2-[2-(3,4-dihydro-(2H)-naphthalenylidene)ethyl]-2-methyl-1,3-cyclopentanedione | 25188-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-[2-(3,4-dihydro-(2H)-naphthalenylidene)ethyl]-2-methyl-1,3-cyclopentanedione
• 英文别名: 2-[2-(3,4-dihydro-2H-naphthalen-1-ylidene)ethyl]-2-methylcyclopentane-1,3-dione
• CAS: 25188-14-1
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: IBZOIJWGOJGCCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-vinyl-1-tetralol 以 水 、 甲苯 为溶剂， 反应 10.0h， 生成 2-[2-(3,4-dihydro-(2H)-naphthalenylidene)ethyl]-2-methyl-1,3-cyclopentanedione
  参考文献：
  名称：

  催化不对称Torgov环化：（+）-Estrone的简明全合成

  摘要：

  描述了一种新型的高度布朗斯台德酸性二硝基取代的二磺酰亚胺催化的不对称Torgov环化反应。该反应以优异的产率和对映选择性提供了Torgov二烯和各种类似物。该方法用于（+）-雌酮的非常短的合成中。

  DOI：

  10.1002/anie.201404909

文献信息

• Catalytic Asymmetric Torgov Cyclization: A Concise Total Synthesis of (+)-Estrone
  作者：Sébastien Prévost、Nathalie Dupré、Markus Leutzsch、Qinggang Wang、Vijay Wakchaure、Benjamin List

  DOI：10.1002/anie.201404909

  日期：2014.8.11

  dinitro‐substituted disulfonimide, is described. The reaction delivers the Torgov diene and various analogues with excellent yields and enantioselectivity. This method was applied in a very short synthesis of (+)‐estrone.

  描述了一种新型的高度布朗斯台德酸性二硝基取代的二磺酰亚胺催化的不对称Torgov环化反应。该反应以优异的产率和对映选择性提供了Torgov二烯和各种类似物。该方法用于（+）-雌酮的非常短的合成中。
• 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.