ethyl β-(phenylsulfonyl)propiolate | 80404-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl β-(phenylsulfonyl)propiolate
• 英文别名: ethyl-β-phenylsulonylpropiolate；ethyl 3-(phenylsulfonyl)propiolate；ethyl phenylsulfonylpropiolate；Ethyl 3-(benzenesulfonyl)prop-2-ynoate
• CAS: 80404-53-1
• 化学式: C₁₁H₁₀O₄S
• 分子量: 238.264
• InChiKey: HYMRHMPEQXVOIG-UHFFFAOYSA-N

物化性质

• 沸点：
  363.9±25.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl β-(phenylsulfonyl)propiolate 在 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 Ethyl 3-(2-ethoxy-2-oxoethyl)sulfanylbicyclo[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：

  S-苯基硫代苯基砜 在 二甲基二环氧乙烷 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 ethyl β-(phenylsulfonyl)propiolate
  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

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。
• Modular synthesis of the pentacyclic core of batrachotoxin and select batrachotoxin analogue designs
  作者：A. Sloan Devlin、J. Du Bois

  DOI：10.1039/c2sc21723f

  日期：——

  Pentacyclic analogues of the potent voltage-gated sodium ion channel agonist batrachotoxin can be accessed through an intermediate furan by exploiting Diels-Alder cycloaddition reactions with ring-strained dienophiles. The use of 3-bromofuran as a 1,2-dianion equivalent, the application of carbamate reductive N-alkylation for homomorpholine ring assembly, and the demonstration of CsF as an effective

  强大的电压门控钠离子通道激动剂巴曲毒素的五环类似物可通过利用呋喃环与Diels-Alder环加成反应与环应变的亲二烯体接触而通过中间呋喃获得。使用3-溴呋喃作为1，2-阴离子等效物，应用氨基甲酸酯还原性N-烷基化作用制备同型吗啉环，以及证明CsF作为产生苯并，环己和相关亲二烯体的有效试剂的研究强调了这项工作。
• Skeletal Transformation of Unactivated Arenes Enabled by a Low-Temperature Dearomative (3 + 2) Cycloaddition
  作者：Sajan Pradhan、Fahimeh Mohammadi、Jean Bouffard

  DOI：10.1021/jacs.3c02314

  日期：2023.6.7

  exchange of the ring carbons: a two-carbon fragment from the original aromatic ring is replaced with another from the incoming dienophile, introducing an unconventional disconnection for the synthesis of ubiquitous aromatic building blocks. Applications of this two-step sequence to the preparation of substituted acenes, isotopically labeled molecules, and medicinally relevant compounds are demonstrated

  像苯这样的简单芳香族化合物是丰富的原料，其衍生物的制备主要从亲电取代反应开始，或者较少见的是还原反应。它们的高稳定性使它们特别不愿意在普通反应条件下参与环加成反应。在这里，我们展示了 1,3-diaza-2-azoniaallene 阳离子在室温下与未活化的苯衍生物进行形式 (3 + 2) 环加成的特殊能力，提供了多克级的热稳定脱芳构化加合物。容忍极性官能团的环加成激活环以进一步细化。在用亲二烯体处理时，环加合物会经历 (4 + 2) 环加成-环逆转级联反应，产生取代或稠合的芳烃，包括萘衍生物。整个序列通过环碳的交换导致芳烃的转化：来自原始芳环的双碳片段被来自进入的亲双烯体的另一个取代，为普遍存在的芳香结构单元的合成引入非常规的断开。证明了该两步序列在制备取代并苯、同位素标记分子和医学相关化合物中的应用。