2-diazo-3-(3-hexynyl)cyclohexanone | 124583-43-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-diazo-3-(3-hexynyl)cyclohexanone
• 英文别名: 2-Diazo-3-hex-3-ynylcyclohexan-1-one
• CAS: 124583-43-3
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: KFBNGVOFCQZWPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  19.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-diazo-3-(3-hexynyl)cyclohexanone 在 rhodium⁽²⁺⁾ 作用下， 以85%的产率得到2-ethyl-2a,7a-furo-3,4,4a,5,6,7-hexahydroindene
  参考文献：
  名称：

  Generation of vinylcarbenes by the intramolecular addition of .alpha.-diazo ketones to acetylenes

  摘要：

  DOI：

  10.1021/jo00289a006
• 作为产物：
  描述：

  1-溴-3-己炔 在 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-diazo-3-(3-hexynyl)cyclohexanone
  参考文献：
  名称：

  Rhodium(II)-catalyzed cyclization of 2-alkynyl 2-diazo-3-oxobutanoates as a method for synthesizing substituted furans

  摘要：

  A series of 2-alkynyl 2-diazo-3-oxobutanoates, when treated with a catalytic quantity of rhodium(II) acetate, were found to produce furo[3,4-c]furans in good yield. The reaction proceeds by addition of a rhodium-stabilized carbenoid onto the acetylenic pi-bond to give a vinyl carbenoid which subsequently cyclizes onto the neighboring carbonyl group to produce the furan ring. In a similar manner, indeno[1,2-c]furans were produced from 2-butynyl 2-diazoarylacetates. Compounds substituted with methyl groups on the propargylic carbon atom cyclized at a slower rate. This rate diminution is attributed to the fact that the unsubstituted propargyl group can more easily achieve the required conformation for cyclization. C-H insertion was found to compete with furan formation when an alkyl group was attached to the keto functionality of the starting diazo acetoacetate. Diazo alkynyl sulfones undergo a novel oxygen transfer reaction when treated with rhodium(II) acetate at 80-degrees-C. The cyclized product is formed by sulfone oxygen attack onto the vinyl carbenoid producing a dipolar species which subsequently collapses to give the butenolide sulfoxide.

  DOI：

  10.1021/jo00053a009

文献信息

• PADWA, ALBERT;CHIACCHIO, UGO;GARREAU, YVES;KASSIR, JAMAL M.;KRUMPE, KEITH+, J. ORG. CHEM., 90,(1990) N, C. 414-416
  作者：PADWA, ALBERT、CHIACCHIO, UGO、GARREAU, YVES、KASSIR, JAMAL M.、KRUMPE, KEITH+

  DOI：——

  日期：——