1-(methoxymethyl)anthracene | 70909-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(methoxymethyl)anthracene
• 英文别名: 1-Methoxymethyl-anthracen
• CAS: 70909-33-0
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: AOKCIQXTBVPQHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(methoxymethyl)anthracene 在 四甲基乙二胺 、 叔丁基锂 作用下， 反应 0.25h， 生成 2H-cyclopentafluorene
  参考文献：
  名称：

  Preparative Methodology and Pyrolytic Behavior of Anthrylmonocarbenes:  Synthesis and Chemistry of 1H-Cyclobuta[de]anthracene

  摘要：

  This study involves (1) the behavior of organolithium reagents (1-6), (2) development of efficient methods for preparing 9(7)- and 1(8)-[methoxy(trimethylsilyl)methyl] anthracenes and their analogues, (3) the intramolecular chemistry of the 9(9)- and 1(l0)-anthrylcarbenes generated by pyrolyses of 7 and 8, respectively, and (4) investigation of thermal behavior and bromination of the 1H-cyclobuta[de]anthracene (11) obtained from 9 or 10. alpha-Methoxy-9-anthrylmethyllithium (1), prepared from 9-(methoxymethyl)anthracene (14) and t-BuLi in TMEDA/Et2O/pentane, reacts at C-10 with D2O, chlorotrimethylsilane, dimethyl sulfate, benzoyl chloride, acetaldehyde, benzaldehyde, and acetone to give, after neutralization, 9,10-dihydro-9-(methoxymethylene)-10-substituted- anthracenes 15 and 21a-f. However, lithiation of 9-(thiomethoxymethyl)anthracene (25) with t-BuLi/TMEDA/Et2O/pentane occurs by an apparent radical-anion displacement process to give 9-anthrylmethyllithium (3), which then reacts with chlorotrimethylsilane to yield 9-(trimethylsilylmethyl)anthracene (28). Similarly, 28 is formed from 25 and from 9-(trimethylsilyloxymethyl)-anthracene (29) with lithium and then chlorotrimethylsilane. The electrophiles D2O, dimethyl sulfate, and benzaldehyde react with 3 at its methyl and its C-10 positions. [Methoxy(trimethylsilyl)methyl]arenes 40-42 and 7 are obtained by reactions of their aryllithium and arylmagnesium bromide precursors with bromo(methoxy)methyltrimethylsilane (39). 1-(Methoxymethyl)anthracene (45) is converted conveniently by t-BuLi and chlorotrimethylsilane to 8. Flash-vacuum pyrolyses of 7 and 8 yield 11 preparatively; 11 then thermolyzes to 2H-cyclopenta[jk]fluorene (46). Decomposition of 9-deuterio-10-[methoxy(trimethylsilyl)methyl]anthracene (55) at 650 degrees C/10(-3) mm results in 10(56)- and 1(57)-deuteriocyclobutanthracenes, thus revealing that the 10-deuterio-9-anthrylcarbene inserts to give 56 and also isomerizes extensively before yielding 57. Of note is that 56 isomerizes thermally by C-10-D movement to form 2-deuteriocyclopentafluorene 58, 57 rearranges by Clo-H movement to yield deuteriocyclopentafluorene 59, and 58 and 59 equilibrate 1,5-sigmatropically. Possible mechanisms for the isomerizations of 56 and 57 are outlined. Further, bromine adds rapidly to 11 to form 9,10-dibromo-9,10-dihydro-1H-cyclobuta[de]anthracene (94), which eliminates HBr on warming to yield 10-bromo-1H-cyclobuta[de]anthracene (95).

  DOI：

  10.1021/jo981105b

文献信息

• Photomask and manufacturing method of an electronic device therewith
  申请人：——

  公开号：US20020086222A1

  公开（公告）日：2002-07-04

  In the step of manufacturing a photomask, an opaque pattern is formed by using a photosensitive resin composition containing a specified light absorbent, which then used to manufacture a photomask for KrF excimer laser lithography in a short manufacturing time and at a reduced cost. Accordingly, the manufacturing time and the cost for semiconductor integrated circuit devices is reduced.

  在制造光掩膜的步骤中，通过使用含有特定光吸收剂的光敏树脂组合物形成不透明图案，然后用它来制造用于 KrF 准分子激光光刻的光掩膜，制造时间短，成本低。因此，半导体集成电路设备的制造时间和成本都得以降低。
• Photo mask
  申请人：——

  公开号：US20030129505A1

  公开（公告）日：2003-07-10

  Providing a photo mask for KrF excimer laser lithography, which can be produced with high accuracy and low defects in a smaller number of steps. A photo mask for KrF excimer laser lithography according to the present invention is one in which a resist pattern 18 efficiently absorbing a KrF excimer laser light (wavelength: about 248 nm) is formed directly on a quartz substrate 10. The resist pattern 18 comprises: an aqueous alkali-soluble resin having a high light shielding property, which incorporates a naphthol structure having at least one hydroxyl group bound to a naphthalene nucleus; or a radiation sensitive resist having, as a main component, an aqueous alkali-soluble resin containing a derivative of the above-mentioned aqueous alkali-soluble resin as a resin matrix.

  提供一种用于 KrF 准分子激光光刻的光掩膜，它可以用较少的步骤生产出高精度和低缺陷的光掩膜。根据本发明，用于 KrF 准分子激光光刻的光掩膜是一种抗蚀剂图案 18 在石英基底上直接形成能有效吸收 KrF 准分子激光（波长：约 248 纳米）的光刻胶图案 18。 10. 抗蚀图案 18 包括：具有高光屏蔽性能的水性碱溶性树脂，其中包含一个萘酚结构，该萘酚结构具有至少一个与萘核结合的羟基；或辐射敏感抗蚀剂，其主要成分为水性碱溶性树脂，其中含有上述水性碱溶性树脂的衍生物作为树脂基体。
• US6790564B2
  申请人：——

  公开号：US6790564B2

  公开（公告）日：2004-09-14
• US7005216B2
  申请人：——

  公开号：US7005216B2

  公开（公告）日：2006-02-28
• Preparative Methodology and Pyrolytic Behavior of Anthrylmonocarbenes:  Synthesis and Chemistry of 1<i>H</i>-Cyclobuta[<i>de</i>]anthracene
  作者：J. Kirby Kendall、Thomas A. Engler、Harold Shechter

  DOI：10.1021/jo981105b

  日期：1999.6.1

  This study involves (1) the behavior of organolithium reagents (1-6), (2) development of efficient methods for preparing 9(7)- and 1(8)-[methoxy(trimethylsilyl)methyl] anthracenes and their analogues, (3) the intramolecular chemistry of the 9(9)- and 1(l0)-anthrylcarbenes generated by pyrolyses of 7 and 8, respectively, and (4) investigation of thermal behavior and bromination of the 1H-cyclobuta[de]anthracene (11) obtained from 9 or 10. alpha-Methoxy-9-anthrylmethyllithium (1), prepared from 9-(methoxymethyl)anthracene (14) and t-BuLi in TMEDA/Et2O/pentane, reacts at C-10 with D2O, chlorotrimethylsilane, dimethyl sulfate, benzoyl chloride, acetaldehyde, benzaldehyde, and acetone to give, after neutralization, 9,10-dihydro-9-(methoxymethylene)-10-substituted- anthracenes 15 and 21a-f. However, lithiation of 9-(thiomethoxymethyl)anthracene (25) with t-BuLi/TMEDA/Et2O/pentane occurs by an apparent radical-anion displacement process to give 9-anthrylmethyllithium (3), which then reacts with chlorotrimethylsilane to yield 9-(trimethylsilylmethyl)anthracene (28). Similarly, 28 is formed from 25 and from 9-(trimethylsilyloxymethyl)-anthracene (29) with lithium and then chlorotrimethylsilane. The electrophiles D2O, dimethyl sulfate, and benzaldehyde react with 3 at its methyl and its C-10 positions. [Methoxy(trimethylsilyl)methyl]arenes 40-42 and 7 are obtained by reactions of their aryllithium and arylmagnesium bromide precursors with bromo(methoxy)methyltrimethylsilane (39). 1-(Methoxymethyl)anthracene (45) is converted conveniently by t-BuLi and chlorotrimethylsilane to 8. Flash-vacuum pyrolyses of 7 and 8 yield 11 preparatively; 11 then thermolyzes to 2H-cyclopenta[jk]fluorene (46). Decomposition of 9-deuterio-10-[methoxy(trimethylsilyl)methyl]anthracene (55) at 650 degrees C/10(-3) mm results in 10(56)- and 1(57)-deuteriocyclobutanthracenes, thus revealing that the 10-deuterio-9-anthrylcarbene inserts to give 56 and also isomerizes extensively before yielding 57. Of note is that 56 isomerizes thermally by C-10-D movement to form 2-deuteriocyclopentafluorene 58, 57 rearranges by Clo-H movement to yield deuteriocyclopentafluorene 59, and 58 and 59 equilibrate 1,5-sigmatropically. Possible mechanisms for the isomerizations of 56 and 57 are outlined. Further, bromine adds rapidly to 11 to form 9,10-dibromo-9,10-dihydro-1H-cyclobuta[de]anthracene (94), which eliminates HBr on warming to yield 10-bromo-1H-cyclobuta[de]anthracene (95).