5-bromodibenzosuberene | 59436-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 5-bromodibenzosuberene
• 英文别名: 2-Bromotricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaene
• CAS: 59436-15-6
• 化学式: C₁₅H₁₁Br
• 分子量: 271.156
• InChiKey: GCEQIDAWTMTTLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  366.6±31.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5-bromodibenzosuberene 在 对硝基甲苯 、 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以53%的产率得到5-二苯并环庚烯酮
  参考文献：
  名称：

  亚硝基芳烃催化 HFIP 辅助的芳甲基卤化物在有氧条件下转化为芳香羰基

  摘要：

  一种不含稀有金属的亲核亚硝基芳烃催化，伴随着高度氢键供体 (HBD) 溶剂，1,1,1,3,3,3-六氟-2-丙醇 (HFIP)，有机催化将芳甲基卤化物转化为芳香羰基化合物。该协议提供了一种有效的方法，可以在温和的反应条件下获得具有良好化学选择性的多种芳香羰基化合物。HFIP 活化芳甲基卤化物以产生稳定的碳正离子以及在大气 O 2存在下原位生成的羟胺自动氧化为亚硝基芳烃是成功的关键。

  DOI：

  10.1021/acs.orglett.1c02272
• 作为产物：
  描述：

  5H-二苯并[Α,D]环庚三烯-5-醇 在 三溴化磷 作用下， 以 苯 为溶剂， 生成 5-bromodibenzosuberene
  参考文献：
  名称：

  与同源的五元环自由基环化相比，优先选择六元环自由基环化的明确例子。5- [溴烷基] -5H-二苯并[ a，d ]环庚烯与Bu 3 SnH的反应

  摘要：

  5- [2-溴-乙基] -5H-二苯并[ a，d ]环庚烯4与Bu 3 SnH和AIBN的自由基环化反应导致环化烃5为主要产物，而溴代衍生物8与Bu 3 SnH和AIBN仅给出了直链产物9。提出了基于AM1法计算的二苯并[ a，d ]环庚烯体系的构象刚度的解释。

  DOI：

  10.1016/0040-4039(96)00695-8

文献信息

• Benzylphosphonic acid inhibitors of human prostatic acid phosphatase
  作者：Charles F. Schwender、Scott A. Beers、Elizabeth A. Malloy、Jacqueline J. Cinicola、David J. Wustrow、Keith D. Demarest、Jerold Jordan

  DOI：10.1016/0960-894x(96)00018-2

  日期：1996.2

  A series of alpha-substituted benzylphosphonic acids is described as inhibitors of human prostatic acid phosphatase, an enzyme which has been used as a model to study aryl phosphatases. The most potent inhibitors in this series are 2-trifluoromethylbenzhydrylphosphonic acid (9 mu M), and alpha-(2-phenylethyl)benzylphosphonic acid (14 mu M) The structure-activity studies suggest that bulk tolerance beyond the phosphate binding area limits the steric or hydrophobic contribution to inhibitor potency achieved through alpha-carbon substitution.
• REACTIVITY OF METHYLENETRIPHENYLPHOSPHORANES HAVING TWO PHENYL GROUPS CONSTRAINED WITH ETHANO OR ETHENO BRIDGE
  作者：Yasuhiko Kawamura、Yasunori Iwano、Noboru Watanabe、Tokunaru Horie、Masao Tsukayama

  DOI：10.1080/10426509808036985

  日期：1998.1.1

  Methylenetriphenylphosphoranes having two phenyl groups tied together with ethano or etheno bridge were prepared by conventional ways in order to suppress delocalization of an ylide-carbanion by deforming geometrical arrangement of phenyl groups from that of the diarylmethylene derivative and hence to elevate reactivities of diarylmethylenephosphoranes. These P-ylides were, however, still unreactive with usual aldehydes and ketones. The reasons, are deliberated by molecular orbital calculations and the P-31-NMR data. The HOMO orbitals of ethano-bridged and etheno-bridged diarylmethylenephosphoranes are located on a monoarylcarbanion and a carbanion, respectively. Although these tendencies are auspicious to enhance the Wittig reactivity of them, the electron densities of the ylidic carbons are still insufficient. P-31-NMR chemical shifts of the ylides revealed that the objective P-ylides do not have a large extent of the ylide-contribution in the ylide-yllene resonance. Meanwhile, they reacted readily with tetrahalo o-quinones to give 1,3-dioxoles in good yields. Thermochromic behavior of one of the precursors, dibenzosuberenylphosphonium salt, was observed at 80 degreesC in acetonitrile in the presence of trace perchloric acid. The colored species is elucidated as dibenzo[a,e]tropylium cation.