1,10-Dioxaspiro[4.5]decan-2-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,10-Dioxaspiro[4.5]decan-2-ol
• 英文别名: 1,10-dioxaspiro[4.5]decan-2-ol
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: OOQAASMKWDJIRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1,10-Dioxaspiro[4.5]decan-2-ol 在 吡啶 、 4-二甲氨基吡啶 、 溴化锡 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 2-(3-methyl-2-oxobutyl)-1,6-dioxaspiro[4.5]decane
  参考文献：
  名称：

  Progress in the Synthesis of the Lituarines:  Stereocontrol in Sequential C−C Bond Formation on a Spirobutenolide Template

  摘要：

  [GRAPHICS]We describe elaboration of a tricyclic spirobutenolide corresponding to the C(7-18) tricyclic substructure common to lituarines A-C. Conjugate addition, to install the C(16) methyl, is followed by construction of the crucial C(18-19) bond by silyl enol ether addition to the derived spiroacetal C(18)-O oxonium ion. Esterification with a C(1-6) acid, and selective ozonolysis to release the C(23) carbonyl, complete the assembly of all the carbons present in the lituarine macrocyclic core.

  DOI：

  10.1021/ol0520018
• 作为产物：
  描述：

  1,6-dioxaspiro[4.5]decan-2-one 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1,10-Dioxaspiro[4.5]decan-2-ol
  参考文献：
  名称：

  Progress in the Synthesis of the Lituarines:  Stereocontrol in Sequential C−C Bond Formation on a Spirobutenolide Template

  摘要：

  [GRAPHICS]We describe elaboration of a tricyclic spirobutenolide corresponding to the C(7-18) tricyclic substructure common to lituarines A-C. Conjugate addition, to install the C(16) methyl, is followed by construction of the crucial C(18-19) bond by silyl enol ether addition to the derived spiroacetal C(18)-O oxonium ion. Esterification with a C(1-6) acid, and selective ozonolysis to release the C(23) carbonyl, complete the assembly of all the carbons present in the lituarine macrocyclic core.

  DOI：

  10.1021/ol0520018

文献信息

• Progress in the Synthesis of the Lituarines:  Stereocontrol in Sequential C−C Bond Formation on a Spirobutenolide Template
  作者：Jeremy Robertson、Jonathan W. P. Dallimore

  DOI：10.1021/ol0520018

  日期：2005.10.1

  [GRAPHICS]We describe elaboration of a tricyclic spirobutenolide corresponding to the C(7-18) tricyclic substructure common to lituarines A-C. Conjugate addition, to install the C(16) methyl, is followed by construction of the crucial C(18-19) bond by silyl enol ether addition to the derived spiroacetal C(18)-O oxonium ion. Esterification with a C(1-6) acid, and selective ozonolysis to release the C(23) carbonyl, complete the assembly of all the carbons present in the lituarine macrocyclic core.