(2-cyanoethyl) propiolate | 14451-18-4

• 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-cyanoethyl) propiolate
• 英文别名: 2-Cyanoaethylpropiolat；propynoic acid 2-cyanoethyl ester；2-cyanoethyl prop-2-ynoate
• CAS: 14451-18-4
• 化学式: C₆H₅NO₂
• 分子量: 123.111
• InChiKey: PLZWHDPSWYBXDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-cyanoethyl) propiolate 在 甲醇 、 ammonium acetate 、 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 2.0h， 生成 4-(3,5-dichloro-4-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-cinnamyl ester
  参考文献：
  名称：

  Discovery and evaluation of selective N-type calcium channel blockers: 6-Unsubstituted-1,4-dihydropyridine-5-carboxylic acid derivatives

  摘要：

  A structure-activity relationship study of 6-unsubstituted-1,4-dihydropyridine and 2,6-unsubstituted-1,4-dihydropyridine derivatives was conducted in an attempt to discover N-type calcium channel blockers that were highly selective over L-type calcium channel blockers. Among the tested compounds, (+)-4-(3,5-dichloro-4-methoxy-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-cinnamyl ester was found to be an effective and selective N-type calcium channel blocker with oral analgesic potential. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.051
• 作为产物：
  描述：

  3-羟基丙腈 、 丙炔酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2-cyanoethyl) propiolate
  参考文献：
  名称：

  CF2Br2 的自由基-极性交叉实现三重裂解：多组分串联环化生成 3-氟吡唑

  摘要：

  非常需要详细阐述用于获取多种氟化杂环的分步经济和催化方法。本文描述了通过使用CF 2 Br 2作为新型C1F1合成子实现自由基-极性交叉的三组分环化成多取代的氟吡唑。机理实验表明，反应中间体偕-二氟乙烯基亚胺离子的原位生成是这一转变的关键。该方案解锁了 CF 2 Br 2的新颖反应性，并为氟化学增加了重要的合成价值。

  DOI：

  10.1021/acs.orglett.3c02305

文献信息

• Dihydropyridine derivative
  申请人：Ajinomoto Co., Inc.

  公开号：US06350766B1

  公开（公告）日：2002-02-26

  Dihydropyridine derivatives of the following formula, analogs thereof and pharmaceutically acceptable salts thereof have an activity of selectively inhibiting the action of N-type calcium channel. They are used as remedies for various diseases relating to the N-type calcium channel such as encephalopathies caused by the ischemia in the acute phase after the onset of cerebral infarction, cerebral hemorrhage or the like, Alzheimer's disease, etc.

  二氢吡啶衍生物具有以下结构式，其类似物和药学上可接受的盐具有选择性抑制N型钙通道作用的活性。它们被用作治疗与N型钙通道相关的各种疾病，如脑梗死发作后急性期内由缺血引起的脑病、脑出血或类似疾病、阿尔茨海默病等。
• A mild and efficient Si (111) surface modification via hydrosilylation of activated alkynes
  作者：Yang Liu、Shoko Yamazaki、Shinichi Yamabe、Yoshihiro Nakato

  DOI：10.1039/b511535c

  日期：——

  A new Si surface modification with organic groups via hydrosilylation at room temperature is reported. A hydrogen-terminated Si (111) surface was reacted with activated alkynes such as propiolate esters, propiolic acid, but-3-yne-2-one, propiolonitrile and phenylacetylene at room temperature for 24–40 h to give modified surfaces. The coverage ratio was estimated to be 31–56% by XPS analysis. This surface modification method is mild, highly efficient and procedurally simple. The novel surfaces modified with various organic functional groups are expected to have interesting utilities.

  报道了一种新的硅表面改性方法，通过室温下的氢化硅烷化实现有机基团的引入。将氢终止的硅（111）表面与活化炔（如丙酸酯、丙炔酸、丁-3-炔-2-酮、丙腈和苯基乙炔）在室温下反应24至40小时，得到改性的表面。通过XPS分析，覆盖率估计为31-56%。这种表面改性方法温和、高效且程序简单。预期这些改性后的新型表面具有有趣的应用。
• Selective difunctionalization of electron-deficient alkynes: access to (<i>E</i>)-2-iodo-3-(methylthio)acrylate
  作者：Ling-Hui Lu、Guangchuan Ou、Xiongjie Zhao、Yufei Wang、Xuelian Chen、Wenjun Liao、Shundan Li、Chao Wu

  DOI：10.1039/d1ob01287h

  日期：——

  A convenient and efficient approach to (E)-2-iodo-3-(methylthio)acrylate has been developed through direct iodothiomethylation of alkynes with aqueous HI and DMSO under mild conditions. This novel protocol has demonstrated a unique difunctionalization of electron-deficient alkynes with a broad substrate scope and excellent functional-group tolerance. Preliminary mechanistic studies indicated that prior

  通过在温和条件下用 HI 和 DMSO 水溶液直接碘硫甲基化炔烃，开发了一种方便有效的 ( E )-2-iodo-3-(甲硫基)丙烯酸酯方法。这种新颖的协议证明了缺电子炔烃的独特双功能化，具有广泛的底物范围和出色的官能团耐受性。初步机理研究表明，先对炔烃进行二碘化，然后用原位产生的 DMS 进行亲核取代，导致形成 ( E )-2-iodo-3-(methylthio) 丙烯酸酯。
• Photographic products and processes employing novel nondiffusible
  申请人：Eastman Kodak Company

  公开号：US04385104A1

  公开（公告）日：1983-05-24

  Photographic elements, diffusion transfer assemblages and processes are described which employ a novel nondiffusible compound having a releasable 6-(2-thienylazo)-3-pyridinol cyan dye moiety or precursor thereof, the compound containing: (a) in the 3-position of the thienylazo moiety a carboxy group, a salt thereof or a hydrolyzable precursor thereof; and (b) a ballasted carrier moiety which is capable of releasing the diffusible 6-(2-thienylazo)-3-pyridinol dye moiety or precursor thereof under alkaline conditions.

  描述了使用一种新型的不可扩散化合物的摄影元素、扩散转移组合物和过程，该化合物具有可释放的6-(2-噻吩基偶氮)-3-吡啶酚青色染料基团或其前体，该化合物包含：(a) 在噻吩基偶氮基团的3位上的羧基、其盐或可水解前体；以及(b) 能够在碱性条件下释放可扩散的6-(2-噻吩基偶氮)-3-吡啶酚染料基团或其前体的配基载体基团。
• Ultrasound-promoted Brønsted acid ionic liquid-catalyzed hydrothiocyanation of activated alkynes under minimal solvent conditions
  作者：Chao Wu、Ling-Hui Lu、Ai-Zhong Peng、Guo-Kai Jia、Cun Peng、Zhong Cao、Zilong Tang、Wei-Min He、Xinhua Xu

  DOI：10.1039/c8gc00491a

  日期：——

  protocol for the synthesis of Z-vinyl thiocyanates through ultrasound-promoted Brønsted acid ionic liquid-catalyzed hydrothiocyanation of activated alkynes under minimal solvent conditions has been developed. This process effectively avoids the use of organic solvents, metal catalysts and harsh reaction conditions. This reaction shows attractive characteristics such as operational simplicity, broad substrate

  通过使用水作为氢源，已开发了一种环保且实用的方案，可在最小的溶剂条件下通过超声促进的布朗斯台德酸离子液体催化的炔烃氢硫氰化来合成Z-乙烯基硫氰酸酯。该过程有效地避免了使用有机溶剂，金属催化剂和苛刻的反应条件。该反应显示出诱人的特性，例如操作简便，具有良好的优良收率的宽范围的底物，易于规模化生产和高能源效率以及可回收和可重复使用的催化剂。