1,1-Dichloro-3,6-dimethoxy-1a,2,7,7a-tetrahydro-1H-cyclopropanaphthalene | 153202-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,1-Dichloro-3,6-dimethoxy-1a,2,7,7a-tetrahydro-1H-cyclopropanaphthalene
• 英文别名: 1,1-Dichloro-3,6-dimethoxy-1a,2,7,7a-tetrahydrocyclopropa[b]naphthalene
• CAS: 153202-78-9
• 化学式: C₁₃H₁₄Cl₂O₂
• 分子量: 273.159
• InChiKey: PYUKKESNEOMQAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1-Dichloro-3,6-dimethoxy-1a,2,7,7a-tetrahydro-1H-cyclopropanaphthalene 在 potassium tert-butylate 、 银 作用下， 生成 1,4-Dimethoxy-6-(tert-butoxymethyl)naphthalene
  参考文献：
  名称：

  1 H-cyclopropa(b)naphthalene-3,6-dione

  摘要：

  Cerium ammonium nitrate demethylation and oxidation of 3,6-dimethoxy-1H-cyclopropa[b]-naphthalene 6 provides 1H-cyclopropa[b]naphthalene-3,6-dione 8 as the first stable cyclopropaquinone.

  DOI：

  10.1039/p19930002239
• 作为产物：
  描述：

  cis-5,8,9,10-tetrahydronaphtho-1,4-quinone 在 potassium carbonate 作用下， 生成 1,1-Dichloro-3,6-dimethoxy-1a,2,7,7a-tetrahydro-1H-cyclopropanaphthalene
  参考文献：
  名称：

  1 H-cyclopropa(b)naphthalene-3,6-dione

  摘要：

  Cerium ammonium nitrate demethylation and oxidation of 3,6-dimethoxy-1H-cyclopropa[b]-naphthalene 6 provides 1H-cyclopropa[b]naphthalene-3,6-dione 8 as the first stable cyclopropaquinone.

  DOI：

  10.1039/p19930002239

文献信息

• Methylidenecycloproparenes: Novel Compounds with Fascinating Properties
  作者：Brian Halton、Peter Stang

  DOI：10.1055/s-1997-723

  日期：1997.2

  Proton abstraction from the methylene position of a cycloproparene provides the corresponding C1 anion that can be intercepted by a carbonyl-containing compound to provide a wide range of novel methylidenecycloproparenes. The physical and chemical aspects of this comparatively new class of surprisingly stable, strained compounds have been explored. The present account provides a perspective on these developments from the initial experiments in the Utah laboratories.

  从环丙烯环的甲叉位质子抽象化生成的相应C1阴离子，能够被含羰基的化合物捕获，从而获得广泛的、新型的亚甲基环丙烯类化合物。人们已经探讨了这类相对较新的、出乎意料的稳定性大、张力高的化合物的物理和化学性质。本文从犹他实验室最初的实验研究简述了这些进展。
• Studies in the cycloproparene series: oxygen-containing 1H-cyclopropa[b]naphthalenes and their methylidene derivatives
  作者：Brian Halton、Andrew J. Kay、Zha Zhi-Mei、Roland Boeseb、Thomas Haumann

  DOI：10.1039/p19960001445

  日期：——

  3,6-Dimethoxy-1H- cyclopropa[b]naphthalene 4 is available from 1,4-benzoquinone in four steps in 27–28% overall yield. The diether 4 provides a range of methylidene derivatives 15a–e by way of the disilyl compound 14, and is efficiently demethylated by cerium(IV) ammonium nitrate to provide 1H-cyclopropa[b]naphthalene-3,6-dione 16 (85%) whose crystal structure is reported. Quinone 16 is the first stable

  3，6 -二甲氧基- 1 H ^ -环丙[ b ]萘图4是得自1,4-苯醌在27-28％总产率四个步骤。二醚4提供了由二甲硅烷基化合物14的方式的范围亚甲基衍生物15A-E的，并且被有效地由铈（IV）铵脱甲基化，以提供1个ħ -cyclopropa [ b ]萘-3，6 -二酮16（85 ％）报告其晶体结构。醌16是第一个稳定的环丙基醌，但它不易转化为1-C外环烯烃。描述了化合物的化学性质，讨论了其光谱数据，并提供了16的循环伏安法。
• 1 H-cyclopropa(b)naphthalene-3,6-dione
  作者：Brian Halton、Andrew J. Kay、Zha Zhi-mei

  DOI：10.1039/p19930002239

  日期：——

  Cerium ammonium nitrate demethylation and oxidation of 3,6-dimethoxy-1H-cyclopropa[b]-naphthalene 6 provides 1H-cyclopropa[b]naphthalene-3,6-dione 8 as the first stable cyclopropaquinone.