dimethyl 2-(4-(4-methoxyphenyl)-2-methylenebut-3-yn-1-yl)malonate | 1262884-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: dimethyl 2-(4-(4-methoxyphenyl)-2-methylenebut-3-yn-1-yl)malonate
• 英文别名: Dimethyl 2-[4-(4-methoxyphenyl)-2-methylidenebut-3-ynyl]propanedioate；dimethyl 2-[4-(4-methoxyphenyl)-2-methylidenebut-3-ynyl]propanedioate
• CAS: 1262884-35-4
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: JICJTHITTDCBHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  炔丙基丙二酸二甲酯 、 4-乙炔基苯甲醚 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 氢碘酸 、 trisodium tris(3-sulfophenyl)phosphine 、 palladium diacetate 、 二异丙胺 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 1.0h， 生成 dimethyl 2-(4-(4-methoxyphenyl)-2-methylenebut-3-yn-1-yl)malonate
  参考文献：
  名称：

  Iridium-catalyzed hydroiodination of functionalized alkynes

  摘要：

  The efficiency of an Ir(I)/HI system has been studied. The association of hydroiodic acid with iridium has been tested in the catalytic hydroiodination of alkynes. The use of [Ir(cod)Cl](2) dimer led to clean hydroiodination reactions and afforded the corresponding vinyliodides as a mixture of derivatives, where the Markovnikov type adduct was found to be the major product (80/20 to 93/7 ratio), in good yields. The mechanism was investigated and two main pathways seemed to be involved, one based on an initial oxidative addition of HI to the Ir(I) complex and the other one based on a pi-activation of the alkyne moiety. The corresponding vinyliodides were engaged in Pd-catalyzed cross-coupling (Sonogashira and Suzuki-Miyaura) reactions under organoaqueuous conditions. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.10.052

文献信息

• Iridium-catalyzed hydroiodination of functionalized alkynes
  作者：Mehdi Ez-Zoubir、Jack A. Brown、Virginie Ratovelomanana-Vidal、Véronique Michelet

  DOI：10.1016/j.jorganchem.2010.10.052

  日期：2011.1

  The efficiency of an Ir(I)/HI system has been studied. The association of hydroiodic acid with iridium has been tested in the catalytic hydroiodination of alkynes. The use of [Ir(cod)Cl](2) dimer led to clean hydroiodination reactions and afforded the corresponding vinyliodides as a mixture of derivatives, where the Markovnikov type adduct was found to be the major product (80/20 to 93/7 ratio), in good yields. The mechanism was investigated and two main pathways seemed to be involved, one based on an initial oxidative addition of HI to the Ir(I) complex and the other one based on a pi-activation of the alkyne moiety. The corresponding vinyliodides were engaged in Pd-catalyzed cross-coupling (Sonogashira and Suzuki-Miyaura) reactions under organoaqueuous conditions. (C) 2010 Elsevier B.V. All rights reserved.