ethyl 3-(phenylthio)propiolate | 80404-54-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 3-(phenylthio)propiolate
• 英文别名: Ethyl 3-phenylsulfanylprop-2-ynoate
• CAS: 80404-54-2
• 化学式: C₁₁H₁₀O₂S
• 分子量: 206.265
• InChiKey: JGDVRPSYQMQGLV-UHFFFAOYSA-N

物化性质

• 沸点：
  304.8±25.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-(phenylthio)propiolate 在 二甲基二环氧乙烷 作用下， 以 氯仿 、 丙酮 为溶剂， 生成 Ethyl 3-(benzenesulfonyl)bicyclo[2.2.2]octa-2,5-diene-2-carboxylate
  参考文献：
  名称：

  Thioindigo precursor: control of polymorph of thioindigo

  摘要：

  2,2'-Bi[-3(2H)-thioplienon]ylidene with two bicyclo[2.2.2]-octadiene moieties was quantitatively converted to thioindigo by the retro-Diels-Alder reaction. The thioindigo solid obtained from the precursor had the P2(1)/c structure which was different from the commercial thioindigo samples (P2(1)/n). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.028
• 作为产物：
  描述：

  苯次磺酰氯 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 生成 ethyl 3-(phenylthio)propiolate
  参考文献：
  名称：

  2-(三甲基甲硅烷基)乙基苯次磺酸盐和苯硒酸盐的合成及其在四丁基氟化铵存在下与一些亲电试剂的反应

  摘要：

  在四丁基氟化铵 (TBAF) 存在下，使 2-(三甲基甲硅烷基) 乙基苯磺酸盐与几种卤化物反应，得到相应的苯基亚砜作为主要产物。2-(三甲基甲硅烷基)乙基苯硒酸酯和几种卤化物与TBAF反应，主要产物为相应的醇。

  DOI：

  10.1246/bcsj.64.702

文献信息

• Regiocontrolled Synthesis of Ring-Fused Thieno[2,3-c]pyrazoles through 1,3-Dipolar Cycloaddition of Nitrile Imines with Sulfur-Based Acetylenes
  作者：Jay Zumbar Chandanshive、Bianca Flavia Bonini、Denis Gentili、Mariafrancesca Fochi、Luca Bernardi、Mauro Comes Franchini

  DOI：10.1002/ejoc.201001048

  日期：2010.11

  1,3-Dipolar cycloadditions of C-carboxymethyl-N-arylnitrile imines with substituted acetylenes bearing thiol or sulfone groups were studied. The sulfur controls the regiochemistry of the reaction, and this protocol was applied to the synthesis of ring-fused thieno[2,3-c]pyrazoles.

  研究了 C-羧甲基-N-芳基腈亚胺与带有硫醇或砜基团的取代乙炔的 1,3-偶极环加成反应。硫控制了反应的区域化学，该方案被应用于稠环噻吩并 [2,3-c] 吡唑的合成。
• Batrachotoxin Analogues, Compositions, Uses, and Preparation Thereof
  申请人：Du Bois Justin

  公开号：US20140171410A1

  公开（公告）日：2014-06-19

  Compounds relating to batrachotoxin are provided, in particular analogues that modulate the activity of sodium channels. Also provided are pharmaceutical compositions comprising compounds of the invention and a pharmaceutically acceptable carrier, including vehicles that modulate transdermal permeation of the compound. The subject compounds are useful in treatments, including treatments to reduce neuronal activity or to bring about muscular relaxation. The compounds also find use in the treatment of subjects suffering from a voltage-gated sodium channel-enhanced ailment or from pain. Further methods are provided for the preparation of the batrachotoxin-related compounds.

  提供了与蝙蝠毒素相关的化合物，特别是能够调节钠通道活性的类似物。还提供了包含本发明化合物的药物组合物以及药用辅料，包括能够调节化合物经皮渗透的载体。所述化合物可用于治疗，包括用于减少神经活动或引起肌肉松弛的治疗。这些化合物还用于治疗患有电压门控钠通道增强病症或疼痛的患者。还提供了用于制备与蝙蝠毒素相关化合物的方法。
• Palladium-Catalyzed Regio- and Stereoselective Coupling–Addition of Propiolates with Arylsulfonyl Hydrazides: A Pattern for Difunctionalization of Alkynes
  作者：Lixin Liu、Kang Sun、Lebin Su、Jianyu Dong、Lei Cheng、Xiaodong Zhu、Chak-Tong Au、Yongbo Zhou、Shuang-Feng Yin

  DOI：10.1021/acs.orglett.8b01585

  日期：2018.7.6

  A new pattern for difunctionalization of alkynes via a palladium-catalyzed regio- and stereoselective coupling–addition of propiolates with arylsulfonyl hydrazides is disclosed. The approach enables the synthesis of various highly functionalized (E)-vinylsulfones in satisfactory yields. Arylsulfonyl hydrazides act as both aryl and sulfonyl sources via selective cleavage of Ar(C)–S and S–N bonds, which

  公开了通过钯催化的区域和立体选择性偶合（炔丙基磺酰肼与丙酸酯的加成反应）使炔烃双官能团化的新模式。该方法能够以令人满意的产率合成各种高度官能化的（E）-乙烯基砜。芳基磺酰肼可通过选择性裂解Ar（C）-S和S-N键同时充当芳基和磺酰基来源，同时将这些键结合到炔烃分子的末端碳原子上。
• A heterogeneous copper(I)-catalyzed aerobic oxidative cross-dehydrogenative coupling of terminal alkynes with thiols leading to alkynyl sulfides
  作者：Zhiqiang Fang、Wen He、Mingzhong Cai、Yang Lin、Hong Zhao

  DOI：10.1016/j.tetlet.2015.09.153

  日期：2015.11

  A heterogeneous copper-catalyzed direct oxidative cross-dehydrogenative coupling of terminal alkynes with thiols was achieved in DMSO at 70 °C in the presence of an MCM-41-supported bidentate nitrogen copper(I) complex [MCM-41-2N-CuCl] and K2CO3 under an atmosphere of O2, yielding selectively a variety of alkynyl sulfides in good to excellent yields. This heterogeneous copper catalyst can be easily

  在MSO-41负载的双齿氮铜（I）络合物[MCM-41-2N-CuCl]的存在下，在DMSO中于70°C的条件下，末端炔烃与硫醇的异质铜催化直接氧化交叉脱氢偶联反应和在O 2气氛下的K 2 CO 3，以良好至优异的产率选择性地产生各种炔基硫化物。该多相铜催化剂可通过简单的过滤容易地回收并循环10次而活性没有降低。
• Preparation and Diels-Alder reactivity of ethyl-β-phenylsulfonylpropiolate
  作者：Ming Shen、Arthur G. Schultz

  DOI：10.1016/s0040-4039(01)81901-8

  日期：1981.1