4-nitro-1H-cyclobutanaphthalene | 97383-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-nitro-1H-cyclobutanaphthalene
• 英文别名: 6-Nitrotricyclo[5.3.1.03,11]undeca-1(11),3,5,7,9-pentaene
• CAS: 97383-48-7
• 化学式: C₁₁H₇NO₂
• 分子量: 185.182
• InChiKey: YRNXWKJZQFTCJE-UHFFFAOYSA-N

物化性质

• 熔点：
  124-125 °C
• 沸点：
  353.1±21.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-nitro-1H-cyclobutanaphthalene 在 aluminium amalgam 、 水 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 2.0h， 生成 1-(1H-cyclobutanaphthalen-4-yl)-3-phenylthiourea
  参考文献：
  名称：

  Aromatic substitution and addition reactions of 1H-cyclobuta[de]naphthalenes

  摘要：

  DOI：

  10.1021/jo00350a053
• 作为产物：
  描述：

  1H-cyclobutanaphthalene 在 硝酸 、 乙酸酐 作用下， 反应 1.0h， 以85%的产率得到4-nitro-1H-cyclobutanaphthalene
  参考文献：
  名称：

  Aromatic substitution and addition reactions of 1H-cyclobuta[de]naphthalenes

  摘要：

  DOI：

  10.1021/jo00350a053

文献信息

• Aromatic substitution and addition reactions of 1-cyclobuta[]naphthalenes
  作者：F.E. Friedli、H. Shechter

  DOI：10.1016/s0040-4039(00)98421-1

  日期：1985.1

  1-Cyclobuta[]naphthalenes undergo electrophilic substitutions at their C-4 and their C-5 positions; photolytic bromination of 1-cyclobuta[]naphthalene yields 1,2,3,4 tetrabromo-1,2,3,4-tetrahydro-1-cyclobuta[]naphthalene.

  1- Cyclobuta [ ]萘在其C-4和C-5位置进行亲电取代；1-环丁[ ]萘的光解溴化反应生成1,2,3,4四溴-1,2,3,4-四氢-1-环丁[ ]萘。
• Synthesis of <i>peri</i>-Cyclobutarenes by Thermolysis of [Methoxy(trimethylsilyl)methyl]arenes
  作者：Thomas A. Engler、Harold Shechter

  DOI：10.1021/jo981104j

  日期：1999.6.1

  [Methoxy(trimethylsilyl)methyl]arenes are readily prepared by reactions of chlorotrimethylsilane with (alpha-methoxy)arenylmethyllithium reagents as obtained from (methoxymethyl)arenes and t-BuLi. The [methoxy(trimethylsilyl)methyl] arenes eliminate methoxytrimethylsilane at 525-675 degrees C/0.05-0.10 mm to yield peri-cyclobutarenes as derived from arenylcarbenes. Of importance is the fact that the initial arenylcarbenes generated insert into adjacent peri C-H bonds and/or isomerize to other arenylcarbenes that insert into their peri C-H bonds to give peri-cyclobutarenes. Thus, flash-vacuum pyrolysis of 1-[methoxy(trimethylsilyl)methyl]naphthalene (13) at 575-675 degrees C/0.05-0.10 mm yields 1H-cyclobuta[de]naphthalene (6, up to 39%) in practical quantities. 2-[Methoxy(trimethylsilyl)methyl]naphthalene (23) also affords 6 as a major thermolysis product. At 510 degrees C/ 0.05-0.10 mm 4-methoxy-1-[methoxy(trimethylsilyl)methyl]naphthalene (29) decomposes to 4-methoxy-1H-cyclobuta[de]naphthalene (31, 46%). Under similar conditions, 2-methoxy-1-[methoxy(trimethylsilyl)methyl]naphthalene (33) converts to 1,2-dihyrdronaphtho[2,1-b]furan (35, 64%) and naphtho[2,1-b]furan (36, 31%), presumably by insertion of 2-methoxy-1-naphthylcarbene (34) into a C-H bond of its o-methoxy group and then dehydrogenation of the resultant dihydrofuran. Further, 1-[methoxy(trimethylsilyl)methyl]-6-methylnaphthalene (39) pyrolyzes (510 degrees C/0.10-0.20 mm) to 6-methyl-1-naphthylcarbene (40), which isomerizes in part to 7-methyl-1-naphthylcarbene (49); carbenes 40 and 49 then undergo peri C-H insertion to give 3-methyl-1H-cyclobuta[de]naphthalene (41) and 2-methyl-1H-cyclobuta[de]naphthalene (42) in an 8:1 ratio and a combined yield of 44%. The pyrolytic method is particularly valuable for preparing higher peri single carbon atom bridged arenes such as 4H-cyclobuta[jk]phenanthrene (53, 65%) and 3H-cyclobuta[cd]pyrene (59, 86%).
• FRIEDLI, F. E.;SHECHTER, H., J. ORG. CHEM., 1985, 50, N 26, 5710-5716
  作者：FRIEDLI, F. E.、SHECHTER, H.

  DOI：——

  日期：——
• FRIEDLI, F. E.;SHECHTER, H., TETRAHEDRON LETT., 1985, 26, N 9, 1157-1158
  作者：FRIEDLI, F. E.、SHECHTER, H.

  DOI：——

  日期：——