trimethyl-[4-[(3Z,5Z)-3-methyl-8-trimethylsilylocta-3,5-dien-1,7-diynyl]phenyl]silane | 210583-68-9

• 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: trimethyl-[4-[(3Z,5Z)-3-methyl-8-trimethylsilylocta-3,5-dien-1,7-diynyl]phenyl]silane
• CAS: 210583-68-9
• 化学式: C₂₁H₂₈Si₂
• 分子量: 336.624
• InChiKey: UNUKITUTQNQWRS-FFJFLNDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  trimethyl-[4-[(3Z,5Z)-3-methyl-8-trimethylsilylocta-3,5-dien-1,7-diynyl]phenyl]silane 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 14.0h， 以54%的产率得到(5Z,11Z)-1,10-Dimethyl-11,12-bis-(4-trimethylsilanyl-phenyl)-dibenzo[a,e]cyclooctene
  参考文献：
  名称：

  A Facile Cascade Synthesis of 5,6-Diaryldibenzo[a,e]cyclooctenes from (Z,Z)-1-Aryl-3,5-octadiene-1,7-diynes

  摘要：

  Sequential treatment of (Z)-3-methyI-2-penten-4-ynal (10) with the allenylborane 2 and 8-aminoethanol furnished II. The use of II for cross-coupling with aryl iodides followed by the KH-induced syn elimination of the coupled adducts 13 provided easy access to a variety of dienediynes 14 for subsequent conversions to dibenzo[a,e]cyclooctenes (sym-dibenzocyclooctatetraenes) 17. By cross-coupling with 1,2- and 1,4-diiodobenzene, it was possible to obtain 19 and 25 having two dienediynyl moieties. It was anticipated that the oligomers 21 and 26 containing multiple dibenzo[a,e]cyclooctenyl units could thus be synthesized. The H-1 NMR spectrum of 32 having three dibenzo[a,e]cyclooctenyl units indicates the presence of three diastereomers 32a-c in a random statistical distribution of 2:1:1. Similarly, the H-1 NMR spectrum of 33 having two dibenzo[a,e]cyclooctenyl units exhibits signals that support the presence of two diastereomers 33a and 33b ina 1:1 ratio.

  DOI：

  10.1021/jo9802473
• 作为产物：
  描述：

  3-(tert-butyldimethylsilyl)-1-trimethylsilylprop-1-yne 在 9-METHOXY-9-BORABICYCLO[3.3.1]NONANE 、 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 三氟化硼乙醚 、 potassium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 trimethyl-[4-[(3Z,5Z)-3-methyl-8-trimethylsilylocta-3,5-dien-1,7-diynyl]phenyl]silane
  参考文献：
  名称：

  A Facile Cascade Synthesis of 5,6-Diaryldibenzo[a,e]cyclooctenes from (Z,Z)-1-Aryl-3,5-octadiene-1,7-diynes

  摘要：

  Sequential treatment of (Z)-3-methyI-2-penten-4-ynal (10) with the allenylborane 2 and 8-aminoethanol furnished II. The use of II for cross-coupling with aryl iodides followed by the KH-induced syn elimination of the coupled adducts 13 provided easy access to a variety of dienediynes 14 for subsequent conversions to dibenzo[a,e]cyclooctenes (sym-dibenzocyclooctatetraenes) 17. By cross-coupling with 1,2- and 1,4-diiodobenzene, it was possible to obtain 19 and 25 having two dienediynyl moieties. It was anticipated that the oligomers 21 and 26 containing multiple dibenzo[a,e]cyclooctenyl units could thus be synthesized. The H-1 NMR spectrum of 32 having three dibenzo[a,e]cyclooctenyl units indicates the presence of three diastereomers 32a-c in a random statistical distribution of 2:1:1. Similarly, the H-1 NMR spectrum of 33 having two dibenzo[a,e]cyclooctenyl units exhibits signals that support the presence of two diastereomers 33a and 33b ina 1:1 ratio.

  DOI：

  10.1021/jo9802473

文献信息

• A Facile Cascade Synthesis of 5,6-Diaryldibenzo[<i>a</i>,<i>e</i>]cyclooctenes from (<i>Z</i>,<i>Z</i>)-1-Aryl-3,5-octadiene-1,7-diynes
  作者：Kung K. Wang、Chongsheng Shi、Jeffrey L. Petersen

  DOI：10.1021/jo9802473

  日期：1998.6.1

  Sequential treatment of (Z)-3-methyI-2-penten-4-ynal (10) with the allenylborane 2 and 8-aminoethanol furnished II. The use of II for cross-coupling with aryl iodides followed by the KH-induced syn elimination of the coupled adducts 13 provided easy access to a variety of dienediynes 14 for subsequent conversions to dibenzo[a,e]cyclooctenes (sym-dibenzocyclooctatetraenes) 17. By cross-coupling with 1,2- and 1,4-diiodobenzene, it was possible to obtain 19 and 25 having two dienediynyl moieties. It was anticipated that the oligomers 21 and 26 containing multiple dibenzo[a,e]cyclooctenyl units could thus be synthesized. The H-1 NMR spectrum of 32 having three dibenzo[a,e]cyclooctenyl units indicates the presence of three diastereomers 32a-c in a random statistical distribution of 2:1:1. Similarly, the H-1 NMR spectrum of 33 having two dibenzo[a,e]cyclooctenyl units exhibits signals that support the presence of two diastereomers 33a and 33b ina 1:1 ratio.