3-triethylgermyl-2-propyn-1-al | 63247-76-7

• 分子结构分类: 有机化合物 - 乙炔化物 - 金属乙炔化物
• 英文名称: 3-triethylgermyl-2-propyn-1-al
• 英文别名: (triethylgermyl)propynal；3-(triethylgermyl)propynal；2-Propynal, 3-(triethylgermyl)-；3-triethylgermylprop-2-ynal
• CAS: 63247-76-7
• 化学式: C₉H₁₆GeO
• 分子量: 212.815
• InChiKey: LMYKQHYETLICSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  81-82 °C(Press: 6 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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-triethylgermyl-2-propyn-1-al 在 苯胺 作用下， 以 乙醚 为溶剂， 以87%的产率得到N-phenyl-3-triethylgermylprop-2-yn-1-imine
  参考文献：
  名称：

  Yakovleva, E. V.; Sokolov, V. V.; Stadnichuk, M. D., Journal of general chemistry of the USSR, 1991, vol. 61, p. 2107 - 2111

  摘要：

  DOI：

文献信息

• Key influence of the nature of the substituent in the propynal molecule on the outcome of its reaction with vicinal di(N-hydroxyamine)
  作者：E. V. Tretyakov、G. V. Romanenko、D. V. Stass、A. V. Mareev、A. S. Medvedeva、V. I. Ovcharenkoa

  DOI：10.1007/s11172-008-0094-8

  日期：2008.3

  The reaction of propynals X-C≡C-CHO, where X = Alk or Ar, with 2,3-di(N-hydroxyamino)-2,3-dimethylbutane gives exclusively 1-X-2-(1-hydroxy-4,4,5,5-tetramethylimidazolidin-2-ylidene)ethanones. In the case of X = Me3Si, the reaction affords 2-(2-trimethylsilylethynyl)-4,4,5,5-tetramethylimidazolidine-1,3-diol. The reaction of propynal containing X = Et3Ge yields both types of the products. The resulting imidazolidine-1,3-diol can be quantitatively isomerized to imidazolidin-2-ylideneethanone, oxidized to 2-[2-(triethylgermyl)ethynyl]-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl, or transformed into ethynyl-substituted nitronyl nitroxide.

  丙炔醛X-C≡C-CHO（其中X = 烷基或芳基）与2,3-二(N-羟基氨基)-2,3-二甲基丁烷反应，仅生成1-X-2-(1-羟基-4,4,5,5-四甲基咪唑啉-2-亚基)乙酮。在X = 三甲基硅基的情况下，反应得到2-(2-三甲基硅基乙炔基)-4,4,5,5-四甲基咪唑啉-1,3-二醇。含有X = 三乙基锗的丙炔醛反应生成两种类型的产物。所得的咪唑啉-1,3-二醇可以定量异构化为咪唑啉-2-亚基乙酮，氧化为2-[2-(三乙基锗基)乙炔基]-4,4,5,5-四甲基-4,5-二氢-1H-咪唑-3-氧化物-1-氧基，或转化为乙炔基取代的氮氧自由基。
• Synthesis of oxazolines and oxazoles by the reaction of propynals with tosylmethyl isocyanide
  作者：Victoria G. Elshina、Vladimir V. Novokshonov、Ekaterina A. Verochkina、Igor A. Ushakov、Igor B. Rosentsveig、Nadezhda V. Vchislo

  DOI：10.1016/j.mencom.2019.11.015

  日期：2019.11

  The reaction of 3-(trimethylsilyl)propynal, 3-(triethylgermyl) propynal or 3-phenylpropynal with tosylmethyl isocyanide affords new 5-alkynyl-4-tosyl-2-oxazolines and/or 5-alkynyl-1,3-oxazoles.

  3-（三甲基甲硅烷基）丙炔，3-（三乙基锗基）丙炔或3-苯基丙炔与甲苯磺酰基甲基异氰化物的反应提供了新的5-炔基-4-甲苯基-2-恶唑啉和/或5-炔基-1,3-恶唑。
• One-pot three-component green synthesis of [1H-(1,2,3-triazol-5-yl)methylidene] heterocycles based on element-substituted propynals
  作者：M. M. Demina、A. S. Medvedeva、T. L. H. Nguyen、T. D. Vu、L. I. Larina

  DOI：10.1007/s11172-017-2010-6

  日期：2017.12

  The one-pot three-component synthesis of polyfunctional bis-heterocyclic triazoles, namely, previously unknown 1H-1,2,3-triazolylmethylidenepyrimidines and -1,3-dioxanes, was performed for the first time in moderate or high yields starting from element-substituted propynals, trimethylsilyl azide, and heterocyclic CH-acids at room temperature in aqueous medium.

  首次以中等或高收率从元素开始进行了多功能双杂环三唑的一锅三组分合成，即以前未知的1H-1,2,3-三唑基亚甲基嘧啶和-1,3-二恶烷。 -取代的丙炔醛、三甲基甲硅烷基叠氮化物和杂环 CH-酸在室温下在水性介质中。
• The aldol-type condensation of methyl diazoacetate with 3-organyl-silyl and -germyl propynals and their carbon analogues
  作者：O.I. Margorskaya、A.S. Medvedeva、M.M. Demina、I.D. Kalikhman、M.G. Voronkov

  DOI：10.1016/0022-328x(89)88071-4

  日期：1989.10

  addition of methyl diazoacetate (I) to the carbonyl group of the substituted propyn-1-als RCCCHO (II) (R = alkyl, Alk3Si, Et3Ge) to give the corresponding methyl esters of 2-diazo-3-hydroxy-4-pentyn carboxylic acid RCCCH(OH)C(N2)COOMe (III) have been found. Shielding of the triple bond in II by the bulky R group or complexation with dicobalt octacarbonyl, the presence of strong electron acceptor

  未催化，选择性地将重氮乙酸甲酯（I）加至取代的丙炔基1-丙二醛RCCCHO（II）（R =烷基，Alk 3 Si，Et 3 Ge）的羰基上的最佳条件已经发现2-重氮-3-羟基-4-戊炔羧酸RC ＝ CCH（OH）C（N 2）COOMe（III）的相应甲酯。通过庞大的R基团屏蔽二代中的三键，或与二钴八羰基二钴络合，在二代的3位上存在强电子受体（4-NO 2 C 6 H 4），并且溶剂的极性低在选择性羟醛缩合中。γ-羟基丙醛R 1 R 2的反应具有重氮乙酸甲酯的C（OH）＝ CCHO也通过醛醇型加成而进行，并且涉及两个丙炔分子，形成二炔基重氮四环（VIII）。将重氮乙酸甲酯的β加成到三烷基甲硅烷基或-锗基丙炔中的三键上，得到异构的甲酰基吡唑IV和V.IV的4位上含Si或Ge的取代基的存在会促进它们的二聚为三环半胱氨酸，VI。
• The reaction of methyl diazoacetate with 4,4-dimethyl-2-pentyn-1-al and related compounds
  作者：A.S. Medvedeva、M.M. Demina、A.I. Borisova、O.I. Margorskaya、I.D. Kalikhman、E.I. Brodskaya、N.S. Vyazankin

  DOI：10.1016/s0022-328x(00)81949-x

  日期：1982.5

  Methyl 2-diazo-3-hydroxy-6,6-dimethyl-4-heptynoate was prepared by treating 4,4-dimethyl-2-pentyn-1-al with methyl diazoacetate at room temperature in the absence of catalysts. In the case of related aldehydes, RCCCHO (R = n-Bu, Me3Si, Et3Si, Et3Ge), this unusual reaction is partially or completely suppressed by a competing 1,3-cycloaddition process. The latter leads to a mixture of isomeric 3- and

  通过在不存在催化剂的情况下在室温下用重氮乙酸甲酯处理4，4-二甲基-2-戊炔-1-α，来制备2-重氮-3-羟基-6，6-二甲基-4-庚酸甲酯。在相关的醛RCCCHO（R = n-Bu，Me 3 Si，Et 3 Si，Et 3 Ge）的情况下，这种异常反应被竞争的1,3-环加成过程部分或完全抑制。后者导致异构体3-和4-甲酰基吡唑的混合物，其中一种被丙二聚化而形成三环半缩醛。