3,7-dimethyl-6,7-epoxyoctyl p-toluenesulfonate | 70200-30-5

• 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: 3,7-dimethyl-6,7-epoxyoctyl p-toluenesulfonate
• 英文别名: [5-(3,3-Dimethyloxiran-2-yl)-3-methylpentyl] 4-methylbenzenesulfonate
• CAS: 70200-30-5
• 化学式: C₁₇H₂₆O₄S
• 分子量: 326.457
• InChiKey: BVSYWZZEOXMFJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,7-dimethyl-6,7-epoxyoctyl p-toluenesulfonate 在 copper(l) iodide 、 sodium iodide 、 锌 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 生成
  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：

  (+/-)-citronellyl tosylate 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 生成 3,7-dimethyl-6,7-epoxyoctyl p-toluenesulfonate
  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

文献信息

• Practical and efficient methods for sulfonylation of alcohols using Ts(Ms)Cl/Et3N and catalytic Me3H·HCl as combined base: Promising alternative to traditional pyridine
  作者：Yoshihiro Yoshida、Yoshiko Sakakura、Naoya Aso、Shin Okada、Yoo Tanabe

  DOI：10.1016/s0040-4020(99)00002-2

  日期：1999.2

  Several alcohols were smoothly and practically tosylated by two methods A and B. Method A uses the TsCl/Et3N (1.5-2.5 equiv)/cat. Me3N . HCl (0.1-1.0 equiv) reagent. Compared with the traditional qr-solvent method, the method A has merits of its much higher reaction rate, operational simplicity, economy in the use of the amine, and circumvention of the undesirable side reaction from R-OTs to R-CL Method B uses TsCl/KOH [or Ca(OH)(2)]/cat. Et3N (0.1 equiv)/cat. Me3N . HCl (0.1 equiv) as the reagent, which will be suited for practical and large scale production for primary alcohols. On both methods A and B, a clear joint action of Et3N and Me3N . HCl catalysts was observed. H-1 NMR measurements support the proposed mechanism of the catalytic cycle. Related methanesulfonylation using Et3N and cat. Me3N . HCl in toluene solvent also successfully proceeded, wherein he clear joint action was also observed. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Sonochemistry of epoxyalkylhalides in the presence of a zinc–copper couple
  作者：Luis A. Sarandeses、Antonio MouriñO、Jean-Louis Luche

  DOI：10.1039/c39920000798

  日期：——

  Under sonication in aqueous ethanol, a zinc–copper couple induces the conjugated addition of epoxyalkyl groups to electron deficient alkenes in synthetically useful yields, provided that the two reducible functionalities are sufficiently far apart; 3,4-epoxyalkylhalides have been found to form cyclopropane adducts.

  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。