3-(2-萘基)-2-丙炔酸 | 4843-43-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-(2-萘基)-2-丙炔酸
• 英文名称: 3-(naphthalen-2-yl)propiolic acid
• 英文别名: 2-naphthylpropiolic acid；3-(2-Naphthyl)prop-2-ynoic acid；3-naphthalen-2-ylprop-2-ynoic acid
• CAS: 4843-43-0
• 化学式: C₁₃H₈O₂
• mdl: MFCD00181402
• 分子量: 196.205
• InChiKey: XWMRRMQMFPBLTP-UHFFFAOYSA-N

物化性质

• 熔点：
  145-147 °C(Solv: carbon tetrachloride (56-23-5))
• 沸点：
  411.7±18.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-萘基)-2-丙炔酸 在 sodium hydroxide 、 氯化亚砜 作用下， 以 乙醇 、 苯 为溶剂， 反应 9.0h， 生成
  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：

  (E)-3-(萘-2-基)丙烯酸 在 氢氧化钾 、 溴 作用下， 生成 3-(2-萘基)-2-丙炔酸
  参考文献：
  名称：

  由芳基丙酸制备多环芳烃

  摘要：

  DOI：

  10.1039/jr9540003659

文献信息

• One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na₂S₂O₈
  作者：Teppei Sasaki、Katsuhiko Moriyama、Hideo Togo

  DOI：10.3762/bjoc.14.22

  日期：——

  Various 4-aryl-3-bromocoumarins were smoothly obtained in moderate yields in one pot by treating 3-aryl-2-propynoic acids with diaryliodonium triflates and K2CO3 in the presence of CuCl, followed by the reaction with tetrabutylammonium bromide (TBAB) and Na2S2O8. The obtained 3-bromo-4-phenylcoumarin was transformed into 4-phenylcoumarin derivatives bearing C-H, C-S, C-N, and C-C bonds at 3-position

  一锅中以中等收率顺利获得各种4-芳基-3-溴香豆素，方法是在CuCl的存在下用二芳基碘鎓三氟甲磺酸和K2CO3处理3-芳基-2-丙酸，然后与四丁基溴化铵（TBAB）和Na2S2O8反应。将获得的3-溴-4-苯基香豆素转化为在3-位带有CH，CS，CN和CC键的4-苯基香豆素衍生物。
• Palladium-Catalyzed Decarboxylative Cross-Coupling of 1,3,4-Oxa­diazoles with Alkynoic Acids: A Simple Route for the Preparation of 2-Alkynylated 1,3,4-Oxadiazoles
  作者：Ch. Reddy、L. Reddy、P. Reddy

  DOI：10.1055/s-0036-1588115

  日期：——

  4-oxadiazole derivatives have been synthesized by the decarboxylative cross-coupling of alk-2-ynoic acids with 2-(het)aryl-1,3,4-oxadiazoles, employing palladium(II) chloride as the catalyst and silver(I) oxide as an oxidant with 1,3-bis(diphenylphosphanyl)propane as a ligand. Products were formed in high yields with no byproduct. For the first time 2-alk-1-ynyl-5-(het)aryl-1,3,4-oxadiazole derivatives have

  摘要 首次通过烷-2-炔酸与2-（杂）芳基的脱羧交叉偶联合成了2-alk-1-炔基-5-（杂）芳基-1,3,4-恶二唑衍生物-1,3,4-恶二唑，采用氯化钯（II）作为催化剂，氧化银（I）作为氧化剂，以1,3-双（二苯基膦基）丙烷为配体。产物以高收率形成，没有副产物。 首次通过烷-2-炔酸与2-（杂）芳基的脱羧交叉偶联合成了2-alk-1-炔基-5-（杂）芳基-1,3,4-恶二唑衍生物-1,3,4-恶二唑，采用氯化钯（II）作为催化剂，氧化银（I）作为氧化剂，以1,3-双（二苯基膦基）丙烷为配体。产物以高收率形成，没有副产物。
• Metal‐Free Oxidative Decarboxylative Heteroannulation of Alkynyl Carboxylic Acids with Sulfinates and <i>tert</i> ‐Butyl Nitrite toward 2,2‐Disulfonyl‐2 <i>H</i> ‐Azirines
  作者：Xin Yue、Xingyi He、Yan‐Chen Wu、Ming Hu、Shuang Wu、Ye‐Xiang Xie、Jin‐Heng Li

  DOI：10.1002/cctc.201902400

  日期：2020.5.20

  A new TBAF (tetrabutylammonium fluoride)‐promoted TBHP (tert‐butyl hydroperoxide)‐mediated decarboxylative heteroannulation cascades of alkynyl carboxylic acids with sodium sulfinates and TBN (tert‐butyl nitrite) has been developed for producing 2,2‐disulfonyl‐2H‐azirines under metal‐free conditions. By employing readily available tert‐butyl nitrite as the nitrogen source, the method enable the formation

  一个新的TBAF（四丁基氟化铵）促进的TBHP（叔丁基过氧化氢）介导的脱羧杂环化级联炔羧酸与亚磺酸的钠和TBN（叔丁基亚硝酸盐）已经用于生产2,2-二磺酰-2被开发ħ不含金属的偶氮基。通过使用现成的亚硝酸叔丁酯作为氮源，该方法能够通过脱羧，磺酰赖氨酸和氮掺入环合级联反应在单个反应中形成四个新的化学键，并提供了高效获得二磺酰化2 H-叠氮基的途径。
• N-Heterocyclic Carbene-Catalyzed <i>in situ</i> Activation of Alkynyl Acids for C−S Bond Formation: Access to Imidazo[2,1-<i>b</i> ][1,3]thiazinones
  作者：Kewen Sun、Shiyi Jin、Jindong Zhu、Xinmiao Zhang、Maoyu Gao、Wanqi Zhang、Tao Lu、Ding Du

  DOI：10.1002/adsc.201800857

  日期：2018.12.3

  Alkynyl acids are first utilized as alkynyl acylazolium precursors through an in situ activation strategy for the efficient construction of carbon‐sulfur bond in a formal [3+3] annulation. This protocol offers a direct and rapid pathway for the synthesis of imidazo[2,1‐b][1,3]thiazinone skeleton, a useful heterocyclic class frequently found in many bioactive compounds. This reaction also has the advantages

  炔酸首先通过原位活化策略用作炔基酰基la唑前体，以便在正式​​的[3 + 3]环空中有效构建碳硫键。该方案为合成咪唑并[2,1– b ] [1,3]噻嗪酮骨架提供了直接而快速的途径，该骨架是在许多生物活性化合物中经常发现的有用的杂环类。该反应还具有可扩展性，易于获得的材料以及在露天中易于操作的优点。
• Decarboxylative Tribromination for the Selective Synthesis of Tribromomethyl Ketone and Tribromovinyl Derivatives
  作者：Aravindan Jayaraman、Eunjeong Cho、Jimin Kim、Sunwoo Lee

  DOI：10.1002/adsc.201800851

  日期：2018.10.18

  Tribromomethyl ketone and tribromovinyl derivatives were selectively prepared from the decarboxylative tribromination. The reaction between propiolic acid derivatives and dibromoisocyanuric acid (DBCA)/H2O afforded predominantly a tribromomethyl ketone derivative in the presence of AgOAc (10 mol%). When the same reaction was conducted with 2,2,6,6‐tetramethyl‐1‐piperidinyloxy (TEMPO) instead of AgOAc

  由脱羧三溴化作用选择性地制备三溴甲基酮和三溴乙烯基衍生物。在AgOAc（10mol％）存在下，丙酸衍生物与二溴异氰尿酸（DBCA）/ H 2 O之间的反应主要得到三溴甲基酮衍生物。当用2,2,6,6-四甲基-1-哌啶基氧基（TEMPO）代替AgOAc进行相同的反应时，仅以高收率形成了三溴乙烯基衍生物。发现乙炔基溴是中间体。