1,1-diallyl-N,N-diethylsilanamine | 864498-91-9

• 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: 1,1-diallyl-N,N-diethylsilanamine
• 英文别名: diallyl-N,N-diethylsilanamine；diallyl-diethylaminosilane
• CAS: 864498-91-9
• 化学式: C₁₀H₂₁NSi
• 分子量: 183.369
• InChiKey: SDYDXFKZETYDQC-UHFFFAOYSA-N

物化性质

• 沸点：
  198.9±29.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  12.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,1-diallyl-N,N-diethylsilanamine 在 acetylacetonatodicarbonylrhodium(l) 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 21.0h， 生成 benzyl 2-[(2R,6S)-6-[(2S)-3-[(2S,3aS,4R,5R)-4-methyl-2,7-bis(prop-2-enyl)-3,3a,4,5-tetrahydro-2H-oxasilolo[2,3-b]oxasilol-5-yl]-2-phenylmethoxypropyl]oxan-2-yl]-2-methylpropanoate
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of (+)-SCH 351448

  摘要：

  An efficient and stereocontrolled total synthesis of (+)-SCH 351448, a novel activator of low-density lipoprotein receptor promoter, has been achieved with a longest linear sequence of 21 steps. Key steps include applications of the recently developed asymmetric allyl- and crotylsilane reagents and a new protodesilylative version of the tandem silylformylation/allyisilylation reaction, which provides an efficient synthesis of 1,5-syn-diols.

  DOI：

  10.1021/ol0515006
• 作为产物：
  描述：

  二乙胺 、 烯丙基溴化镁 在 三氯硅烷 作用下， 以 乙醚 为溶剂， 反应 2.67h， 以63%的产率得到1,1-diallyl-N,N-diethylsilanamine
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of (+)-SCH 351448

  摘要：

  An efficient and stereocontrolled total synthesis of (+)-SCH 351448, a novel activator of low-density lipoprotein receptor promoter, has been achieved with a longest linear sequence of 21 steps. Key steps include applications of the recently developed asymmetric allyl- and crotylsilane reagents and a new protodesilylative version of the tandem silylformylation/allyisilylation reaction, which provides an efficient synthesis of 1,5-syn-diols.

  DOI：

  10.1021/ol0515006

文献信息

• Tandem Silylformylation−Crotylsilylation/Tamao Oxidation of Internal Alkynes: A Remarkable Example of Generating Complexity from Simplicity
  作者：Jared T. Spletstoser、Michael J. Zacuto、James L. Leighton

  DOI：10.1021/ol802489w

  日期：2008.12.18

  The rhodium-catalyzed tandem silylformylation-crotylsilylation reaction has been extended to include internal alkynes. Tamao oxidation of the initial product leads to the production of a substituted enol, which undergoes highly diastereoselective tautomerization. The resulting one-pot procedure fashions three new stereocenters, a ketone, and a terminal alkene from a butenyl group, a propynyl group

  铑催化的串联甲硅烷基甲酰化-巴豆基甲硅烷基化反应已扩展到包括内部炔烃。初始产物的 Tamao 氧化导致取代的烯醇的产生，该烯醇经历高度非对映选择性互变异构化。由此产生的一锅法由丁烯基、丙炔基、甲硅烷基氢化物、H2O2 和 CO 形成三个新的立体中心、一个酮和一个末端烯烃。