non-4-yne-1,9-diol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: non-4-yne-1,9-diol
• 英文别名: 4-nonyne-1,9-diol
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: GXZYOWKUROMAMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  non-4-yne-1,9-diol 在 mercuric triflate 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以92%的产率得到1,7-二氧螺环-[5,5]十一烷
  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
• 作为产物：
  描述：

  2-(4-戊炔氧基)四氢-2H-吡喃 在 正丁基锂 、 四丁基氟化铵 、 对甲苯磺酸 、 4-羟甲基-3-甲氧基苯氧基乙酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 21.75h， 生成 non-4-yne-1,9-diol
  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

• Metal-Catalyzed Regioselective Oxy-Functionalization of Internal Alkynes:  An Entry into Ketones, Acetals, and Spiroketals
  作者：Bo Liu、Jef K. De Brabander

  DOI：10.1021/ol0619819

  日期：2006.10.1

  text] Platinum(II) and an unusual cationic gold(I) complex were identified as mild catalysts for the room temperature cycloisomerization or tandem hydroalkoxylation/acetal formation of unactivated internal alkynols. Under the appropriate conditions, 5-endo, 5-exo, 6-endo, and 6-exo cycloisomerization modes are all available.

  [反应：见正文]铂（II）和一种不寻常的阳离子金（I）络合物被确定为室温环异构化或未活化内部炔醇的串联加氢烷氧基化/缩醛形成的温和催化剂。在适当的条件下，可以使用5-endo，5-exo，6-endo和6-exo环异构化模式。
• 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。
• UTIMOTO, KIITIRO, PURE AND APPL. CHEM., 1983, 55, N 11, 1845-1852
  作者：UTIMOTO, KIITIRO

  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.