6-碘-1-(三甲基硅氧基)己烷 | 26306-01-4

• 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
• 中文名称: 6-碘-1-(三甲基硅氧基)己烷
• 英文名称: 6-iodo-1-(trimethylsilyloxy)hexane
• 英文别名: ((6-iodohexyl)oxy)trimethylsilane；(6-iodo-hexyloxy)-trimethylsilane；6-Iodhexanol-O-trimethylsilyl；6-Iodohexyl trimethylsilyl ether；6-iodohexoxy(trimethyl)silane
• CAS: 26306-01-4
• 化学式: C₉H₂₁IOSi
• 分子量: 300.255
• InChiKey: AFXURHYBMCAHAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-碘-1-(三甲基硅氧基)己烷 在 六甲基磷酰三胺 、 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 6-(2,5-Diphenyl-1,3-oxazol-4-yl)hexan-1-ol
  参考文献：
  名称：

  合成中的单线态氧。恶唑为羰基1,1-偶极子合成子。

  摘要：

  如7-庚醇化物，α-苄氧基δ-戊内酯和9-壬醇化物的合成所示，已将2，5-二苯基恶唑按两步顺序用作羰基1，1-偶极合成子。4-锂硫基-2，5-二苯基恶唑的烷基化，然后单线态氧氧化，产生三酰胺，该三酰胺经历环化成内酯。

  DOI：

  10.1016/s0040-4039(00)60874-2
• 作为产物：
  描述：

  6-氯-1-己醇 在 六甲基二硅氮烷 、 sodium iodide 作用下， 以 丙酮 、 苯 为溶剂， 反应 56.0h， 生成 6-碘-1-(三甲基硅氧基)己烷
  参考文献：
  名称：

  Denniff, Phillip; Whiting, Donald A., Journal of the Chemical Society. Perkin transactions I, 1980, p. 2637 - 2644

  摘要：

  DOI：

文献信息

• Cyclische Ether als Edukte zur Synthese von Schmetterlings-Pheromonen
  作者：Helmut Poleschner、Matthias Heydenreich、Dieter Martin

  DOI：10.1055/s-1991-28425

  日期：——

  Cyclic Ethers as Educts for the Synthesis of Lepidoptera Pheromones ω-Iodo(trialkylsiloxy)alkanes 2 prepared by ring opening of cyclic ethers with iodotrimethylsilane, are useful starting materials for the synthesis of pheromone components. Reaction with triphenylphosphine to give the corresponding Wittig reagent and subsequent coupling with lithium (Z)-dihex-1-enylcuprate gives (Z)-alken-1-ols 5 and 7, after deprotection, in good yields. The direct coupling of 2 with alkynes failed because of competition reactions, however, the more stable ω-iodo-1-(tert-butyldimethylsiloxy)alkanes were able to undergo C,C-coupling with alkynes. The thus formed 1-(tert-butyldimethylsiloxy)-5-decyne (13c) was hydrogenated and deprotected to give (E)-5-decen-1-ol (15c).

  环醚作为合成鳞翅目昆虫信息素的起始物 — 由环醚与碘三甲基硅烷开环制备的ω-碘(三烷基硅氧基)烷烃2，是合成信息素成分的有用起始材料。与三苯基膦反应生成相应的Wittig试剂，随后与锂(Z)-二己-1-烯基铜酸盐偶联，经过脱保护步骤后得到(Z)-烯-1-醇5和7，收率良好。直接将2与炔烃偶联失败，因为存在竞争反应，然而，更稳定的ω-碘-1-(叔丁基二甲基硅氧基)烷烃能够与炔烃进行C,C-偶联。由此形成的1-(叔丁基二甲基硅氧基)-5-癸炔(13c)经过氢化和脱保护后生成(E)-5-癸烯-1-醇(15c)。
• Unprecedented copper-mediated oxidative demethylation of propionamides via bidentate-chelation assistance
  作者：Jing-Hui Liu、Mian Cui、Xiao-Yu Lu、Zhen-Qi Zhang、Bin Xiao、Yao Fu

  DOI：10.1039/c5cc08393a

  日期：——

  The copper-mediated bidentate-chelation directing group assisted oxidative demethylation of substituted propionamides was developed for the first time.

  首次开发了铜介导的双齿螯合定向基辅助的取代丙酰胺的氧化去甲基化反应。
• Functional Group Interactions in the Mass Spectra of Trimethylsilyl Derivatives of Halo Acids and Halo Alcohols
  作者：Edward White、James McCloskey

  DOI：10.1021/jo00837a628

  日期：1970.12
• Efficient Slurry-Phase Homopolymerization of Ethylene to Branched Polyethylenes Using α-Diimine Nickel(II) Catalysts Covalently Linked to Silica Supports
  作者：Henri S. Schrekker、Vasily Kotov、Peter Preishuber-Pflugl、Peter White、Maurice Brookhart

  DOI：10.1021/ma061032v

  日期：2006.9.1

  alpha-Diimine nickel(II) complexes covalently linked to a silica support were obtained by the reaction of an amino- or hydroxy-functionalized alpha-diimine nickel complex with silica particles treated with trimethyl aluminum. These silica-supported aryl R-diimine nickel(II) precatalysts linked via an amino (1a) or hydroxy functionality (1b-c) at the p-aryl position, and precatalysts linked via one (2a) or two (2b) hydroxy functionalities in the alkyl backbone were used in slurry polymerizations of ethylene to produce branched polyethylenes. Activation of precatalysts with ethylaluminum sesquichloride was effective even at very low Al/Ni ratios of 48. Initial polymerizations, performed at 60 degrees C and 150 psig ethylene, showed excellent productivities of up to 10.8 kg PE per gram of 1b (3.0 wt % nickel loading). Low productivities at temperatures above 60 degrees C can in part be overcome by increase in ethylene pressure. For example, a productivity of 6.0 kg PE per gram of 1b (3.0 wt % nickel loading) was obtained at 80 degrees C and 700 psig ethylene. The best polymerization productivities were obtained with trimethylaluminum as a traceless silica-linker, however, tetrachlorosilane and trichloroborane are attractive alternatives. Branching densities can be controlled by choice of ortho-aryl substituents. No reactor fouling occurs with these supported catalysts.
• Singlet oxygen in synthesis. Oxazoles as carbonyl 1,1-dipole synthons.
  作者：Harry H. Wasserman、Robert W. DeSimone、Wen-Bin Ho、Keith E. McCarthy、K.Spencer Prowse、Alfred P. Spada

  DOI：10.1016/s0040-4039(00)60874-2

  日期：1992.11

  2,5-Diphenyloxazole has been utilized in a two-step sequence as a carbonyl 1,1-dipole synthon as illustrated by the synthesis of 7-heptanolide, α-benzyloxy δ-valerolactone, and 9-nonanolide. Alkylation of 4-lithio-2,5-diphenyloxazole, followed by singlet oxygen oxidation yields a triamide which undergoes cyclization to the lactone.

  如7-庚醇化物，α-苄氧基δ-戊内酯和9-壬醇化物的合成所示，已将2，5-二苯基恶唑按两步顺序用作羰基1，1-偶极合成子。4-锂硫基-2，5-二苯基恶唑的烷基化，然后单线态氧氧化，产生三酰胺，该三酰胺经历环化成内酯。