3,3-diethynylpenta-1,4-diyne | 148549-29-5

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 3,3-diethynylpenta-1,4-diyne
• 英文别名: tetraethynylmethane；Tetraethynyl methane
• CAS: 148549-29-5
• 化学式: C₉H₄
• 分子量: 112.131
• InChiKey: JVMGUYOVBKXTJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  碘苯 、 3,3-diethynylpenta-1,4-diyne 在 copper(l) iodide 、 四(三苯基膦)钯 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 3,3-bis(2-phenylethynyl)-1,5-diphenylpent-1,4-diyne
  参考文献：
  名称：

  Preparation and Some Subsequent Transformations of Tetraethynylmethane

  摘要：

  Tetraethynylmethane (1) was synthesized in 10 steps and 33% overall yield from bis[(trimethysilyl)ethynyl] ketone. This route features (1) construction of the critical central quaternary center via the agency of a [3,3] sigmatropic shift and (2) installation of the fourth acetylene unit in a very sterically demanding environment. Alternative routes and model systems which were more informative than productive are also discussed. Finally, transition metal-mediated coupling of the rather unstable 1 (and derivatives) with unsaturated partners furnished a variety of relatively stable polylalkynylated species which could be manipulated without event.

  DOI：

  10.1021/ja00099a020
• 作为产物：
  描述：

  3,3-bis<(trimethylsilyl)ethynyl>-5-(trimethylsilyl)pent-1,4-diyne 在 甲醇 、 potassium carbonate 作用下， 反应 0.25h， 以85%的产率得到3,3-diethynylpenta-1,4-diyne
  参考文献：
  名称：

  Preparation and Some Subsequent Transformations of Tetraethynylmethane

  摘要：

  Tetraethynylmethane (1) was synthesized in 10 steps and 33% overall yield from bis[(trimethysilyl)ethynyl] ketone. This route features (1) construction of the critical central quaternary center via the agency of a [3,3] sigmatropic shift and (2) installation of the fourth acetylene unit in a very sterically demanding environment. Alternative routes and model systems which were more informative than productive are also discussed. Finally, transition metal-mediated coupling of the rather unstable 1 (and derivatives) with unsaturated partners furnished a variety of relatively stable polylalkynylated species which could be manipulated without event.

  DOI：

  10.1021/ja00099a020

文献信息

• A 3D Organically Synthesized Porous Carbon Material for Lithium-Ion Batteries
  作者：Ziqiang Zhao、Saikat Das、Guolong Xing、Pierre Fayon、Patrick Heasman、Michael Jay、Steven Bailey、Colin Lambert、Hiroki Yamada、Toru Wakihara、Abbie Trewin、Teng Ben、Shilun Qiu、Valentin Valtchev

  DOI：10.1002/anie.201805924

  日期：2018.9.10

  We report the first organically synthesized sp–sp3 hybridized porous carbon, OSPC‐1. This new carbon shows electron conductivity, high porosity, the highest uptake of lithium ions of any carbon material to‐date, and the ability to inhibit dangerous lithium dendrite formation. The new carbon exhibits exceptional potential as anode material for lithium‐ion batteries (LIBs) with high capacity, excellent

  我们报告了第一个有机合成的sp–sp 3杂化多孔碳OSPC-1。这种新碳显示出电子导电性，高孔隙率，迄今为止所有碳材料中锂离子的最高吸收率以及抑制危险的锂枝晶形成的能力。这种新型碳材料具有高容量，出色的倍率性能，长循环寿命以及改善安全性能的潜力，具有作为锂离子电池（LIB）负极材料的巨大潜力。
• Tetraethynylmethane
  作者：Ken S. Feldman、Carolyn M. Kraebel、Masood Parvez

  DOI：10.1021/ja00062a089

  日期：1993.5
• Feldman Ken S., Weinreb Carolyn K., Youngs Wiley J., Bradshaw John D., J. Amer. Chem. Soc, 116 (1994) N 20, S 9019-9026
  作者：Feldman Ken S., Weinreb Carolyn K., Youngs Wiley J., Bradshaw John D.

  DOI：——

  日期：——
• Preparation and Some Subsequent Transformations of Tetraethynylmethane
  作者：Ken S. Feldman、Carolyn K. Weinreb、Wiley J. Youngs、John D. Bradshaw

  DOI：10.1021/ja00099a020

  日期：1994.10

  Tetraethynylmethane (1) was synthesized in 10 steps and 33% overall yield from bis[(trimethysilyl)ethynyl] ketone. This route features (1) construction of the critical central quaternary center via the agency of a [3,3] sigmatropic shift and (2) installation of the fourth acetylene unit in a very sterically demanding environment. Alternative routes and model systems which were more informative than productive are also discussed. Finally, transition metal-mediated coupling of the rather unstable 1 (and derivatives) with unsaturated partners furnished a variety of relatively stable polylalkynylated species which could be manipulated without event.