1,7-二氧杂螺[5.5]十一碳-4-烯 | 113297-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,7-二氧杂螺[5.5]十一碳-4-烯
• 英文名称: 1,7-dioxaspiro<5.5>undec-4-ene
• 英文别名: (+/-)-1,7-dioxaspiro[5.5]undec-4-ene；1,7-dioxa-spiro[5.5]undec-4-ene；1,7-Dioxaspiro[5.5]undec-4-ene
• CAS: 113297-14-6
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: SNYOYCMJYVTWEA-UHFFFAOYSA-N

物化性质

• 沸点：
  231.3±40.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  1,7-二氧杂螺[5.5]十一碳-4-烯 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 以54%的产率得到3-bromo-1,7-dioxaspiro<5.5>undec-4-ene
  参考文献：
  名称：

  Allylic oxidation of unsaturated spiroketals.

  摘要：

  Allylic bromination of the bicyclic spiroketals (4a-c) gave predominantly the axial bromides (6), (9) and (12) which underwent S(N)2 displacement to the equatorial alcohols (7), (11) and (14) respectively using KO2/18-crown-6 in THF/DMSO (10:1).

  DOI：

  10.1016/s0040-4039(00)88531-7
• 作为产物：
  描述：

  2-ethynyltetrahydropyran 在 叔丁基锂 、 溶剂黄146 作用下， 生成 1,7-二氧杂螺[5.5]十一碳-4-烯
  参考文献：
  名称：

  A synthesis of 1,6-dioxaspiro[4.5]dec-3-enes.

  摘要：

  DOI：

  10.1016/s0040-4039(00)95551-5

文献信息

• Gold(I)-, Palladium(II)-, Platinum(II)-, and Mercury(II)-Catalysed Spirocyclization of 1,3-Enynediols: Reaction Scope
  作者：Alexander Zhdanko、Martin E. Maier

  DOI：10.1002/ejoc.201402029

  日期：2014.6

  spirocyclization of different 1,3-enynediols was investigated. The reaction was only efficient for the synthesis of [5,6]-spiroacetals. In this case, the reaction was characterized by almost quantitative yields, short reaction times, and low catalyst loadings (0.5–1 %). When the synthesis of [6,6]-spiroacetals was attempted, the reaction suffered from poor regioselectivity and a higher propensity of the

  研究了不同 1,3-烯炔二醇的螺环化。该反应仅对[5,6]-螺缩醛的合成有效。在这种情况下，该反应的特点是收率几乎是定量的、反应时间短和催化剂负载量低（0.5-1%）。当尝试合成 [6,6]-螺缩醛时，该反应的区域选择性较差，中间体二烯醇醚在酸性条件下更容易分解，因此不再可行。但是可以在较温和的条件下以区域异构体的混合物形式干净地生成二烯醇醚。这种反应效率的显着差异是由于不稳定的二烯醇醚环化得更快，得到 [5,6]-螺缩醛而不是得到 [6,6]-螺缩醛。在这项研究中，
• Allenol Ether Intermediates in the Synthesis of 1,7-Dioxaspiro[5.5]undec-4-enes and 1,6-Dioxaspiro[4.5]dec-3-enes
  作者：Philip Kocieński、Richard Whitby

  DOI：10.1055/s-1991-26640

  日期：——

  Sequential dialkylation of methoxyallene via the corresponding lithium derivatives gives 1,3-dialkylated methoxyallenes which undergo acid-catalysed ring closure to 1,7-dioxaspiro[5.5]undec-4-enes. Similarly, cyclic allenol ethers (2-vinylidenetetrahydropyrans) generated by rearrangement of 2-alkynyltetrahydropyrans cyclise on treatment with acid to give 1, 6-dioxaspiro[4.5]dec-3-enes.

  通过相应的锂衍生物对甲氧基阿伦烯进行序列二烷基化，得到的1,3-二烷基化甲氧基阿伦烯在酸性催化下发生环合反应，生成1,7-二氧杂螺[5.5]十一碳-4-烯。类似地，由2-炔基四氢吡喃重排生成的环状丙三烯醇醚（2-乙烯基四氢吡喃）在酸性处理下发生环合反应，生成1,6-二氧杂螺[4.5]癸-3-烯。
• A new synthesis of 1,7-dioxaspiro[5.5]undec-4-enes via metallated allenol ethers. A formal synthesis of talaromycins A and B
  作者：Richard Whitby、Philip Kocieński

  DOI：10.1039/c39870000906

  日期：——

  acid-catalysed ring closure to 1,7-dioxaspiro[5.5]undec-4-enes; by this route (6S*,9S*)-9-ethyl-1,7-dioxaspiro [5.5]undec-4-ene (15b) has been prepared which has previously been converted into talaromycins A and B.

  经由相应的锂衍生物对甲氧基丙二烯进行顺序二烷基化，得到1,3-二烷基化的甲氧基丙二烯，其经酸催化的闭环反应成1,7-二氧杂螺并[5.5]十一烷基-4-烯；通过这种途径，已经制备了（6 S *，9 S *）-9-乙基-1,7-二恶唑螺[5.5]十一碳-4-烯（15b），其先前已被转化为他洛霉素A和B。
• Palladium mediated spiroketal synthesis: application to pheromone synthesis
  作者：Jeremy C. Conway、Peter Quayle、Andrew C. Regan、Christopher J. Urch

  DOI：10.1016/j.tet.2005.09.055

  日期：2005.12

  Stereospecific Stille coupling reactions of 2-metallo-dihydropyrans with Z-vinyl iodo alcohols and subsequent cyclisation provides rapid access to 1,7-dioxaspiro[5.5]undecane family of spiroketals.

  2-金属二氢吡喃与Z-乙烯基碘醇的立体特异性Stille偶联反应及随后的环化作用可快速获得1,7-二氧杂螺[5.5]十一烷螺环家族。
• A Highly Efficient Access to Spiroketals, Mono-unsaturated Spiroketals, and Furans: Hg(II)-Catalyzed Cyclization of Alkyne Diols and Triols
  作者：Kontham Ravindar、Maddi Sridhar Reddy、Pierre Deslongchamps

  DOI：10.1021/ol201102x

  日期：2011.6.17

  Hg(II) salts are identified as highly efficient catalysts for the versatile construction of spiroketals from alkyne diols in aqueous conditions. Monounsaturated spiroketals and furans were accessed with equal ease when propargylic triols (or propargylic diols) were subjected to similar conditions. Even the semiprotected alkyne diols gave the corresponding spiroketals with the same ease in a cascade manner. The reactions are Instant and high yielding at ambient temperatures. Regioselectivity issues are well addressed.