2-苯基-1,6-二氧杂-螺[4.4]壬烷 | 100612-02-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-苯基-1,6-二氧杂-螺[4.4]壬烷
• 英文名称: 2-phenyl-1,6-dioxa-spiro[4.4]nonane
• 英文别名: 2-Phenyl-1,6-dioxa-spiro[4.4]nonan；2-Phenyl-1,6-dioxaspiro[4.4]nonane
• CAS: 100612-02-0
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: DAZCRWITIXSROY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 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-(4-戊炔氧基)四氢-2H-吡喃 在 正丁基锂 、 mercuric triflate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 乙腈 为溶剂， 反应 2.17h， 生成 2-苯基-1,6-二氧杂-螺[4.4]壬烷
  参考文献：
  名称：

  A Highly Efficient Access to Spiroketals, Mono-unsaturated Spiroketals, and Furans: Hg(II)-Catalyzed Cyclization of Alkyne Diols and Triols

  摘要：

  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.

  DOI：

  10.1021/ol201102x

文献信息

• Consecutive Reactions with Sulfoximines: Straightforward Synthesis of Substituted 5,5-Spiroketals
  作者：Jean Rodriguez、Vellaisamy Sridharan、Nikolay Vologdin、Marie-Alice Virolleaud、Damien Bonne、Cyril Bressy、Gaëlle Chouraqui、Laurent Commeiras、Jean-Luc Parrain、Yoann Coquerel

  DOI：10.1055/s-0030-1260039

  日期：2011.7

  An efficient synthesis of 5,5-spiroketals (i.e., 1,6-dioxa­spiro[4.4]nonane derivatives) is described from 2-(sulfonimidoyl­methylene)tetrahydrofurans involving a consecutive epoxide opening/oxa-Michael spiroketalization sequence. This methodology was applied to the very direct synthesis of chalcogran, a beetle pheromone. sulfoximine - 5,5-spiroketals - consecutive reaction - chalcogran

  从2-（磺酰亚胺基亚甲基）四氢呋喃中描述了涉及连续的环氧化物开环/ oxa-Michael spiroketalization序列的5,5-spiroketals（即1,6-dioxaspiro [4.4]壬烷衍生物）的有效合成。该方法学被用于甲壳虫信息素chalcogran的直接合成。 亚砜亚胺-5,5-螺酮-连续反应-硫氰酸盐
• Highly efficient catalytic routes to spiroketal motifs
  作者：Selvasothi Selvaratnam、Joanne H.H. Ho、Paul B. Huleatt、Barbara A. Messerle、Christina L.L. Chai

  DOI：10.1016/j.tetlet.2008.12.075

  日期：2009.3

  The versatile and efficient synthesis of a variety of spiroketal motifs via the double intramolecular hydroalkoxylation of aliphatic and aromatic alkyne diols was achieved using simple and readily accessible Ir(I) and Rh(I) cyclooctadiene complexes as catalysts.

  通过使用简单易得的Ir（I）和Rh（I）环辛二烯络合物作为催化剂，通过脂肪族和芳香族炔二醇的双分子内加氢烷氧基化，可以实现多种螺环基序化合物的通用和高效合成。
• Til' et al., Zhurnal Obshchei Khimii, 1957, vol. 27, p. 110,111, 112; engl. Ausg. S. 125, 127
  作者：Til' et al.

  DOI：——

  日期：——
• Ponomarew et al., Doklady Akademii Nauk SSSR, 1953, vol. 93, p. 297
  作者：Ponomarew et al.

  DOI：——

  日期：——
• 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.