1,5-二甲基-4-己烯基4-甲基苯磺酸酯1,5-二甲基-4-己烯基4-甲基苯磺酸酯 | 4582-61-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,5-二甲基-4-己烯基4-甲基苯磺酸酯1,5-二甲基-4-己烯基4-甲基苯磺酸酯
• 英文名称: tosylate de methyl-2-ol-6-heptene-2
• 英文别名: 2-<(tolylsulfonyl)oxy>-6-methyl-5-heptene；6-Methyl-2--hept-5-en；6-Methyl-5-hepten-2-p-toluolsulfonat；1,5-dimethylhex-4-enyl 4-methylbenzenesulfonate；1,5-Dimethyl-4-hexenyl 4-methylbenzenesulfonate；6-methylhept-5-en-2-yl 4-methylbenzenesulfonate
• CAS: 4582-61-0
• 化学式: C₁₅H₂₂O₃S
• 分子量: 282.404
• InChiKey: YQUVVXHOSZUKBR-UHFFFAOYSA-N

物化性质

• 沸点：
  393.9±21.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,5-二甲基-4-己烯基4-甲基苯磺酸酯1,5-二甲基-4-己烯基4-甲基苯磺酸酯 在 copper(l) iodide 、 碳酸氢钠 、 间氯过氧苯甲酸 、 sodium iodide 、 锌 作用下， 以 乙醇 、 氯仿 、 水 、 丙酮 为溶剂， 生成 4,8-dimethyl-7,8-epoxynonanenitrile
  参考文献：
  名称：

  Sonochemistry of epoxyalkylhalides in the presence of a zinc–copper couple

  摘要：

  在乙醇水溶液中超声处理下，锌-铜对会诱导环氧烷基基团与缺电子烯烃发生共轭加成，从而获得合成上有用的产率，前提是两个可还原官能团相距足够远。已发现3,4-环氧烷基卤化物可形成环丙烷加合物。

  DOI：

  10.1039/c39920000798
• 作为产物：
  描述：

  6-甲基-5-庚烯-2-酮 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 1,5-二甲基-4-己烯基4-甲基苯磺酸酯1,5-二甲基-4-己烯基4-甲基苯磺酸酯
  参考文献：
  名称：

  Total synthesis of (.+-.)-cedrol and (.+-.)-cedrene via an intramolecular Diels-Alder reaction

  摘要：

  DOI：

  10.1021/jo00404a025

文献信息

• A new synthon for the regiospecific γ-alkylation of 2-cyclohexenones. Application to the synthesis of zingiberenol and oxygenated bicycle[3.3.1] nonanes
  作者：Leo A. Paquette、William A. Kinney

  DOI：10.1016/s0040-4039(00)86766-0

  日期：——

  The regiospecific γ-alkylation of γ-sulfonycyclohexone ketals is described and applied to variuos synthetic objectives.

  描述了γ-磺酰基环己酮缩酮的区域特异性γ-烷基化，并将其应用于多种合成目的。
• Knouzi, Noureddine; Vaultier, Michel; Carrie, Robert, Bulletin de la Societe Chimique de France, 1985, # 5, p. 815 - 819
  作者：Knouzi, Noureddine、Vaultier, Michel、Carrie, Robert

  DOI：——

  日期：——
• Ring Closure Reactions of Substituted 4-Pentenyl-1-oxy Radicals. The Stereoselective Synthesis of Functionalized Disubstituted Tetrahydrofurans
  作者：Jens Hartung、Fabienne Gallou

  DOI：10.1021/jo00126a021

  日期：1995.10

  N-(Alkyloxy)pyridine-2( VT)-thiones 3 and benzenesulfenic acid O-esters 5 have been synthesized from substituted 4-pentenols 1 or the derived tosylates. Compounds 3 and 5 are efficient sources of free alkoxy radicals 6 which undergo synthetically useful fast ring closure reactions 6 --> 8 [k(exo) = (2 +/- 1) x 10(8) s(-1) to (6 +/- 2) x 10(9) s(-1) (T = 30 +/- 0.2 degrees C)]. Tetrahydrofurfuryl radicals 8 can be trapped with, e.g., hydrogen or chlorine atom donors to afford either trans- or cis-disubstituted tetrahydrofurans 10 or 12 depending on the substitution pattern of the 4-pentenyloxy radical. Substituted tetrahydropyrans 11 or 13 are formed in the minor 6-endo-trig cyclization. According to the data of competition kinetics, the observed stereoselectivities in free alkoxy radical cyclizations arise from steric interactions between the substituents in the transition state of the ring closure reactions. Alkyl substituents cause small differences in the measured relative rate constants of B-exo cyclizations which are reminiscent of the data obtained from the rearrangements of alkyl-substituted 5-hexenyl radicals. Likewise, a stereochemical model for oxygen radical cyclization is proposed where the pentenyloxy chain adopts a six-membered, chairlike transition state with the alkyl substituents preferentially situated in the pseudoequatorial positions leading to 2,5-trans-, 2,4-cis-, and 2,3-trans-substituted tetrahydrofurfuryl radicals 8 as the major intermediates.
• WO2008/45543
  申请人：——

  公开号：——

  公开（公告）日：——
• Regiocontrolled synthesis of mono-, di-, and trisubstituted cyclohexenones by cycloaddition of vinyl sulfones to 1-methoxy-3-[(trimethylsilyl)oxy]-1,3-butadienes. Conversion of alkenes into effective dienophilic reagents
  作者：William A. Kinney、Gary D. Crouse、Leo A. Paquette

  DOI：10.1021/jo00173a040

  日期：1983.12