosyl chloride) and preformed 2-arylacetic anhydrides with N-sulfonylaldimines, generating stereo-defined 2,3-diaryl-beta-amino esters (after ring-opening) and 3,4-diaryl-anti-beta-lactams, respectively, with high diastereocontrol (up to >95:5 dr) and good to excellent enantiocontrol. Deprotection of the N-tosyl substituent within the beta-lactam framework was possible without racemization by treatment with SmI2.