| 1108146-08-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• CAS: 1108146-08-2
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: AFIUXDACMLGYCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  在 Pd/C 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以97%的产率得到2-methyl-2-[2-(1-naphthyl)ethyl]cyclopentane-1,3-dione
  参考文献：
  名称：

  Pentacyclic Compounds by Samarium Diiodide‐Induced Cascade Cyclizations of Naphthyl‐Substituted 1,3‐Diones

  摘要：

  AbstractTreatment of naphthyl‐substituted cyclopentane‐1,3‐diones with the samarium diiodide‐ hexamethylphosphoramide (HMPA) complex in the presence of tert‐butyl alcohol provided the expected tetracyclic diols with steroid‐like structures. Surprisingly, reactions without the proton source led to the efficient formation of a new pentacyclic diol. In this case the toxic additive HMPA could be substituted by a combination of lithium bromide (in situ generation of samarium dibromide) and N,N‐dimethylimidazolidone. The styrene‐like alkene moiety of this product was used to prepare an ensemble of highly substituted pentacyclic steroid‐like compounds.

  DOI：

  10.1002/adsc.200700283
• 作为产物：
  描述：

  2-[2-(3,4-dihydro-(2H)-naphthalenylidene)ethyl]-2-methyl-1,3-cyclopentanedione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氯苯 为溶剂， 反应 1.5h， 以87%的产率得到
  参考文献：
  名称：

  Pentacyclic Compounds by Samarium Diiodide‐Induced Cascade Cyclizations of Naphthyl‐Substituted 1,3‐Diones

  摘要：

  AbstractTreatment of naphthyl‐substituted cyclopentane‐1,3‐diones with the samarium diiodide‐ hexamethylphosphoramide (HMPA) complex in the presence of tert‐butyl alcohol provided the expected tetracyclic diols with steroid‐like structures. Surprisingly, reactions without the proton source led to the efficient formation of a new pentacyclic diol. In this case the toxic additive HMPA could be substituted by a combination of lithium bromide (in situ generation of samarium dibromide) and N,N‐dimethylimidazolidone. The styrene‐like alkene moiety of this product was used to prepare an ensemble of highly substituted pentacyclic steroid‐like compounds.

  DOI：

  10.1002/adsc.200700283

文献信息

• Pentacyclic Compounds by Samarium Diiodide‐Induced Cascade Cyclizations of Naphthyl‐Substituted 1,3‐Diones
  作者：Ulrike K. Wefelscheid、Hans‐Ulrich Reissig

  DOI：10.1002/adsc.200700283

  日期：2008.1.4

  AbstractTreatment of naphthyl‐substituted cyclopentane‐1,3‐diones with the samarium diiodide‐ hexamethylphosphoramide (HMPA) complex in the presence of tert‐butyl alcohol provided the expected tetracyclic diols with steroid‐like structures. Surprisingly, reactions without the proton source led to the efficient formation of a new pentacyclic diol. In this case the toxic additive HMPA could be substituted by a combination of lithium bromide (in situ generation of samarium dibromide) and N,N‐dimethylimidazolidone. The styrene‐like alkene moiety of this product was used to prepare an ensemble of highly substituted pentacyclic steroid‐like compounds.