3-(3-thienyl)propanenitrile | 21822-40-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-(3-thienyl)propanenitrile
• 英文别名: 3-(3-thienyl)propionitrile；3-(thiophen-3-yl)propanenitrile；3-thiophen-3-yl-propionitrile；3-Thiophen-3-ylpropanenitrile
• CAS: 21822-40-2
• 化学式: C₇H₇NS
• 分子量: 137.205
• InChiKey: WQXDXJIWDZQYSG-UHFFFAOYSA-N

物化性质

• 沸点：
  136-138 °C(Press: 14 Torr)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-thienyl)propanenitrile 在 sodium acetate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 生成 ((Z)-2-Cyano-3-thiophen-3-yl-propenylamino)-acetic acid methyl ester
  参考文献：
  名称：

  嘌呤核苷磷酸化酶抑制剂的基于结构的设计。1. 9-脱氮鸟嘌呤的9-（芳基甲基）衍生物。

  摘要：

  嘌呤核苷磷酸化酶（PNP，EC 2.4.2.1）是一种挽救酶，对免疫系统中T细胞介导的部分很重要，因此是重要的治疗靶标。本文介绍了有效，竞争性PNP抑制剂的设计，合成和酶学评估。在迭代过程中使用酶的三维结构设计潜在的抑制剂，该过程涉及交互式计算机图形来模拟天然酶及其与抑制剂的复合物，基于蒙特卡洛的构象搜索和能量最小化。酶/抑制剂复合物的研究用于确定合成努力的优先级。然后通过确定它们的IC 50值并通过使用差分傅立叶图的X射线衍射分析来评估所得化合物。以这种方式，我们开发了一系列有效的，可透过膜的9-（芳基甲基）-9-脱氮嘌呤（2-氨基-7-（芳基甲基）-4H-吡咯并[3,2-d]-嘧啶-4-酮）酶的抑制剂。这些化合物的IC50值范围为17至270 nM（在1 mM磷酸盐中），其中9-（3,4-二氯苄基）-9-脱氮鸟嘌呤是最有效的抑制剂。X射线分析解释了芳基的作用，并揭示了相对于8-氨基鸟嘌

  DOI：

  10.1021/jm00053a008
• 作为产物：
  描述：

  噻吩-3-乙醇 在 四氯化碳 、 18-冠醚-6 、 三丁基膦 作用下， 以 乙腈 为溶剂， 反应 37.0h， 生成 3-(3-thienyl)propanenitrile
  参考文献：
  名称：

  通过与高电荷的阳离子醌-紫精聚合物或阳离子聚（3-紫3-噻吩）静电结合的阴离子醌捕获电荷

  摘要：

  Charge associated with quinone reduction is trapped at low pH in systems composed of sulfonated anthraquinones electrostatically bound to a polymer derived from a monomer consisting of a quinone unit flanked by two viologen units. Each monomer repeat unit carries 6 equiv of positive charge which can be charge compensated by monosulfonated anthraquinone to yield a quinone:viologen ratio of nearly 7:2. At low pH, electrostatic binding is persistent, and the amount of trapped charge is 90% of the theoretical maximum. Some of the electrostatically bound quinone can be replaced with Fe(CN)63- to allow mediated release of trapped charge via the Fe(CN)63-/4- redox couple. I- is blocked from entering the polymer and thus does not mediate release of charge. Electrostatic binding of anionic quinones to a thiophene polymer with pendant viologen units has also been demonstrated. This polymer system has the unique property of having built-in mediators for both the reduction (charge trapping) and oxidation (charge release) of the electrostatically bound anthraquinone.

  DOI：

  10.1021/j100124a045

文献信息

• Antiinflammation agents
  申请人：Tularik Inc.

  公开号：US20040097485A1

  公开（公告）日：2004-05-20

  Compounds, compositions and methods that are useful in the treatment of inflammatory, immunoregulatory, metabolic, infectious and cell proliferative diseases or conditions are provided herein. In particular, the invention provides compounds which modulate the expression and/or function of proteins involved in inflammation, metabolism, infection and cell proliferation. The subject compounds contain a fused heterobicyclic ring.

  本文提供了在治疗炎症、免疫调节、代谢、感染和细胞增殖性疾病或状况中有用的化合物、组合物和方法。具体而言，本发明提供了调节参与炎症、代谢、感染和细胞增殖的蛋白质的表达和/或功能的化合物。所述化合物包含一个融合的异双环环。
• Monoalkylation of Acetonitrile by Primary Alcohols Catalyzed by Iridium Complexes
  作者：Bruno Anxionnat、Domingo Gomez Pardo、Gino Ricci、Janine Cossy

  DOI：10.1021/ol2015972

  日期：2011.8.5

  The monoalkylation of acetonitrile by primary alcohols was achieved in a one-pot sequence in the presence of iridium catalysts. A diversity of nitriles has been obtained from aryl- and alkyl-methanols in excellent yield.

  在铱催化剂的存在下，乙醇被伯醇单烷基化的反应是按一锅法完成的。从芳基和烷基甲醇中获得了各种腈，收率很高。
• 9-subtituted-8-unsubstituted-9-deazaguanines
  申请人：BioCryst Pharmaceuticals, Inc.

  公开号：US05565463A1

  公开（公告）日：1996-10-15

  The specification discloses the compounds of formula I ##STR1## wherein (a) --CH.sub.2 Ar represents ##STR2## in which R.sub.1 represents hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, benzyloxy, hydroxy or trifluoromethyl; and R.sub.2 represents hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, benzyloxy, hydroxy or trifluoromethyl; provided that R.sub.2 represents hydrogen or C.sub.1 -C.sub.3 -alkyl if R.sub.1 represents trifluoromethyl, or that R.sub.1 represents hydrogen or C.sub.1 -C.sub.3 -alkyl if R.sub.2 represents trifluoromethyl; or (b) --CH.sub.2 Ar represents ##STR3## in which X represents sulfur or oxygen and in which attachment to the thiophene or furan ring is at the 2- or 3-position; and tautomers thereof; as purine nucleoside phosphorylase inhibitors.

  该规范公开了式I的化合物 ##STR1## 其中(a) --CH.sub.2 Ar代表 ##STR2## 其中R.sub.1代表氢，卤素，C.sub.1-C.sub.3-烷基，C.sub.1-C.sub.3-烷氧基，苯甲氧基，羟基或三氟甲基;而R.sub.2代表氢，卤素，C.sub.1-C.sub.3-烷基，C.sub.1-C.sub.3-烷氧基，苯甲氧基，羟基或三氟甲基；但是如果R.sub.1代表三氟甲基，则R.sub.2代表氢或C.sub.1-C.sub.3-烷基，或者如果R.sub.2代表三氟甲基，则R.sub.1代表氢或C.sub.1-C.sub.3-烷基；或(b) --CH.sub.2 Ar代表 ##STR3## 其中X代表硫或氧，并且附着在噻吩或呋喃环的2-或3-位置；以及它们的互变异构体；作为嘌呤核苷酸磷酸化酶抑制剂。
• Light‐Induced Divergent Cyanation of Alkynes Enabled by Phosphorus Radicals
  作者：Yanyan Zhang、Yunhong Han、Shengqing Zhu、Feng‐Ling Qing、Xiao‐Song Xue、Lingling Chu

  DOI：10.1002/anie.202210838

  日期：2022.12.12

  A photochemically induced selective and divergent cyanation reaction of alkynes, enabled by phosphorus radicals, is described. With the use of simple triarylphosphine as a co-catalyst, three cyanation reactions, including di-hydrocyanation, anti-Markovnikov hydrocyanation, and domino hydrocyanation/reduction, can be divergently achieved, furnishing a wide array of alkyl dinitriles, alkenyl nitriles

  描述了由磷自由基​​启用的光化学诱导的炔烃选择性和发散氰化反应。使用简单的三芳基膦作为助催化剂，可以发散地实现包括二氢氰化、反马尔可夫尼科夫氢氰化和多米诺氢氰化/还原在内的三种氰化反应，提供范围广泛的烷基二腈、烯基腈和烷基温和条件下的腈类。
• Charge trapping by anionic quinones electrostatically bound to a highly charged cationic quinone-viologen polymer or a cationic poly(3-viologenthiophene)
  作者：Christopher T. Hable、Richard M. Crooks、James R. Valentine、Richard Giasson、Mark S. Wrighton

  DOI：10.1021/j100124a045

  日期：1993.6

  Charge associated with quinone reduction is trapped at low pH in systems composed of sulfonated anthraquinones electrostatically bound to a polymer derived from a monomer consisting of a quinone unit flanked by two viologen units. Each monomer repeat unit carries 6 equiv of positive charge which can be charge compensated by monosulfonated anthraquinone to yield a quinone:viologen ratio of nearly 7:2. At low pH, electrostatic binding is persistent, and the amount of trapped charge is 90% of the theoretical maximum. Some of the electrostatically bound quinone can be replaced with Fe(CN)63- to allow mediated release of trapped charge via the Fe(CN)63-/4- redox couple. I- is blocked from entering the polymer and thus does not mediate release of charge. Electrostatic binding of anionic quinones to a thiophene polymer with pendant viologen units has also been demonstrated. This polymer system has the unique property of having built-in mediators for both the reduction (charge trapping) and oxidation (charge release) of the electrostatically bound anthraquinone.