1,1-dimethyl-2,4-diphenylsilole | 144921-38-0

• 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: 1,1-dimethyl-2,4-diphenylsilole
• 英文别名: 1,1-Dimethyl-2,4-diphenylsilole
• CAS: 144921-38-0
• 化学式: C₁₈H₁₈Si
• 分子量: 262.426
• InChiKey: VKFJBZZXUMWVHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• 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：

  1,1-dimethyl-2,4-diphenylsilole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 2-bromo-1,1-dimethyl-3,5-diphenylsilole
  参考文献：
  名称：

  Silylboranes Bearing Dialkylamino Groups on Silicon as Silylene Equivalents:  Palladium-Catalyzed Regioselective Synthesis of 2,4-Disubstituted Siloles

  摘要：

  Silylpinacolboranes bearing dialkylamino groups on the silicon atom several as synthetic equivalents of silylene in palladium-catalyzed reactions with terminal alkynes, leading to the formation of 2, 4-disubstituted siloles in high yield. It was found that the amino group on the silicon atom was critically important for the reaction; no silole products were found in reactions using silylpinacolboranes carrying aryl, chloro, or alkoxy groups on the silicon atoms. Site-selective bromination of 1,1-dimethyl-2,4-diphenylsilole followed by Migita-Kasugi-Stille coupling with (arylalkynyl)tributylstannanes gave novel Pi-conjugated siloles with good total yields.

  DOI：

  10.1021/ja073896h
• 作为产物：
  描述：

  1,1-dimethyl-2,4-diphenyl-1-silacyclopent-3-ene 在 四氯苯醌 作用下， 以 苯 为溶剂， 反应 1.0h， 以97%的产率得到1,1-dimethyl-2,4-diphenylsilole
  参考文献：
  名称：

  钯催化的亚甲硅烷-1,3-二烯 [4 + 1] 环加成反应，使用（氨基甲硅烷基）硼酸酯作为亚甲硅烷的合成等价物

  摘要：

  硅原子上带有二烷基氨基的甲硅烷基硼酸酯在钯催化剂的存在下与 1,3-二烯反应，通过有效地从甲硅烷基硼酸酯转移甲硅烷基，以高产率得到硅杂环戊 3-烯（即 2,5-二氢硅酮） 1,3-二烯的酯。[4 + 1] 环加成适用于母体 1,3-丁二烯和各种具有甲硅烷氧基、氰基和酯基团的单、二和三取代的 1,3-二烯。在与 5,7-十二二烯的任一立体异构体的反应中发生立体有择的环形成：(E,E)-二烯产生顺式产物，而在异构体 (E,Z) 的反应中观察到反式产物的选择性形成)-二烯。[4 + 1] 环加成，然后用 DDQ 或氯苯醌脱氢得到 2,4- 和 2,5- 二芳基甲硅烷。

  DOI：

  10.1021/ja907170p

文献信息

• Silylboranes Bearing Dialkylamino Groups on Silicon as Silylene Equivalents:  Palladium-Catalyzed Regioselective Synthesis of 2,4-Disubstituted Siloles
  作者：Toshimichi Ohmura、Kohei Masuda、Michinori Suginome

  DOI：10.1021/ja073896h

  日期：2008.2.6

  Silylpinacolboranes bearing dialkylamino groups on the silicon atom several as synthetic equivalents of silylene in palladium-catalyzed reactions with terminal alkynes, leading to the formation of 2, 4-disubstituted siloles in high yield. It was found that the amino group on the silicon atom was critically important for the reaction; no silole products were found in reactions using silylpinacolboranes carrying aryl, chloro, or alkoxy groups on the silicon atoms. Site-selective bromination of 1,1-dimethyl-2,4-diphenylsilole followed by Migita-Kasugi-Stille coupling with (arylalkynyl)tributylstannanes gave novel Pi-conjugated siloles with good total yields.
• Palladium-Catalyzed Silylene-1,3-Diene [4 + 1] Cycloaddition with Use of (Aminosilyl)boronic Esters as Synthetic Equivalents of Silylene
  作者：Toshimichi Ohmura、Kohei Masuda、Ichiro Takase、Michinori Suginome

  DOI：10.1021/ja907170p

  日期：2009.11.25

  3-dienes having silyloxy, cyano, and ester groups. Stereospecific ring formation took place in the reaction with either stereoisomer of 5,7-dodecadiene: the (E,E)-diene gave the cis product, whereas selective formation of the trans product was observed in the reaction of the isomeric (E,Z)-diene. The [4 + 1] cycloaddition followed by dehydrogenation with DDQ or chloranil afforded 2,4- and 2,5-diarylsiloles

  硅原子上带有二烷基氨基的甲硅烷基硼酸酯在钯催化剂的存在下与 1,3-二烯反应，通过有效地从甲硅烷基硼酸酯转移甲硅烷基，以高产率得到硅杂环戊 3-烯（即 2,5-二氢硅酮） 1,3-二烯的酯。[4 + 1] 环加成适用于母体 1,3-丁二烯和各种具有甲硅烷氧基、氰基和酯基团的单、二和三取代的 1,3-二烯。在与 5,7-十二二烯的任一立体异构体的反应中发生立体有择的环形成：(E,E)-二烯产生顺式产物，而在异构体 (E,Z) 的反应中观察到反式产物的选择性形成)-二烯。[4 + 1] 环加成，然后用 DDQ 或氯苯醌脱氢得到 2,4- 和 2,5- 二芳基甲硅烷。