7-tert-Butyl-5,7-dimethyl-6,8-dioxa-bicyclo[3.2.1]octane | 142169-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 7-tert-Butyl-5,7-dimethyl-6,8-dioxa-bicyclo[3.2.1]octane
• 英文别名: 7-Tert-butyl-5,7-dimethyl-6,8-dioxabicyclo[3.2.1]octane
• CAS: 142169-39-9
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: OALYABQUQMCLDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-tert-Butyl-5,7-dimethyl-6,8-dioxa-bicyclo[3.2.1]octane 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以67%的产率得到7,8,8-trimethylnonane-2,6-dione
  参考文献：
  名称：

  TRANSKETALIZATION AND REGIOSELECTIVE ALDOL CONDENSATION IN BICYCLIC KETAL SYSTEM

  摘要：

  A convenient one-pot transketalization reaction of bicyclic ketal compound was obtained by using NaI-AcCl in ketone, and a regioselective aldol condensation of bicyclic ketal compound was also made by using NaI-TMSCl in acetonitrile.

  DOI：

  10.1081/scc-100103320

文献信息

• A facile one-pot synthesis of 2,3,6-trisubstituted pyridine derivatives from bicyclic ketal by using TMSOMs (5 equiv.)-BF3·Et2O (1 equiv.)
  作者：Jong-Gab Jun、Tae Hee Ha、Dae-Whang Kim

  DOI：10.1016/0040-4039(94)88032-8

  日期：1994.2

  TMSOMs (5 equiv.)-BF3·Et2O (1 equiv.) complex was studied for the selective cleavage of bicyclic ketal and a useful method was found for the preparation of 2,3,6-trisubstituted pyridine in good yield. The bicyclic ketal was cleaved and rearranged to 1,5-diketone which was then reacted with nitrile affording pyridine as a sole product in one-flask.

  研究了TMSOMs（5当量）-BF 3 ·Et 2 O（1当量）配合物对双环缩酮的选择性裂解，发现了一种有用的方法以高收率制备2,3,6-三取代的吡啶。将双环缩酮裂解并重排为1，5-二酮，然后使其与腈反应，从而在一个烧瓶中提供吡啶作为唯一产物。
• Selective, one-pot synthesis of 2,3,6-trisubstituted pyridine and 2-cyclohexen-1-one derivatives from bicyclic ketals
  作者：Jong-Gab Jun、Tae Hee Ha

  DOI：10.1002/jhet.5570340151

  日期：1997.1

  Boron difluoromethanesulfonate, prepared from 5 equivalents of trimethylsilyl methanesulfonate and 1 equivalent of boron trifluoride etherate, has proved to be an active Lewis acid catalyst for the one-pot transformation reaction of bicyclic ketals in the 6,8-dioxabicyclo[3.2.1]octane series to 2,3,6-trisubstituted pyridine or 2-cyclohexen-1-one selectively, depending on conditions. A 1,5-diketone

  由5当量的甲磺酸三甲基甲硅烷基酯和1当量的三氟化硼乙醚组成的二氟甲磺酸硼已被证明是在6,8-二氧杂双环[3.2.1]辛烷中一锅转化双环缩酮的有效路易斯酸催化剂。取决于条件，选择性地将其串联成2,3,6-三取代的吡啶或2-环己烯-1-酮。1，5-二酮是两种产物的反应中间体。通过使用腈作为溶剂或试剂选择性地形成吡啶，但是在二氯甲烷中代替腈制备了环己烯酮。
• A novel one step preparation of 2,6-disubstituted pyridines from bicyclic ketals
  作者：Jong-Gab Jun、Hyun Shun Shin

  DOI：10.1016/s0040-4039(00)61321-7

  日期：1992.8

  6,8-Dioxabicyclo[3.2.1loctanes(1) were readily converted to 2,6 disubstituted pyridine derivatives(2) in one step by treatment with AlCl3,-NH2OH·HCl/AcOH.

  通过用AlCl 3，-NH 2 OH·HCl / AcOH处理，一步就很容易将6,8-二氧杂双环[3.2.1loctanes（1）转化为2,6-二取代的吡啶衍生物（2）。
• Jun, Jong-Gab; Shin, Hyun Shun; Kim, Sung Hoon, Journal of the Chemical Society. Perkin transactions I, 1993, # 15, p. 1815 - 1818
  作者：Jun, Jong-Gab、Shin, Hyun Shun、Kim, Sung Hoon

  DOI：——

  日期：——
• Jun Jong-Gab, Ha Tae Hee, Kim Dae-Whang, Tetrahedron Lett, 35 (1994) N 8, S 1235-1238
  作者：Jun Jong-Gab, Ha Tae Hee, Kim Dae-Whang

  DOI：——

  日期：——