9-(5,5-dimethoxypentyl)-9-borabicyclo[3.3.1]nonane | 913361-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: 9-(5,5-dimethoxypentyl)-9-borabicyclo[3.3.1]nonane
• CAS: 913361-73-6
• 化学式: C₁₅H₂₉BO₂
• 分子量: 252.205
• InChiKey: USHNBGAQUKWYTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  9-(5,5-dimethoxypentyl)-9-borabicyclo[3.3.1]nonane 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 吡啶 、 2,4,6-三甲基吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 2,6-bis(dimethylamino)pyridine 、 四氯化锡 作用下， 以 四氢呋喃 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 水 为溶剂， 反应 40.33h， 生成 acetic acid [1-(2-methoxycyclohexyl)-3,3-dimethylcyclopentyl]methyl ester
  参考文献：
  名称：

  Scope and Facial Selectivity of the Prins-Pinacol Synthesis of Attached Rings

  摘要：

  [GRAPHICS]Using a B-alkyl Suzuki cross-coupling as a key step, a concise and stereocontrolled synthesis of five- to eight-membered triisopropylsiloxy ethers having (2Z)-(6,6-dimethoxyhexylidene) or (2Z)-(5,5-dimethoxypentylidene) side chains was developed. Prins-pinacol reactions of these precursors promoted by SnCl4 provide bicyclic products in which 5-, 6-, or 7-membered rings are joined by a C-C single bond. Synthetically challenging attached ring systems in which both rings are chiral can be prepared in this fashion with high stereo- and enantioselectivity. Stabilizing through-space electrostatic interactions between the alpha-alkoxycarbenium ion and an axially positioned oxygen substituent are believed to play a significant role in organizing the transition structure of the Prins cyclization.

  DOI：

  10.1021/jo0522862
• 作为产物：
  描述：

  5,5-dimethoxypent-1-ene 、 9-硼双环[3.3.1]壬烷 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 9-(5,5-dimethoxypentyl)-9-borabicyclo[3.3.1]nonane
  参考文献：
  名称：

  Scope and Facial Selectivity of the Prins-Pinacol Synthesis of Attached Rings

  摘要：

  [GRAPHICS]Using a B-alkyl Suzuki cross-coupling as a key step, a concise and stereocontrolled synthesis of five- to eight-membered triisopropylsiloxy ethers having (2Z)-(6,6-dimethoxyhexylidene) or (2Z)-(5,5-dimethoxypentylidene) side chains was developed. Prins-pinacol reactions of these precursors promoted by SnCl4 provide bicyclic products in which 5-, 6-, or 7-membered rings are joined by a C-C single bond. Synthetically challenging attached ring systems in which both rings are chiral can be prepared in this fashion with high stereo- and enantioselectivity. Stabilizing through-space electrostatic interactions between the alpha-alkoxycarbenium ion and an axially positioned oxygen substituent are believed to play a significant role in organizing the transition structure of the Prins cyclization.

  DOI：

  10.1021/jo0522862