(Z)-7-(diethoxyphosphinyl)-2,7,8-nonatrien-1-ol | 782485-30-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (Z)-7-(diethoxyphosphinyl)-2,7,8-nonatrien-1-ol
• CAS: 782485-30-7
• 化学式: C₁₃H₂₃O₄P
• 分子量: 274.297
• InChiKey: YVLKZXNUFXOMNV-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-7-(diethoxyphosphinyl)-2,7,8-nonatrien-1-ol 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 0.33h， 以77%的产率得到1-[(1RS,2SR)-1-(diethoxyphosphinyl)-2-ethenylcyclopentyl]ethan-1-one
  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：

  6-(tert-butyldimethylsiloxy)hex-2-yn-1-ol 在 nickel diacetate 、 乙二胺 咪唑 、 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 正丁基锂 、 氢气 、 碘 、 4-甲基苯磺酸吡啶 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (Z)-7-(diethoxyphosphinyl)-2,7,8-nonatrien-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.