3-(4-chlorophenyl)propioloyl chloride | 42122-34-9

• 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: 3-(4-chlorophenyl)propioloyl chloride
• 英文别名: p-chlorophenylpropiolyl chloride；(4-chloro-phenyl)-propioloyl chloride；(4-Chlor-phenyl)-propioloylchlorid；3-(4-chlorophenyl)prop-2-ynoyl chloride
• CAS: 42122-34-9
• 化学式: C₉H₄Cl₂O
• 分子量: 199.036
• InChiKey: GMVYDSQIALCWJC-UHFFFAOYSA-N

物化性质

• 沸点：
  284.0±42.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)propioloyl chloride 在 sodium hydroxide 、 碘 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 7.0h， 生成 5-(4-chlorophenyl)-2-phenylisothiazol-3(2H)-one
  参考文献：
  名称：

  2,5-Diarylisothiazolone: novel inhibitors of cytokine-induced cartilage destruction

  摘要：

  A series of 2,5-diarylisothiazolones is reported that inhibit the IL-lp-induced breakdown of bovine nasal septum cartilage in an organ culture assay. The synthesis and preliminary SAR of these compounds are described. These compounds represent a novel, nonpeptide lead series approach to the mediation of the chronic cartilage breakdown associated with arthritic disease. These compounds are relatively resistant to reductive metabolism by liver microsomal preparations and appear to inhibit cartilage breakdown by interfering with the proteolytic activation of matrix metalloproteinases. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00053-3
• 作为产物：
  描述：

  (4-氯苯基)-丙酸乙酯 在 sodium hydroxide 、 氯化亚砜 、 苄基三乙基氯化铵 作用下， 以 乙醚 、 水 为溶剂， 反应 126.0h， 生成 3-(4-chlorophenyl)propioloyl chloride
  参考文献：
  名称：

  Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 4. Stepwise construction of terminal 1, 3-diynes, conjugated diacetylenic esters and a triacetylenic ester

  摘要：

  Thirteen examples of stabilised alkynoyl ylides 6 have been prepared and are found, upon flash vacuum pyrolysis (FVP) at 500 degrees C, to undergo extrusion of Ph(3)PO to give the diacetylenic esters 7 in moderate yield. At 750 degrees C the same ylides afforded terminal 1.3-diynes 8 although often in poor yield. For R = 2-MeSC(6)H(4) both 7 and 8 undergo secondary loss of Me(.) and cyclisation to give 2-alkynylbenzothiophene derivatives 9 and 10 in low yield. The first example of an alkadiynoyl ylide 11 has been prepared and is converted by FVP at 500 degrees C into the triacetylenic ester 12.

  DOI：

  10.1039/p19940002461

文献信息

• Synthesis and fluorescence of the new environment-sensitive fluorophore 6-chloro-2,3-naphthalimide derivative
  作者：Alan R. Katritzky、Sevil Ozcan、Ekaterina Todadze

  DOI：10.1039/c000684j

  日期：——

  Convenient and efficient synthesis of a new environmentally sensitive chlorine-substituted 2,3-naphthalimide-based fluorophore is reported. Benzotriazole carboxyl group activation of the 6-chloro-fluorophore enabled quick labeling of free and Fmoc-protected amino acids. The photophysical properties of the compounds obtained include high quantum yields in solvents of different polarity: water, methanol, acetonitrile and hexane.

  报道了一种新型环境敏感型氯代2,3-萘酞亚胺基荧光团的高效便捷合成方法。通过苯并三唑羧基活化6-氯荧光团，可实现对游离氨基酸和Fmoc保护氨基酸的快速标记。所获得化合物的光物理性质包括在不同极性溶剂（水、甲醇、乙腈和己烷）中具有高量子产率。
• Asymmetric Catalysis in Liquid Confinement: Probing the Performance of Novel Chiral Rhodium–Diene Complexes in Microemulsions and Conventional Solvents
  作者：Max Deimling、Manuel Kirchhof、Barbara Schwager、Yaseen Qawasmi、Alex Savin、Tina Mühlhäuser、Wolfgang Frey、Birgit Claasen、Angelika Baro、Thomas Sottmann、Sabine Laschat

  DOI：10.1002/chem.201900947

  日期：2019.7.17

  studied using the 1,2‐addition of phenylboroxine (2) to N‐tosylimine 1 in the presence of [RhCl(C2H4)2]2 and chiral diene ligands as benchmark reaction. To get access to Rh complexes of different polarity, enantiomerically pure C2‐symmetric p‐substituted 3,6‐diphenylbicyclo[3.3.0]octadienes 4 and diastereomerically enriched unsymmetric norbornadienes 5 and 6 carrying either the Evans or the SuperQuat

  在[RhCl（C 2 H 4）2 ] 2存在下，以手性二烯配体为基准，研究了液相限制在不对称Rh催化中的作用，方法是将1,2,2-苯基环硼氧烷（2）加到N- tosylimine 1中。反应。为了获得不同极性的Rh络合物，对映体纯C 2对称的对位取代3,6-二苯基双环[3.3.0]辛二烯4和非对映体富集的不对称降冰片二烯5和6合成了携带Evans或SuperQuat辅助工具的产品。使用亲水性糖表面活性剂正辛基β- d-吡喃葡萄糖苷（C 8 G 1）配制包含等量H 2 O / KOH和甲苯/反应物的微乳液，以调解非极性反应物与KOH之间的混溶性激活Rh-二烯配合物。这种有组织的反应介质的突出特点是对温度不敏感，并且存在水和富含甲苯的隔室，通过小角度X射线散射（SAXS）证实了其区域大小为55Å。尽管双环辛二烯配体4 a，b，e在均相和微乳液条件下同样表现良好，配体4 c，d给出了不同的化学选
• Carbene-catalyzed LUMO activation of alkyne esters for access to functional pyridines
  作者：Chengli Mou、Jichang Wu、Zhijian Huang、Jun Sun、Zhichao Jin、Yonggui Robin Chi

  DOI：10.1039/c7cc08039e

  日期：——

  A carbene-catalyzed LUMO activation of α,β-unsaturated alkyne esters is reported. This catalytic process allows for effective reactions of alkyne esters with enamides to synthesize functional pyridines via simple protocols. A previously unexplored unsaturated alkyne acyl azolium intermediate is involved in the key step of the reaction.

  报道了卡宾催化的α，β-不饱和炔烃的LUMO活化。该催化过程允许炔烃酯与烯酰胺的有效反应，以通过简单的方案合成功能性吡啶。反应的关键步骤涉及先前未开发的不饱和炔烃酰基偶氮中间体。
• Synthesis of 4-Arylidenepyrazolones by a Gold-Catalyzed Cyclization/Arylidene Group Transfer Cascade of <i>N</i>-Propioloyl Hydrazones
  作者：Zong-Cang Ding、Hai-Tao Tang、Ren-Hao Li、Lu-Chuan Ju、Zhuang-Ping Zhan

  DOI：10.1021/acs.joc.5b01366

  日期：2015.9.18

  An efficient gold-catalyzed cyclization/arylidene group transfer cascade reaction of N-propioloyl hydrazones has been developed. This method provides a novel approach for the synthesis of various functionalized 4-arylidenepyrazolones.

  已经开发了一种有效的金催化的N-丙酰基酰azo的环化/亚芳基基团转移级联反应。该方法为合成各种官能化的4-亚芳基吡唑啉酮提供了一种新颖的方法。
• AlBr₃-Promoted stereoselective <i>anti-</i>hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: synthesis of 3,3-diarylpropenenitriles
  作者：Yelizaveta Gorbunova、Dmitry S Ryabukhin、Aleksander V Vasilyev

  DOI：10.3762/bjoc.17.180

  日期：——

  electron-rich arenes (Ar′H, benzene and its polymethylated derivatives) under the action of aluminum bromide (AlBr3, 6 equiv) at room temperature for 0.5–2 h result in the stereoselective formation of 3,3-diarylpropenenitriles (Ar(Ar′)C=CHCN) in yields of 20–64%, as products of mainly anti-hydroarylation of the acetylene bond. The obtained 3,3-diarylpropenenitriles in triflic acid CF3SO3H (TfOH) at room temperature

  3-芳基丙炔腈（ArC≡CCN）与富电子芳烃（Ar'H、苯及其多甲基化衍生物）在溴化铝（AlBr 3，6当量）的作用下在室温下反应 0.5-2 小时，得到立体选择性形成 3,3-二芳基丙烯腈 (Ar(Ar')C=CHCN)，产率为 20-64%，主要是乙炔键的反加氢芳基化产物。所得 3,3-二芳基丙烯腈在三氟甲磺酸 CF 3 SO 3 H (TfOH) 中在室温下 1 小时环化为 3-芳基茚酮，产率为 55-70%。