cis-7-methyl-2,9-dioxabicyclo[4.3.0]nonane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: cis-7-methyl-2,9-dioxabicyclo[4.3.0]nonane
• 英文别名: (3aR,7aS)-3-methyl-3,3a,4,5,6,7a-hexahydro-2H-furo[2,3-b]pyran
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: LBAYIVBFYVVULM-VVXQKDJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  0
• 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

• 作为产物：
  描述：

  2-allyloxy-3-bromotetrahydropyran 在 偶氮二异丁腈 、 (p-C₆F₁₃C₆H₄Se)2 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 cis-7-methyl-2,9-dioxabicyclo[4.3.0]nonane
  参考文献：
  名称：

  设计，合成，应用和回收最低限度的氟二芳基二硒化物，用于催化锡烷介导的自由基链反应

  摘要：

  描述了最低氟（52％F）二芳基二硒化物的合成。在用三丁基锡烷原位还原时，该二硒化物提供了一种氟硒醇，其有效抑制了由锡烷介导的自由基重排的范围，包括环丙基羰基的开环。描述了一种回收二硒氟的方法，该方法包括在改良的冷却的连续萃取器中连续萃取。

  DOI：

  10.1016/s0040-4020(99)00902-3

文献信息

• Design, synthesis, application and recovery of a minimally fluorous diaryl diselenide for the catalysis of stannane-mediated radical chain reactions
  作者：David Crich、Xiaolin Hao、Mathew Lucas

  DOI：10.1016/s0040-4020(99)00902-3

  日期：1999.12

  diselenide is described. On reduction in situ with tributylstannane this diselenide provides a fluorous selenol which is effective in inhibiting a range of stannane-mediated radical rearrangements, including a cyclopropylcarbinyl ring opening. A method for the recovery of the fluorous diselenide involving continuous extraction in a modified, cooled continuous extractor is described.

  描述了最低氟（52％F）二芳基二硒化物的合成。在用三丁基锡烷原位还原时，该二硒化物提供了一种氟硒醇，其有效抑制了由锡烷介导的自由基重排的范围，包括环丙基羰基的开环。描述了一种回收二硒氟的方法，该方法包括在改良的冷却的连续萃取器中连续萃取。
• Oxygenative radical cyclization with molecular oxygen
  作者：Stanislas Mayer、Jacques Prandi

  DOI：10.1016/0040-4039(96)00505-9

  日期：1996.4

  5-exo radical cyclization of olefinic iodides can be carried out under classical reductive tin hydride conditions in the presence of molecular oxygen to give high yields of cyclized alcohols.

  可以在分子氧存在下，在经典的还原性氢化锡条件下，进行烯烃碘化物的5- exo自由基环化反应，从而获得高产率的环化醇。
• Inhibition of Stannane-Mediated Radical Rearrangements by a Recoverable, Minimally Fluorous Selenol
  作者：David Crich、Xiaolin Hao、Mathew A. Lucas

  DOI：10.1021/ol990590+

  日期：1999.7.1

  [GRAPHICS]The preparation of a minimally fluorous diaryl diselenide is described. It is demonstrated that this diselenide, reduced in situ to the corresponding selenol, may be used in conjunction with stannanes to prevent a number of radical rearrangements. A 1 M solution of this selenol used in admixture with Breslow's water-soluble stannane can be used to significantly inhibit a cyclopropylcarbinyl ring opening. The combination of the fluorous selenol and the polar stannane permits recovery of the selenol by continuous fluorous extraction and isolation of a stannane-free hydrocarbon product.
• Inhibition of Rearrangements in Stannane-Mediated Radical Reduction Reactions by Catalytic Quantities of Diphenyl Diselenide. An Example of Polarity Reversal Catalysis
  作者：David Crich、Qingwei Yao

  DOI：10.1021/jo00106a018

  日期：1995.1

  The presence of only 10 mol % of PhSeH, PhSeSePh (reduced in situ to PhSeH), and, to a lesser extent, PhSH has a dramatic effect on the efficiency of stannane-mediated free radical rearrangement reactions owing to the superior hydrogen donating qualities of PhSeH and PhSH. Slow radical rearrangements can be prevented altogether, and the yields of even moderately rapid rearrangements significantly diminished. The addition of 10 mol % of PhSeSePh to stannane-mediated aryl radical cyclizations is advantageous as the initial, rapid, 5-hexenyl rearrangement is not impaired but the subsequent, slower neophyl rearrangement is effectively minimized, resulting in the formation of vastly improved 5-exo/6-endo ratios.
• Hypophosphite mediated carboncarbon bond formation: A clean approach to radical methodology
  作者：Stephen R. Graham、John A. Murphy、David Coates

  DOI：10.1016/s0040-4039(99)00117-3

  日期：1999.3

  Hypophosphorous acid (H3PO2) and its corresponding 1-ethylpiperidine salt have been used to mediate carbon-carbon bond forming radical reactions in both aqueous and organic media. The methods used avoid many of the problems associated with tributyltin hydride based methodology. (C) 1999 Elsevier Science Ltd. All rights reserved.