2,4,6-tri-tert-butylbenzonitrile oxide | 193344-24-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4,6-tri-tert-butylbenzonitrile oxide
• 英文别名: 2,4,6-tri-t-butylbenzonitrile oxide；2,4,6-tri(tert-butyl)phenylCNO；Benzonitrile, 2,4,6-tris(1,1-dimethylethyl)-, N-oxide；2,4,6-tritert-butylbenzonitrile oxide
• CAS: 193344-24-0
• 化学式: C₁₉H₂₉NO
• 分子量: 287.445
• InChiKey: MMDCYKMLNFOPMK-UHFFFAOYSA-N

物化性质

• 密度：
  0.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4,6-tri-tert-butylbenzonitrile oxide 、 2,4-bis(2,4,6-tri-t-butylphenyl)-1,3,2,4-dioxadiboretane 在 水 作用下， 生成 [Hydroxy-[2,4,6-tris[bis(trimethylsilyl)methyl]phenyl]boranyl]oxy-[2,4,6-tris[bis(trimethylsilyl)methyl]phenyl]borinic acid
  参考文献：
  名称：

  A novel approach to an oxoborane and its Lewis base complex

  摘要：

  Reaction of dimethyl sulfoxide (DMSO) with 1,3,2,4-dithiastannaboretane 3 bearing an extremely bulky aryl group, 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl (Tbt), an the baron atom gave an oxoborane (Tbt-B=O; 4), which formed a complex with DMSO stable in solution. The formation of the complex was confirmed by B-11 NMR and a [3+2] cycloaddition reaction with 2,4,6-tri-t-butylbenzonitrile oxide. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00929-5
• 作为产物：
  描述：

  2,4,6-tri-t-butylbenzaldehyde oxime 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以88%的产率得到2,4,6-tri-tert-butylbenzonitrile oxide
  参考文献：
  名称：

  Reactions of 1,3,5,2,4,6-trichalcogenatristannins and their derivatives with a nitrile oxide: synthesis, structure, and thermal behavior of oxachalcogenazastannoles

  摘要：

  2,2,4,4.6,6-Hexamethyl-1.3,5-trithia- and 1,3,5-triselena-2,4,6-tristannins reacted with 2,4,6-tri-t-butylbenzonitrile oxide to give 2,2-dimethyl-1,3-oxathia- and 1,3,5,2-oxaselenazastannoles. The reaction of 2,2,4,4-tetra-t-butyl-1,3,2,4-dithiadistannetane with 2,4,6-tri-t-butylbenzonitrile oxide gave 2,2-di-t-butyl-1,3,5,2-oxathiazastannole. The unusual thermal behavior of the oxachalcogenazastannole is also described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01443-5

文献信息

• Generation of 9-Stannaphenanthrene and Its Reactivities
  作者：Yoshiyuki Mizuhata、Nobuhiro Takeda、Takahiro Sasamori、Norihiro Tokitoh

  DOI：10.1246/cl.2005.1088

  日期：2005.8

  A neutral stannaaromatic compound, 9-stannaphenanthrene 1a bearing an efficient steric protection group, 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl (Tbt), was successfully generated by the reaction of the corresponding chlorostannane 2 with lithium 2,2,6,6-tetramethylpiperidide in THF at −78 °C. The generaion of 1a was indicated by the trapping experiments using MeOD, Mes*CNO, and 2,3-dimethyl-1,3-butadiene at the same temperature. However, 1a was found to undergo ready dimerization at room temperature to give the cis-[2 + 2] dimer 3 stereoselectively.

  在-78 °C的四氢呋喃中，相应的氯甾烷 2 与 2,2,6,6-四甲基哌啶锂反应，成功生成了一种中性链烷族化合物 9-链菲 1a，该化合物带有一个高效的立体保护基团 2,4,6-三[双（三甲基硅基）甲基]苯基 (Tbt)。在相同温度下使用 MeOD、Mes*CNO 和 2,3-二甲基-1,3-丁二烯进行的捕集实验表明生成了 1a。然而，研究发现 1a 在室温下可立即发生二聚反应，从而立体选择性地生成顺式[2 + 2]二聚体 3。
• Cyclic Chalcogenides Containing Group 13–15 Elements
  作者：Renji Okazaki

  DOI：10.1080/10426500108546529

  日期：2001.1.1

  polychalcogenides containing a variety of heavier main group elements of groups 13, 14, and 15 as ring members have been synthesized as stable crystalline compounds by taking advantage of an effective steric protection group, 2,4,6-tris[bis(trimethylsilyl)methyl]-phenyl (denoted as Tbt in this article). The molecular structures of tetrachalcogenametallolanes of group 14 elements, Tbt(R)ME4 (M = Si

  通过利用有效的空间保护基团 2,4,6-三[双(三甲基甲硅烷基)甲基]-苯基（在本文中表示为 Tbt）。X 分析了 14 族元素的四硫属元素金属烷、Tbt(R)ME4（M = Si、Ge、Sn 和 Pb；E = S、Se）和一些含有锑或硼原子作为环成员的多硫化物的分子结构射线晶体学来阐明这些新型环系统的骨架特征。
• 1,3,2,4-Diselenastannaboretane, a novel selenium-containing four-membered boracycle: synthesis, structure and thermal cycloreversion into a selenoxoborane
  作者：Mitsuhiro Ito、Norihiro Tokitoh、Renji Okazaki

  DOI：10.1039/a806478d

  日期：——

  Treatment of an overcrowded aryl trihydroborate bearing 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl (Tbt) group with Cp2TiSe5 followed by the addition of Ar2SnCl2 (Ar = Ph or Mes) and Ph3P resulted in the isolation of novel selenium-containing four-membered boracycles, 1,3,2,4-diselenastannaboretanes, the thermolysis of which in the presence of 2,3-dimethyl-1,3-butadiene or 2,4,6-tri-tert-butylbenzonitrile oxide indicated the formation of a novel class of boron-containing doubly bonded compound, an arylselenoxoborane (Tbt)BSe.

  用 Cp2TiSe5 处理带有 2,4,6-三[双(三甲基硅基)甲基]苯基 (Tbt) 基团的拥挤芳基三氢硼酸盐，然后添加 Ar2SnCl2（Ar = Ph 或 Mes）和 Ph3P，从而分离出新型硒-含有四元硼环化合物，1,3,2,4-二硒斯坦那硼烷，其在2,3-二甲基-1,3-丁二烯或2,4,6-三叔丁基苯甲腈氧化物存在下的热解表明形成一类新型含硼双键化合物，即芳基硒代硼烷 (Tbt)BSe。
• A novel approach to an oxoborane and its Lewis base complex
  作者：Mitsuhiro Ito、Norihiro Tokitoh、Renji Okazaki

  DOI：10.1016/s0040-4039(97)00929-5

  日期：1997.6

  Reaction of dimethyl sulfoxide (DMSO) with 1,3,2,4-dithiastannaboretane 3 bearing an extremely bulky aryl group, 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl (Tbt), an the baron atom gave an oxoborane (Tbt-B=O; 4), which formed a complex with DMSO stable in solution. The formation of the complex was confirmed by B-11 NMR and a [3+2] cycloaddition reaction with 2,4,6-tri-t-butylbenzonitrile oxide. (C) 1997 Elsevier Science Ltd.
• Reactions of 1,3,5,2,4,6-trichalcogenatristannins and their derivatives with a nitrile oxide: synthesis, structure, and thermal behavior of oxachalcogenazastannoles
  作者：Masaichi Saito、Susumu Nakano、Michikazu Yoshioka

  DOI：10.1016/s0040-4039(01)01443-5

  日期：2001.10

  2,2,4,4.6,6-Hexamethyl-1.3,5-trithia- and 1,3,5-triselena-2,4,6-tristannins reacted with 2,4,6-tri-t-butylbenzonitrile oxide to give 2,2-dimethyl-1,3-oxathia- and 1,3,5,2-oxaselenazastannoles. The reaction of 2,2,4,4-tetra-t-butyl-1,3,2,4-dithiadistannetane with 2,4,6-tri-t-butylbenzonitrile oxide gave 2,2-di-t-butyl-1,3,5,2-oxathiazastannole. The unusual thermal behavior of the oxachalcogenazastannole is also described. (C) 2001 Elsevier Science Ltd. All rights reserved.