endo-2-(hydroxymethyl)bicyclo<3.2.1>oct-6-ene-3-one | 129492-06-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: endo-2-(hydroxymethyl)bicyclo<3.2.1>oct-6-ene-3-one
• 英文别名: (1RS,2RS,5RS)-2-(hydroxymethyl)bicyclo[3.2.1]oct-6-en-3-one；(1R,2R,5R)-2-(hydroxymethyl)bicyclo[3.2.1]oct-6-en-3-one
• CAS: 129492-06-4
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: LGCWDFQIADEQAS-CSMHCCOUSA-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：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Triethyl-[1-(oxiran-2-yl)ethenoxy]silane 、 环戊二烯 在 三乙基硅基三氟甲磺酸酯 、 triethylamine tris(hydrogen fluoride) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (1S,2R,5S)-2-(hydroxymethyl)bicyclo[3.2.1]oct-6-en-3-one 、 endo-2-(hydroxymethyl)bicyclo<3.2.1>oct-6-ene-3-one
  参考文献：
  名称：

  Facial Selectivity and Stereospecificity in the (4 + 3) Cycloaddition of Epoxy Enol Silanes

  摘要：

  The scope of the (4 + 3) cycloaddition using epoxy enol silanes has been examined. Unhindered and nucleophilic dienes react to give the highest yields, but hindered dienes give rise to higher diastereoselectivities. Notably, the cycloaddition shows facial selectivity and stereospecificity for the stereochemistry of the epoxy enol silane.

  DOI：

  10.1021/ol102897d

文献信息

• [4 + 3]Cycloaddition reaction of some silyl enol ethers having a conjugated carbonyl functionality
  作者：Masatomi Ohno、Kohki Mori、Tatsuya Hattori、Shoji Eguchi

  DOI：10.1021/jo00312a011

  日期：1990.12
• Facial Selectivity and Stereospecificity in the (4 + 3) Cycloaddition of Epoxy Enol Silanes
  作者：Brian Lo、Pauline Chiu

  DOI：10.1021/ol102897d

  日期：2011.3.4

  The scope of the (4 + 3) cycloaddition using epoxy enol silanes has been examined. Unhindered and nucleophilic dienes react to give the highest yields, but hindered dienes give rise to higher diastereoselectivities. Notably, the cycloaddition shows facial selectivity and stereospecificity for the stereochemistry of the epoxy enol silane.