nona-2,7-diynedial | 283604-94-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: nona-2,7-diynedial
• 英文别名: 2,7-nonadiynedial；Nona-2,7-diin-1,9-dial
• CAS: 283604-94-4
• 化学式: C₉H₈O₂
• 分子量: 148.161
• InChiKey: AZBCVFPBGPAOKK-UHFFFAOYSA-N

物化性质

• 沸点：
  314.6±25.0 °C(predicted)
• 密度：
  1.070±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  nona-2,7-diynedial 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 9-oxo-2,7-decadiynal
  参考文献：
  名称：

  Synthesis and Cycloaromatization of a Cyclic Enyne−Allene Prodrug

  摘要：

  A simple and stable cyclic enediynone (4) has been synthesized using an intramolecular Nozaki-Hiyama-Kishi cyclization as the key step. Reaction with a thiolate nucleophile led to rapid cycloaromatization of 4. Trapping experiments using 1,4-cyclohexadiene support the intermediacy of an aromatic diradical in the cycloaromatization.

  DOI：

  10.1021/jo034278w
• 作为产物：
  描述：

  1,6-庚二炔 、 N,N-二甲基甲酰胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.33h， 以61%的产率得到nona-2,7-diynedial
  参考文献：
  名称：

  Synthesis and Cycloaromatization of a Cyclic Enyne−Allene Prodrug

  摘要：

  A simple and stable cyclic enediynone (4) has been synthesized using an intramolecular Nozaki-Hiyama-Kishi cyclization as the key step. Reaction with a thiolate nucleophile led to rapid cycloaromatization of 4. Trapping experiments using 1,4-cyclohexadiene support the intermediacy of an aromatic diradical in the cycloaromatization.

  DOI：

  10.1021/jo034278w

文献信息

• Chelation-Controlled Intermolecular Alkene and Alkyne Hydroacylation: The Utility of β-Thioacetal Aldehydes
  作者：Michael C. Willis、Helen E. Randell-Sly、Robert L. Woodward、Gordon S. Currie

  DOI：10.1021/ol050638l

  日期：2005.5.1

  beta-Thioacetal-substituted aldehydes, which are conveniently prepared from the corresponding ynals, can be combined with a range of alkynes or electron-poor alkenes to deliver intermolecular hydroacylation adducts. The reactions employ [Rh(dppe)]ClO4 as a catalyst and are proposed to proceed via a chelated rhodium acyl intermediate. The thioacetal-containing products can be deprotected to the corresponding ketones or reduced to alkanes in good yields.
• Synthesis and Cycloaromatization of a Cyclic Enyne−Allene Prodrug
  作者：Tefsit Bekele、Steven R. Brunette、Mark A. Lipton

  DOI：10.1021/jo034278w

  日期：2003.10.1

  A simple and stable cyclic enediynone (4) has been synthesized using an intramolecular Nozaki-Hiyama-Kishi cyclization as the key step. Reaction with a thiolate nucleophile led to rapid cycloaromatization of 4. Trapping experiments using 1,4-cyclohexadiene support the intermediacy of an aromatic diradical in the cycloaromatization.