1,4-dimethyl-5,6,7,8-tetrahydro-isochromen-3-one | 111395-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 1,4-dimethyl-5,6,7,8-tetrahydro-isochromen-3-one
• 英文别名: 1,4-Dimethyl-5,6,7,8-tetrahydroisochromen-3-one
• CAS: 111395-94-9
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: GWYKRXMQASOGCN-UHFFFAOYSA-N

物化性质

• 沸点：
  341.5±11.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,8-癸二炔 、 二氧化碳 在 bis(1,5-cyclooctadiene)nickel (0) 1,3-双(2,6-二异丙基苯基)咪唑-2-烯 作用下， 以 甲苯 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以77%的产率得到1,4-dimethyl-5,6,7,8-tetrahydro-isochromen-3-one
  参考文献：
  名称：

  Efficient Nickel-Catalyzed [2 + 2 + 2] Cycloaddition of CO₂ and Diynes

  摘要：

  A mild and general route for preparing 2-pyrones from CO2 and diynes is described. Under only 1 atm of CO2, excellent yields of pyrone are obtained using catalytic amounts of Ni(COD)2 and imidazolylidene ligand, IPr. In addition, stoichiometric reactions between the isolated complex Ni(IPr)2, diynes, and CO2 suggest that the pathway involves initial reaction with CO2 as the key step.

  DOI：

  10.1021/ja027438e

文献信息

• Tsuda, Tetsuo; Sumiya, Ritsuo; Saegusa, Takeo, Synthetic Communications, 1987, vol. 17, # 2, p. 147 - 154
  作者：Tsuda, Tetsuo、Sumiya, Ritsuo、Saegusa, Takeo

  DOI：——

  日期：——
• Nickel(0)-catalyzed cycloaddition of diynes and carbon dioxide to give bicyclic .alpha.-pyrones
  作者：Tetsuo Tsuda、Shohei Morikawa、Ritsuo Sumiya、Takeo Saegusa

  DOI：10.1021/jo00249a003

  日期：1988.7
• TSUDA, TETSUO;MORIKAWA, SHOHEI;SUMIYA, RITSUO;SAEGUSA, TAKEO, J. ORG. CHEM., 53,(1988) N 14, 3140-3145
  作者：TSUDA, TETSUO、MORIKAWA, SHOHEI、SUMIYA, RITSUO、SAEGUSA, TAKEO

  DOI：——

  日期：——
• TSUDA TETSUO; SUMIYA RITSUO; SAEGUSA TAKEO, SYNTH. COMMUN., 17,(1987) N 2, 147-154
  作者：TSUDA TETSUO、 SUMIYA RITSUO、 SAEGUSA TAKEO

  DOI：——

  日期：——
• Efficient Nickel-Catalyzed [2 + 2 + 2] Cycloaddition of CO₂ and Diynes
  作者：Janis Louie、John E. Gibby、Marc V. Farnworth、Thomas N. Tekavec

  DOI：10.1021/ja027438e

  日期：2002.12.1

  A mild and general route for preparing 2-pyrones from CO2 and diynes is described. Under only 1 atm of CO2, excellent yields of pyrone are obtained using catalytic amounts of Ni(COD)2 and imidazolylidene ligand, IPr. In addition, stoichiometric reactions between the isolated complex Ni(IPr)2, diynes, and CO2 suggest that the pathway involves initial reaction with CO2 as the key step.