三甲基(辛-1-烯基)硅烷 | 65644-33-9

• 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
• 中文名称: 三甲基(辛-1-烯基)硅烷
• 英文名称: 1-(trimethylsilyl)-1-octene
• 英文别名: Silane, trimethyl-1-octenyl-；trimethyl(oct-1-enyl)silane
• CAS: 65644-33-9
• 化学式: C₁₁H₂₄Si
• 分子量: 184.397
• InChiKey: DWVPGZOBZDSBQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  三甲基(辛-1-烯基)硅烷 在 间氯过氧苯甲酸 作用下， 以71%的产率得到1-trimethylsilyl-1,2-epoxyoctane
  参考文献：
  名称：

  A New Method of Deuterium Incorporation to TMS-Epoxyalcohol Using Sodium Methylsulfinylmethylide-d5 (NaDMSO-d5)

  摘要：

  A reaction of 1-TMS-1,2-epoxyoctan-3-ol with NaDMSO-d(5) (Na+ CD3S(O)CD2-), prepared in situ from DMSO-d(6) and NaH, afforded non-1-ene-1,1-d(2)-3,4-diol. Both the anti and syn isomers showed similar reactivity and the stereochemistry was preserved. alpha-Ethoxyethyl ether of the epoxy alcohol was converted to the corresponding mono-ethoxyethyl ether of the 1-ene-3,4-diol. Hydroboration and hydrogenation of the corresponding TBS ethers afforded compounds with the "CH2CD2OH" and "CH2CD2H" groups, respectively.

  DOI：

  10.3987/com-18-s(t)32
• 作为产物：
  描述：

  trimethyl(oct-1-yn-1-yl)silane 在 二异丁基氢化铝 作用下， 以 正己烷 为溶剂， 以90%的产率得到三甲基(辛-1-烯基)硅烷
  参考文献：
  名称：

  金属促进环化。18. (.omega.-halo-1-alkenyl) 金属衍生物的新型环烷基化反应。合成范围和机制

  摘要：

  环化 d'(ω-halogenoalcene-1yl) M et d'([ω-halogeno trimethylsilyl-1] alcene-1yl) M 环烯（M = 铝、锌、锆、硅）

  DOI：

  10.1021/ja00224a025

文献信息

• Synthesis of γ,δ,-unsaturated α-amino acids from allylsilanes and glycidyl cation equivalents
  作者：Hendrik H. Mooiweer、Henk Hiemstra、W.Nico Speckamp

  DOI：10.1016/s0040-4020(01)89098-0

  日期：——

  The synthesis of a series of γ,δ-unsaturated N-protected α-amino acid methyl esters from the coupling of different allylsilanes and glycidyl cation equivalents 6 and 7 is described. Reactions with methoxyglycine derivative 6 are induced with BF3·OEt2; in the case of chloroglycine derivative 7 SnCl4 is used as Lewis acid. Reactions are fully regioselective, but show low stereoselectivity. The conversion

  描述了由不同的烯丙基硅烷和缩水甘油基阳离子当量6和7的偶联合成一系列的γ，δ-不饱和的N-保护的α-氨基酸甲基酯。BF 3 ·OEt 2诱导与甲氧基甘氨酸衍生物6的反应。在氯甘氨酸衍生物7的情况下，将SnCl 4用作路易斯酸。反应是完全区域选择性的，但显示出低的立体选择性。在两种情况下描述了反应产物向未保护的α-氨基酸的转化。
• Electrochemical synthesis of organosilicon compounds
  作者：Junichi Yoshida、Katsuhiko Muraki、Hirokatsu Funahashi、Nariyoshi Kawabata

  DOI：10.1021/jo00371a016

  日期：1986.10
• Hexafluoroisopropanol as a Unique Solvent for Stereoselective Iododesilylation of Vinylsilanes
  作者：Elizabeth A. Ilardi、Craig E. Stivala、Armen Zakarian

  DOI：10.1021/ol800341z

  日期：2008.5.1

  Stereoselective preparation of iodoalkenes from vinylsilanes is described. 1,1,1,3,3,3-HexafluoroisopropanoI serves as a unique solvent that ensures high yields and stereoselectivities in the lododesilylation of a variety of functionalized substrates.
• Metal promoted cyclization. 18. Novel cyclialkylation reactions of (.omega.-halo-1-alkenyl)metal derivatives. Synthetic scope and mechanism
  作者：Eiichi. Negishi、Larry D. Boardman、Hiroyuki. Sawada、Vahid. Bagheri、A. Timothy. Stoll、James M. Tour、Cynthia L. Rand

  DOI：10.1021/ja00224a025

  日期：1988.8

  Cyclisation d'(ω-halogenoalcene-1yl) M et d'([ω-halogeno trimethylsilyl-1] alcene-1yl) M en cyclenes (M=aluminium, zinc, zirconium, ou silicium)

  环化 d'(ω-halogenoalcene-1yl) M et d'([ω-halogeno trimethylsilyl-1] alcene-1yl) M 环烯（M = 铝、锌、锆、硅）
• A New Method of Deuterium Incorporation to TMS-Epoxyalcohol Using Sodium Methylsulfinylmethylide-d5 (NaDMSO-d5)
  作者：Yuichi Kobayashi、Yutaro Nanba、Shuhei Tanabe

  DOI：10.3987/com-18-s(t)32

  日期：——

  A reaction of 1-TMS-1,2-epoxyoctan-3-ol with NaDMSO-d(5) (Na+ CD3S(O)CD2-), prepared in situ from DMSO-d(6) and NaH, afforded non-1-ene-1,1-d(2)-3,4-diol. Both the anti and syn isomers showed similar reactivity and the stereochemistry was preserved. alpha-Ethoxyethyl ether of the epoxy alcohol was converted to the corresponding mono-ethoxyethyl ether of the 1-ene-3,4-diol. Hydroboration and hydrogenation of the corresponding TBS ethers afforded compounds with the "CH2CD2OH" and "CH2CD2H" groups, respectively.