(Z)-9-[(tetrahydro-2H-pyran-2-yl)oxy]-6-octen-2-yn-1-ol | 782485-34-1

• 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: (Z)-9-[(tetrahydro-2H-pyran-2-yl)oxy]-6-octen-2-yn-1-ol
• 英文别名: (Z)-9-(oxan-2-yloxy)non-6-en-2-yn-1-ol
• CAS: 782485-34-1
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: JXHGDWBGIQBLRX-HYXAFXHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-9-[(tetrahydro-2H-pyran-2-yl)oxy]-6-octen-2-yn-1-ol 在 (NH₄)6Mo₇*4H₂O 、 potassium tert-butylate 、 双氧水 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 叔丁醇 为溶剂， 反应 4.33h， 生成 2-methyl-3-(phenylsulfonyl)-4,5,8,9-tetrahydrooxonin
  参考文献：
  名称：

  Base-Catalyzed Endo-Mode Cyclization of Allenes:  Easy Preparation of Five- to Nine-Membered Oxacycles

  摘要：

  A reliable and efficient procedure for constructing five- to eight-membered oxacycles has been developed. Allenes with both a phosphoryl group and a suitable delta-hydroxyalkyl side chain at the Cl-position underwent an endo mode ring-closing reaction to give five- to seven-membered oxacycles. Changing the phosphoryl group to a phosphono functionality facilitated the preparation of eight-membered congeners. Introduction of a cis double bond to the alkyl side chain of the starting allenes made possible the easy formation of medium-sized oxacycles, such as the dihydrooxocin and tetrahydrooxonin frameworks, regardless of the electron-withdrawing group (POPh2, PO(OEt)(2), SOPh, and SO2Ph) at the C-1-position.

  DOI：

  10.1021/jo0488614
• 作为产物：
  描述：

  (5Z)-8-[(tetrahydro-2H-pyran-2-yl)oxy]-5-octen-1-ynyltrimethylsilane 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 5.0h， 生成 (Z)-9-[(tetrahydro-2H-pyran-2-yl)oxy]-6-octen-2-yn-1-ol
  参考文献：
  名称：

  Base-Catalyzed Endo-Mode Cyclization of Allenes:  Easy Preparation of Five- to Nine-Membered Oxacycles

  摘要：

  A reliable and efficient procedure for constructing five- to eight-membered oxacycles has been developed. Allenes with both a phosphoryl group and a suitable delta-hydroxyalkyl side chain at the Cl-position underwent an endo mode ring-closing reaction to give five- to seven-membered oxacycles. Changing the phosphoryl group to a phosphono functionality facilitated the preparation of eight-membered congeners. Introduction of a cis double bond to the alkyl side chain of the starting allenes made possible the easy formation of medium-sized oxacycles, such as the dihydrooxocin and tetrahydrooxonin frameworks, regardless of the electron-withdrawing group (POPh2, PO(OEt)(2), SOPh, and SO2Ph) at the C-1-position.

  DOI：

  10.1021/jo0488614

文献信息

• Base-Catalyzed Endo-Mode Cyclization of Allenes:  Easy Preparation of Five- to Nine-Membered Oxacycles
  作者：Chisato Mukai、Masaru Ohta、Haruhisa Yamashita、Shinji Kitagaki

  DOI：10.1021/jo0488614

  日期：2004.10.1

  A reliable and efficient procedure for constructing five- to eight-membered oxacycles has been developed. Allenes with both a phosphoryl group and a suitable delta-hydroxyalkyl side chain at the Cl-position underwent an endo mode ring-closing reaction to give five- to seven-membered oxacycles. Changing the phosphoryl group to a phosphono functionality facilitated the preparation of eight-membered congeners. Introduction of a cis double bond to the alkyl side chain of the starting allenes made possible the easy formation of medium-sized oxacycles, such as the dihydrooxocin and tetrahydrooxonin frameworks, regardless of the electron-withdrawing group (POPh2, PO(OEt)(2), SOPh, and SO2Ph) at the C-1-position.