diethyl 2-(2-iodophenethyl)malonate | 115860-21-4

• 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: diethyl 2-(2-iodophenethyl)malonate
• 英文别名: Diethyl [2-(2-iodophenyl)ethyl]propanedioate；diethyl 2-[2-(2-iodophenyl)ethyl]propanedioate
• CAS: 115860-21-4
• 化学式: C₁₅H₁₉IO₄
• 分子量: 390.218
• InChiKey: UDEAKNVKSVVCGL-UHFFFAOYSA-N

物化性质

• 沸点：
  419.5±40.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-(2-iodophenethyl)malonate 在 sodium azide 、 二异丁基氢化铝 、 三乙胺 、 sodium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-(4-azidobutyl)-2-iodobenzene
  参考文献：
  名称：

  Facile Synthesis of [1,2,3]-Triazole-Fused Isoindolines, Tetrahydroisoquino­lines, Benzoazepines and Benzoazocines by Palladium-Copper Catalysed Heterocyclisation­

  摘要：

  An elegant method for the synthesis of 1,2,3-triazoles fused with five-, six-, seven- and eight-membered benzoheterocycles, including isoindoline, tetrahydroisoquinoline, benzoazepine and benzoazocine, has been developed via palladium-copper catalysed reactions in one-pot. The broad scope of this reaction was illustrated by effecting bis-heteroannulations, synthesis of uracil derivatives of biological interest, and employment of acetylene gas as an inexpensive substrate. The reactions are experimentally simple and utilise easily accessible substrates of different types.

  DOI：

  10.1055/s-0032-1316839
• 作为产物：
  描述：

  2-(2-碘苯基)-1-乙醇 在 咪唑 、 碘 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 diethyl 2-(2-iodophenethyl)malonate
  参考文献：
  名称：

  Generation of Medium-Ring Cycloalkynes by Ring Expansion of Vinylogous Acyl Triflates

  摘要：

  Reductive cyclization of aryl and vinyl iodides tethered to vinylogous acyl trifiates (VATS) induces a ring-expanding fragmentation to provide cyclic alkynyl ketones, including strained nine-membered cycloalkynes, in fair to excellent yield. The tandem cyclization/C-C bond-cleavage is Initiated under carefully optimized conditions by halogen metal exchange in the presence of carbonyl and vinyl triflate functionality. A modified protocol for alkylation of 1,3-cyclohexanedione is described for preparing the relevant VAT substrates.

  DOI：

  10.1021/ol2003308

文献信息

• Concise synthesis of cyclic carbonyl compounds from haloarenes using phenyl formate as the carbonyl source
  作者：Hideyuki Konishi、Hiroki Nagase、Kei Manabe

  DOI：10.1039/c4cc09413a

  日期：——

  Carbonylative cyclization of haloarenes bearing nucleophilic moieties under Pd catalysis has been developed as a general, user-friendly method for access to various cyclic carbonyl compounds.

  在钯催化下，含有亲核基团的卤代芳烃的羰基化环化已经发展成为获取各种环状羰基化合物的一种通用、用户友好的方法。

• Pd-Catalyzed Desymmetric Intramolecular <i>O</i>-Arylation Reaction: Enantioselective Synthesis of (3,4-Dihydro-2<i>H</i>-chromen-3-yl)methanols
  作者：Wenqiang Yang、Jiajie Yan、Yan Long、Shasha Zhang、Jianguang Liu、Youlin Zeng、Qian Cai

  DOI：10.1021/ol402911y

  日期：2013.12.6

  An enantioselective intramolecular O-arylation was achieved through desymmetrization with Pd-catalyzed coupling reactions. The intramolecular asymmetric aryl C-O coupling reactions of 2-(2-haloaryl)propane-1,3-diols led to the enantioselective formation of chiral (3,4-dihydro-2H-chromen-3-yl)methanols in good yields and high enantiomeric selectivity.
• Spirocyclization by Palladium-Catalyzed Domino Heck–Direct C–H Arylation Reactions: Synthesis of Spirodihydroquinolin-2-ones
  作者：Tiffany Piou、Luc Neuville、Jieping Zhu

  DOI：10.1021/ol301616w

  日期：2012.7.20

  Treatment of a DMA solution of anilide 1 with a catalytic amount of palladium acetate (0.025 equiv) and XPhos (0.05 equiv) in the presence of potassium carbonate (2.0 equiv) at 100 degrees C afforded dihydroquinolin-2-ones spiro-fused to dihydrofuranyl, indolinyl, and indanyl 2 in good to excellent yields. The reaction went through a domino sequence involving a 5-exo-trig Heck cyclization followed by an intramolecular direct C-H functionalization.
• Intramolecular arylations of soft enolates catalyzed by zerovalent palladium
  作者：Marco A. Ciufolini、Hong Bo Qi、Margaret E. Browne

  DOI：10.1021/jo00252a064

  日期：1988.8
• Generation of Medium-Ring Cycloalkynes by Ring Expansion of Vinylogous Acyl Triflates
  作者：Jumreang Tummatorn、Gregory B. Dudley

  DOI：10.1021/ol2003308

  日期：2011.3.18

  Reductive cyclization of aryl and vinyl iodides tethered to vinylogous acyl trifiates (VATS) induces a ring-expanding fragmentation to provide cyclic alkynyl ketones, including strained nine-membered cycloalkynes, in fair to excellent yield. The tandem cyclization/C-C bond-cleavage is Initiated under carefully optimized conditions by halogen metal exchange in the presence of carbonyl and vinyl triflate functionality. A modified protocol for alkylation of 1,3-cyclohexanedione is described for preparing the relevant VAT substrates.