1-(diphenylmethylsilyl)hex-1-yne | 148991-48-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-(diphenylmethylsilyl)hex-1-yne
• 英文别名: hex-1-yn-1-yl(methyl)diphenylsilane；Silane, 1-hexynylmethyldiphenyl-；hex-1-ynyl-methyl-diphenylsilane
• CAS: 148991-48-4
• 化学式: C₁₉H₂₂Si
• 分子量: 278.469
• InChiKey: STSHOWAOPHHWGR-UHFFFAOYSA-N

物化性质

• 沸点：
  347.2±15.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  1-(diphenylmethylsilyl)hex-1-yne 、 alkaline earth salt of/the/ methylsulfuric acid 以 甲苯 为溶剂， 反应 2.0h， 生成 2,5-bis(diphenylmethylsilyl)-3,4-dibutylcyclopenta-2,4-dien-1-one 、 2,4-bis(diphenylmethylsilyl)-3,5-dibutylcyclopenta-2,4-dien-1-one
  参考文献：
  名称：

  Direct synthesis of cyclopentadienones by cobalt carbonyl-mediated carbonylative alkyne-alkyne coupling reaction

  摘要：

  Dicobalt carbonyl complex mediates an intermolecular carbonylative coupling reaction between alkynylsilanes, The reaction proceeds under atmospheric pressure of argon and directly provides free cyclopentadienones in high yields (up to 99%). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01175-7
• 作为产物：
  描述：

  二苯甲基硅烷 、 1-己炔 在 [Yb(η²-Ph2CNPh))(hmpa)3] 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以76%的产率得到1-(diphenylmethylsilyl)hex-1-yne
  参考文献：
  名称：

  镧系元素（II）-亚胺配合物的合成及其在碳-碳和碳-氮不饱和键转化中的应用

  摘要：

  和sa金属将芳香族酮亚胺还原，直接定量得到二价氮杂蒽环丙烷丙烷配合物1，其结构通过X射线分析表征。亚胺络合物1催化末端炔烃的脱氢甲硅烷基化，亚胺和烯烃的氢化硅烷化以及炔烃的分子间加氢磷酸化。此外，共轭二烯的脱氢双甲硅烷基化是用1实现的。

  DOI：

  10.1016/j.tet.2003.06.003

文献信息

• Inter- and Intramolecular Carbonylative Alkyne–Alkyne Coupling Reaction Mediated by Cobalt Carbonyl Complex
  作者：Takanori Shibata、Koji Yamashita、Kentaro Takagi、Toshihiro Ohta、Kenso Soai

  DOI：10.1016/s0040-4020(00)00902-9

  日期：2000.11

  Inter- and intramolecular carbonylative coupling reactions proceed between alkynes possessing diphenylallylsilyl group mediated by dicobalt carbonyl complex under argon atmosphere. This coupling reaction directly provides various mono- and bicyclic cyclopentadienones in high yields. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Dehydrogenative silation, isomerization and the control of syn- vs. anti-addition in the hydrosilation of alkynes
  作者：Chul-Ho Jun、Robert H. Crabtree

  DOI：10.1016/0022-328x(93)80236-5

  日期：1993.4

  Alkyne hydrosilation has been examined in detail for the catalysts [IrH(H2O)(bq)L2]SbF6 (L = PPh3, bq = 7,8-benzoquinolinato) and RhCl(PPh3)3. Factors that favor the normal syn- or the unusual anti-silane addition to the alkynes are examined. Two other unusual products are noted: the dehydrogenative silation product RC=CSiR3, formed by beta-elimination in a vinylmetal intermediate and allylsilane products of vinylsilane isomerization. The iridium catalyst is advantageous in that it does not give fast vinylsilane isomerization, as does RhCl(PPh3)3, so allowing formation and isolation of the thermodynamically less stable cis-, rather than the more stable trans-vinylsilane isomer RCH=CH(SiR3').
• Dehydrogenative Silylation of Terminal Alkynes Catalyzed by Ytterbium−Imine Complexes
  作者：Ken Takaki、Masanobu Kurioka、Tohru Kamata、Katsuomi Takehira、Yoshikazu Makioka、Yuzo Fujiwara

  DOI：10.1021/jo981008i

  日期：1998.12.1

  Catalytic dehydrogenative silylation of terminal alkynes with hydrosilanes has been achieved by using divalent Yb-imine complexes; The reaction with mono-, di-, and trihydrosilanes gave the corresponding alkynylsilanes in good yields. alpha,omega-Diynes were similarly silylated at both termini. Thus, oligomers were obtained from the diynes and dihydrosilanes. In addition, it has been found that the imine complexes exhibit catalytic activity for redistribution of the silyl groups of the alkynylsilanes and for Si-Si bond fission of disilanes.