3-bromo-4-methoxyindan-1-one | 256432-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 3-bromo-4-methoxyindan-1-one
• 英文别名: 3-Bromo-4-methoxy-2,3-dihydroinden-1-one
• CAS: 256432-69-6
• 化学式: C₁₀H₉BrO₂
• 分子量: 241.084
• InChiKey: GEEAOEZPABMPII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-4-methoxyindan-1-one 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 4-Methoxy-2-[1-(4-methoxy-phenyl)-meth-(Z)-ylidene]-3-piperidin-1-yl-indan-1-one
  参考文献：
  名称：

  Gupta; Nautiyal; Jhingran, Indian journal of chemistry, 1981, vol. 20 B, # 4, p. 303 - 307

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基-1-茚酮 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 2.5h， 生成 3-bromo-4-methoxyindan-1-one
  参考文献：
  名称：

  含五元环的对映纯角稠合[2.2]对环环烷的合成

  摘要：

  基于（S）-（+）-4-乙烯基[2.2]对环芳烃的狄尔斯-阿尔德环加成反应，通过两步法合成了含五元环的旋光角聚[2.2]对环芳烃。提出了通过NMR光谱进行的结构分析。这些含有环戊烷环的Heliconophanes表现出非常高的比旋度。已经就通过用环戊烷环取代苯单元引起的结构改变来讨论了这种现象。

  DOI：

  10.1016/s0957-4166(02)00833-9

文献信息

• An Efficient Synthetic Approach to Substituted Penta- and Hexahelicenes
  作者：Lucio Minuti、Aldo Taticchi、Assunta Marrocchi、Eszter Gacs-Baitz、Roberta Galeazzi

  DOI：10.1002/(sici)1099-0690(199911)1999:11<3155::aid-ejoc3155>3.0.co;2-s

  日期：1999.11

  A two-step synthetic approach to penta- and hexahelicenes substituted at the terminal aromatic rings has been studied. This approach is based on the Diels–Alder reaction of 5,5′,8,8′-tetramethyl-3,3′,4,4′-tetrahydro-[1,1′]-binaphthalene (2b), 3-vinyl-1,2-dihydronaphthalene (5a), 5,8-dimethyl-3-vinyl-1,2-dihydronaphthalene (5b) and 3-vinyl-1,2-dihydrophenanthrene (15) followed by the aromatization of

  已经研究了在末端芳环处取代的五和六螺旋的两步合成方法。该方法基于 5,5',8,8'-四甲基-3,3',4,4'-四氢-[1,1']-联萘 (2b), 3-乙烯基的 Diels-Alder 反应-1,2-二氢萘 (5a)、5,8-二甲基-3-乙烯基-1,2-二氢萘 (5b) 和 3-乙烯基-1,2-二氢菲 (15)，然后对环加合物进行芳构化。该方法灵活、高效，可广泛应用于多种苯类和非苯类五和六螺旋烯的合成。使用半经验量子方法AM1计算了螺旋3、9、10、13、14、17和18的外消旋能垒。计算值表明，当在末端芳环的内部位置引入甲基时，外消旋化势垒显着增加。
• High pressure Diels–Alder reactions of (+)-nopadiene with cycloalkenones
  作者：Lucio Minuti、Aldo Taticchi、Assunta Marrocchi、Alessandra Broggi、Eszter Gacs-Baitz

  DOI：10.1016/j.tetasy.2004.02.019

  日期：2004.4

  derivatives, prepared in situ from the corresponding bromoindanones, have been studied. All cycloadditions are regioselective and endo-anti diastereoselective. The best yields were obtained when the Diels–Alder reactions were carried out under high pressure conditions. All new compounds were characterized by their spectroscopic data, in particular by extensive NMR investigations.

  已经研究了由相应的溴茚满酮原位制备的（+）-pad丁烯与2-环戊烯-1-酮，2-环己烯-1-酮，4-氧代-2-环戊烯基乙酸酯和两种茚满酮衍生物之间的环加成。所有的环加成是区域选择性的和内-非非对映选择性的。当在高压条件下进行狄尔斯-阿尔德反应时，可获得最佳产率。所有新化合物的光谱数据，尤其是广泛的NMR研究，都对其特征进行了表征。
• The Preparation of Helical Cyclophanes Containing Five-membered Rings
  作者：Assunta Marrocchi、Lucio Minuti、Aldo Taticchi、Ina Dix、Henning Hopf、Eszter Gacs-Baitz、Peter G. Jones

  DOI：10.1002/1099-0690(200111)2001:22<4259::aid-ejoc4259>3.0.co;2-i

  日期：2001.11

  Cycloadditions between the indenone derivatives prepared in situ from the bromides 12a and 12b and 4-vinyl[2.2]paracyclophane (11) yielded the Diels-Alder adducts 13a and 13b in acceptable yields. When these were heated in the presence of DDQ in toluene, the fluorenophanes 14a and 14b were produced in good yields. The diol 17 obtained from the tetralonophane 15 on treatment with POCl3/pyridine was dehydrated to the diene 18, which could be trapped by p-benzoquinone (19) to provide the cycloadducts 20 and 21; the former was oxidized to the latter by DDQ treatment. Although the even more highly annelated helical phane system 22 could be prepared from 17 and 12a, its aromatization to the ketone 24 or the hydrocarbon 25 failed. All new compounds were characterized by their spectroscopic data, in particular by extensive NMR investigations. A single-crystal X-ray structure analysis for the parent hydrocarbon phenanthreno[2.2]paracyclophane (5) is reported.
• GUPTA, R. C.;NAUTIYAL, PRAVEENA;JHINGRAN, AKHIL, G.;KAMBOJ, V. P.;SETTY, +, INDIAN J. CHEM., 1981, 20, N 4, 303-307
  作者：GUPTA, R. C.、NAUTIYAL, PRAVEENA、JHINGRAN, AKHIL, G.、KAMBOJ, V. P.、SETTY, +

  DOI：——

  日期：——