1-indanone O-(tert-butyldimethylsilyl)oxime | 251980-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1-indanone O-(tert-butyldimethylsilyl)oxime
• 英文别名: (E)-N-[tert-butyl(dimethyl)silyl]oxy-2,3-dihydroinden-1-imine
• CAS: 251980-46-8
• 化学式: C₁₅H₂₃NOSi
• 分子量: 261.439
• InChiKey: BGLXICITMWJZNQ-JQIJEIRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-indanone O-(tert-butyldimethylsilyl)oxime 在 硼烷四氢呋喃络合物 作用下， 以88%的产率得到1,2,3,4-四氢喹啉
  参考文献：
  名称：

  硼烷还原O-硅烷化芳族酮肟的立体和电子效应

  摘要：

  用硼烷-THF还原在TMS，TBS，TIPS和MDPS基团上被TMS，TBS，TIPS和MDPS基团取代的4-甲氧基苯乙酮肟，获得了4-甲氧基-N-乙基苯胺作为主要产物，在这种情况下产率高达95％更阻碍了TIPS集团的发展。2-甲氧基-和2,4-甲氧基苯乙酮O -TBS肟仅产生重排的仲苯胺。还原1-茚满酮O - TBS肟仅提供四氢喹啉，而2-茚满酮类似物仅提供2-氨基茚满。

  DOI：

  10.1016/s0040-4039(00)01109-6
• 作为产物：
  描述：

  1-茚酮肟 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以69%的产率得到1-indanone O-(tert-butyldimethylsilyl)oxime
  参考文献：
  名称：

  Efficient α-alkylation and silylation of aromatic O-tert-butyldimethylsilyl ketoximes

  摘要：

  The a-alkylation and silylation of para substituted acetophenones, 1- and 2-indanone (O-TBS) oximes at various reaction conditions, were studied. Optimum conversions from 82% to 100% were afforded for the alkylation and silylation of these (O-TBS) ketoximes with LDA at -78 degrees C, using electrophiles, such as, methyl iodide, ethylbromide, benzyl bromide and trimethylchlorosilane. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00731-0

文献信息

• Steric and electronic effects on the reduction of O-silylated aromatic ketoximes with borane
  作者：Margarita Ortiz-Marciales、Dyliana Figueroa、José A López、Melvin De Jesús、Rafael Vega

  DOI：10.1016/s0040-4039(00)01109-6

  日期：2000.8

  aniline as the principal product, up to a 95% yield in the case of the more hindered TIPS group. The 2-methoxy- and 2,4-methoxyacetophenone O-TBS oximes produced only the rearranged secondary aniline. Reduction of 1-indanone O-TBS oximes afforded only the tetrahydroquinoline, whereas the 2-indanone analog provided only 2-aminoindan.

  用硼烷-THF还原在TMS，TBS，TIPS和MDPS基团上被TMS，TBS，TIPS和MDPS基团取代的4-甲氧基苯乙酮肟，获得了4-甲氧基-N-乙基苯胺作为主要产物，在这种情况下产率高达95％更阻碍了TIPS集团的发展。2-甲氧基-和2,4-甲氧基苯乙酮O -TBS肟仅产生重排的仲苯胺。还原1-茚满酮O - TBS肟仅提供四氢喹啉，而2-茚满酮类似物仅提供2-氨基茚满。
• Facile Rearrangement of <i>O</i>-Silylated Oximes on Reduction with Boron Trifluoride/Borane
  作者：Margarita Ortiz-Marciales、Luis D. Rivera、Melvin De Jesús、Sandraliz Espinosa、Josúe A. Benjamin、Orlando E. Casanova、Irving G. Figueroa、Sheila Rodríguez、Wilbert Correa

  DOI：10.1021/jo0516178

  日期：2005.11.1

  Aromatic O-triisopropylsilyl ketoximes were efficiently rearranged to cyclic and acyclic aniline derivatives on reduction with BF3-ethearate /borane. The bulk of the substituents on the silicon atom, the size of the aliphatic ring, and the presence of alkoxy substituents on the aryl group all play an important role in the aniline.

  在用BF 3-硬脂酸酯/硼烷还原时，将芳族O-三异丙基甲硅烷基酮肟有效地重排为环状和无环苯胺衍生物。硅原子上的大部分取代基，脂族环的大小以及芳基上烷氧基取代基的存在均在苯胺中起重要作用。
• Efficient α-alkylation and silylation of aromatic O-tert-butyldimethylsilyl ketoximes
  作者：Margarita Ortiz-Marciales、Melvin De Jesús、Lemuel Quiñones、Dyliana Figueroa、Yadira L. Montes、Carlos Burgos、Benjamin Moctezuma

  DOI：10.1016/s0040-4020(99)00731-0

  日期：1999.10

  The a-alkylation and silylation of para substituted acetophenones, 1- and 2-indanone (O-TBS) oximes at various reaction conditions, were studied. Optimum conversions from 82% to 100% were afforded for the alkylation and silylation of these (O-TBS) ketoximes with LDA at -78 degrees C, using electrophiles, such as, methyl iodide, ethylbromide, benzyl bromide and trimethylchlorosilane. (C) 1999 Elsevier Science Ltd. All rights reserved.