dimethyl 2-(2,3-butadienyl)-2-(3,5-dimethoxybenzyl)malonate | 1013916-83-0

• 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: dimethyl 2-(2,3-butadienyl)-2-(3,5-dimethoxybenzyl)malonate
• 英文别名: 1,3-Dimethyl 2-(2,3-butadien-1-yl)-2-[(3,5-dimethoxyphenyl)methyl]propanedioate
• CAS: 1013916-83-0
• 化学式: C₁₈H₂₂O₆
• 分子量: 334.369
• InChiKey: JSDSXBSMHXNYOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(2,3-butadienyl)-2-(3,5-dimethoxybenzyl)malonate 在 2,6-di-tert-butylpyridine 作用下， 以 not given 为溶剂， 生成 [(gold(I))(PPh3)C(CH2)CH(CH2C(COOMe)2CH2)C6H2(OMe)2]
  参考文献：
  名称：

  Weber, Dieter; Tarselli, Michael A.; Gagne, Michel R., Angewandte Chemie - International Edition, 2009, vol. 48, p. 5733 - 5736

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二甲氧基溴苄 、 dimethyl 2,3-butadienylmalonate 在 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以64%的产率得到dimethyl 2-(2,3-butadienyl)-2-(3,5-dimethoxybenzyl)malonate
  参考文献：
  名称：

  Gold(I)-Catalyzed Intramolecular Hydroarylation of Allenes

  摘要：

  Gold(I) complexes react with 4-allenyl arenes in an exo fashion to furnish vinyl-substituted benzocycles. Phosphite gold(I) monocations were found to be optimal, and the catalyst was tolerant of ethers, esters, and pyrroles. Reactions proceeded in unpurified solvent at room temperature.

  DOI：

  10.1021/jo7024948

文献信息

• σ–π-Diauration as an alternative binding mode for digold intermediates in gold(<scp>i</scp>) catalysis
  作者：Dieter Weber、Michel R. Gagné

  DOI：10.1039/c2sc21281a

  日期：——

  While investigating the gold(I)-catalyzed intramolecular hydroarylation of allenes, the structure of a digold-vinyl intermediate was verified. Instead of the previously proposed geminally diaurated binding mode for the digold when L = PPh3, an alternative σ–π-diauration mode was observed with the bulkier ligand L = P(o-Tol)3. Reactivity studies indicate the σ–π-mode has a disproportionate effect on protonolysis reactivity.

  在研究金（I）催化下的烯烃分子内氢化反应时，验证了二金-乙烯基中间体的结构。当L = PPh3时，二金不是采用先前提出的双键二价结合模式，而是观察到了另一种更笨重的配体L = P(o-Tol)3的Β-二价结合模式。反应性研究表明Β-模式对质子解离反应性有不成比例的影响。
• Dinuclear Gold−Silver Resting States May Explain Silver Effects in Gold(I)-Catalysis
  作者：Dieter Weber、Michel R. Gagné

  DOI：10.1021/ol902116b

  日期：2009.11.5

  The resting state of the gold(I)-catalyzed hydroarylation of 1 changes In the presence of Ag+, with silver free catalysts resting at the dinuclear gold structure 5 and Ag+ containing solutions resting at a heteronuclear species like 6. Adventitious Ag+ (typically from LAuCl activation) can therefore intercept key organogold intermediates and effect the catalysis even when it does not effect the reaction in Au free control experiments.
• Gold(I)-Catalyzed Intramolecular Hydroarylation of Allenes
  作者：Michael A. Tarselli、Michel R. Gagné

  DOI：10.1021/jo7024948

  日期：2008.3.1

  Gold(I) complexes react with 4-allenyl arenes in an exo fashion to furnish vinyl-substituted benzocycles. Phosphite gold(I) monocations were found to be optimal, and the catalyst was tolerant of ethers, esters, and pyrroles. Reactions proceeded in unpurified solvent at room temperature.
• Weber, Dieter; Tarselli, Michael A.; Gagne, Michel R., Angewandte Chemie - International Edition, 2009, vol. 48, p. 5733 - 5736
  作者：Weber, Dieter、Tarselli, Michael A.、Gagne, Michel R.

  DOI：——

  日期：——