diazido(4-methoxyphenyl)methane | 92567-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diazido(4-methoxyphenyl)methane
• 英文别名: 1-(diazidomethyl)-4-methoxybenzene
• CAS: 92567-07-2
• 化学式: C₈H₈N₆O
• 分子量: 204.191
• InChiKey: JTLSRCHNVXCKPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  106.75
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  diazido(4-methoxyphenyl)methane 在 碘苯二乙酸 作用下， 以 乙腈 为溶剂， 以57%的产率得到4-甲氧基苯甲腈
  参考文献：
  名称：

  室温下将甲基芳烃直接转化为芳基腈

  摘要：

  在温和和中性条件下，甲基芳烃直接转化为芳基腈时，三个CH键被裂解（参见方案）。这种新的合成工具不仅可用于构建合成和医学上重要的芳基腈，而且还可以在温和的条件下实现CH官能化。PIDA ＝苯基乙酸二乙酸铵。

  DOI：

  10.1002/anie.200903838
• 作为产物：
  描述：

  1-(Diazonioiminomethyl)-4-methoxybenzene 在 高氯酸 、 水 作用下， 以 乙腈 为溶剂， 生成 diazido(4-methoxyphenyl)methane
  参考文献：
  名称：

  Richard, John P.; Amyes, Tina L.; Jagannadham, Vandanapu, Journal of the American Chemical Society, 1995, vol. 117, # 19, p. 5198 - 5205

  摘要：

  DOI：

文献信息

• Reactions of trimethylsilyl azide with aldehydes: facile and convenient syntheses of diazides, tetrazoles, and nitriles
  作者：Kozaburo Nishiyama、Makoto Oba、Akio Watanabe

  DOI：10.1016/s0040-4020(01)90003-1

  日期：——

  The reactions of trimethylsilyl azide (TMSA) with various aldehydes were found to be versatile procedures for the synthesis of gem- and 1,3-diazides, tetrazoles, and nitriles, whose formation was varied by controlling the quantities of TMSA, catalyst, and the reaction conditions.

  发现叠氮化三甲基甲硅烷基（TMSA）与各种醛的反应是合成宝石-和1,3-二叠氮化物，四唑和腈的通用方法，通过控制TMSA，催化剂和二甲基亚砜的量可以改变它们的形成。反应条件。
• Trapping of Azidocarbenium Ion: A Unique Route for Azide Synthesis
  作者：Suman Pramanik、Prasanta Ghorai

  DOI：10.1021/ol5008235

  日期：2014.4.18

  the first time, a sensitive azidocarbenium ion intermediate has been trapped with various nucleophiles to provide azides in excellent chemoselectivity. This provides a novel approach for the chemoselective synthesis of primary and secondary benzyl azides from aldehydes in a one-pot reaction. Enantioselective nucleophilic addition to the azidocarbenium ion has also been initiated.

  首次将敏感的叠氮碳鎓离子中间体与各种亲核试剂一起捕获，以提供具有出色化学选择性的叠氮化物。这提供了一种通过一锅法从醛化学选择性合成伯和仲苄基叠氮化物的新方法。对叠氮碳鎓离子的对映选择性亲核加成反应也已经开始。
• An Efficient and Tunable Route to Bis(1,2,3-triazol-1-yl)methane-Based Nitrogen Compounds
  作者：José A. Castro-Osma、Agustín Lara-Sanchez、Antonio Otero、Ana M. Rodríguez、María C. de la Torre、Miguel A. Sierra

  DOI：10.1002/ejoc.201501519

  日期：2016.2

  compounds. Thus, the preparation of new bis(1,2,3-triazol-1-yl)methane-based heteroscorpionate neutral precursors pbptztamH (10), pbttztamH (11), (S)-mbptzamH (12) and (S)-mbttzamH (13) and a dinuclear zinc complex, [Znpbptztam}Et]2 (14), was achieved. The structures of the compounds were determined by spectroscopic methods, and the X-ray crystal structures of compounds 2, 3, 7, 8, 9 and 14 were established

  一种新的简单方法来制备“点菜”双（1,2,3-三唑-1-基）甲烷化合物，即 bmtzm (1)、bptzm (2)、bttzm (3)、bmtzpm (4)、报告了具有不同官能团的 bptzpm (5)、bttzpm (6)、bmtzom (7)、bptzom (8) 和 bttzom (9)。这些化合物是通过容易获得的炔烃和孪晶二叠氮化物在双铜催化的叠氮化物-炔烃环加成 (CuAAC) 反应中反应制备的。这些材料被用作合成更复杂化合物的起始材料。因此，制备新的双（1,2,3-三唑-1-基）甲烷基杂蝎酸盐中性前体 pbptztamH (10)、pbttztamH (11)、(S)-mbptzamH (12) 和 (S)-mbttzamH (13) 和双核锌络合物，[Znpbptztam}Et]2 (14)，得到了。化合物的结构由光谱法确定，
• The effects of .alpha.-substituents on the kinetic and thermodynamic stability of 4-methoxybenzyl carbocations: carbocation lifetimes that are independent of their thermodynamic stability
  作者：Tina L. Amyes、Ishmael W. Stevens、John P. Richard

  DOI：10.1021/jo00074a036

  日期：1993.10

  The following new rate constants for reaction of alpha-substituted 4-methoxybenzyl carbocations, 4-MeOC6H4CR1(R2)+, With a solvent of 50:50 (v/v) trifluoroethanol/water at 25-degrees-C and ionic strength 0.50 (NaClO4) are reported: 4-MeOC6H4CH(OMe)+, k(S) = 2.2 X 10(7) s-1; 4-MeOC6H4CH(N3)+, k(S) = 3.3 X 10(5) s-1; 4-MeOC6H4C(CH3)2+, k(S) = 1.3 x 10(7) s-1; 4-MeOC6H4CH(CO2Et)+, k(S) = 1.4 X 10(7) s-1; 4-MeOC6H4CCH3(CF3)+, k(S) = 2.5 x 10(7) s-1. The values of k(S) for reaction of 4-MeOC6H4CR1(R2)+ with 50:50 (v/v) trifluoroethanol/water are nearly independent of very large changes in the thermodynamic stability of these carbocations caused by the addition of a wide range of electron-withdrawing or electron-donating groups at the alpha-position. In the most extreme case, the change from an alpha-methoxy to two alpha-(trifluoromethyl) substituents leads to a 23 kcal/mol thermodynamic destabilization of 4-MeOCrH4CR1(R2)+ relative to the neutral azide ion adducts but a 5-fold decrease in its reactivity toward solvent. The data show that the effects of alpha-substituents on the kinetic stability of 4-MeOC6H4CR1(R2)+ are complex and do not parallel the thermodynamic stability of these carbocations. The results are explained by consideration of the polar and resonance effects of the alpha-substituents on both the thermodynamic driving force and the intrinsic barrier for capture of the carbocations by solvent. These reactions are a new example of the consequences of the ''principle of nonperfect synchronization''.41
• Jagannadham, Vandanapu; Amyes, Tina L.; Richard, John P., Journal of the American Chemical Society, 1993, vol. 115, # 18, p. 8465 - 8466
  作者：Jagannadham, Vandanapu、Amyes, Tina L.、Richard, John P.

  DOI：——

  日期：——