3-azido-1H-indene | 16719-57-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 3-azido-1H-indene
• 英文别名: 1-azidoindene；3-azidoindene；1-Azido-inden；1-Azidoinden；1H-Indene, 3-azido-
• CAS: 16719-57-6
• 化学式: C₉H₇N₃
• 分子量: 157.175
• InChiKey: QDVRINRDDBOJAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-azido-1H-indene 生成 2-溴-1-茚满酮
  参考文献：
  名称：

  Stereochemistry. LXV. Mechanism of interaction of vinyl azides with electrophilic bromine

  摘要：

  DOI：

  10.1021/ja00750a027
• 作为产物：
  描述：

  1-azido-2-iodo-2,3-dihydro-1H-indene 在 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 3-azido-1H-indene
  参考文献：
  名称：

  Rh-Cu双金属配合物由α-芳基乙烯基叠氮化物和内部炔烃合成异喹啉

  摘要：

  继电器中的催化剂：已开发出一种用于合成高度取代的异喹啉的合成方法（参见方案; Cp * = C 5 Me 5，DMF = N，N-二甲基甲酰胺，TEMPO = 2,2,6,6-四甲基哌啶-1-氧基）。初步的机理研究表明，铑和铜在多步骤序列中协同协同作用。

  DOI：

  10.1002/anie.201101009

文献信息

• PhI(OAc)₂-Mediated Radical Trifluoromethylation of Vinyl Azides with Me₃SiCF₃
  作者：Yi-Feng Wang、Geoffroy Hervé Lonca、Shunsuke Chiba

  DOI：10.1002/anie.201307846

  日期：2014.1.20

  and functional materials, owing to its unique properties such as electron‐withdrawing character, metabolic stability, and lipophilicity. Described herein is the PhI(OAc)2‐mediated radical trifluoromethylation of vinyl azides with Me3SiCF3 to efficiently generate α‐trifluoromethyl azines. The resulting α‐trifluoromethyl azines were successfully transformed to valuable fluorine‐containing molecules such

  含氟有机基序由于其独特的特性，例如吸电子特性，代谢稳定性和亲脂性，在制药，农用化学品和功能材料中正变得尤为重要。本文描述的是用Me 3 SiCF 3进行的叠氮化物的PhI（OAc）2介导的自由基三氟甲基化反应，可有效地生成α-三氟甲基嗪。所得的α-三氟甲基嗪已成功转化为有价值的含氟分子，例如α-三氟甲基酮，β-三氟甲基胺，5-氟吡唑和三氟乙基异喹啉。
• On the reaction of (vinylimino)phosphoranes and related compounds. A short new synthesis of 5-azaazulene derivatives
  作者：Makoto Nitta、Yukio Iino、Satoshi Mori

  DOI：10.1016/s0040-4039(00)93587-1

  日期：1991.11

  The facile synthesis of phenyl-substituted and condenced 5-azaazulene ring systems was accomplished by the reaction of 2-formyl-6-dimethylaminofulvene with several phenyl-substituted (vinylimino)phosphoranes in one-flask operation.

  通过在一个烧瓶操作中使2-甲酰基-6-二甲基氨基富勒烯与数个苯基取代的（乙烯基酰亚胺）磷杂环戊烷反应来完成苯基取代的和稠合的5-氮杂氮烯环系统的简便合成。
• On the reactions of (vinylimino)phosphoranes and related compounds. Part 30. Short new synthesis of 5-azaazulene derivatives. Some comments on reactivities of (vinylimino)phosphoranes
  作者：Makoto Nitta、Yukio Iino、Satoshi Mori、Tohru Takayasu

  DOI：10.1039/p19950001001

  日期：——

  A short new synthesis of phenyl-substituted and annulated 5-azaazulene (cyclopenta[c]azepine) derivatives 15–18 consists of the reaction of [(1-phenylvinyl)imino]- and benz-annulated [(cycloalkenyl)imino]-phosphoranes 8–11 with 5-(dimethylaminomethylene)cyclopenta-1,3-dienecarbaldehyde 1 in an enamine alkylation (Michael addition) process, subsequent proton migration–ketonization, and condensation

  苯基取代的和环化5- azaazulene（环戊二烯并[的简短新合成Ç ]氮杂）衍生物15 - 18由[（1-苯基乙烯基）亚氨基]的反应的-和苯并-环[（环烯基）亚氨基] -phosphoranes 8 - 11 5-（二甲氨基亚甲基）环戊二烯基-1,3- dienecarbaldehyde 1中的烯胺烷基化与所述膦亚胺部分（氮杂Wittig反应）的甲酰基的（迈克尔加成）处理，随后的质子迁移酮化，并冷凝。在另一方面，醛的反应1与（vinylimino）正膦12 - 14，其具有在相对于氮原子的α位没有苯基，由一个分子内氮杂Wittig反应或醛的取代反应的1与正膦12 - 14和随后水解，得到5-（氨基亚甲基）环戊二烯-1- ，3-二烯甲醛19及其衍生物20和21。在选择性的上下文中膦的反应观察到的8 - 11和12 - 14用醛1，分别对化合物MNDO计算1和12A，12B以及在模型化合物8C
• Banert, Klaus; Hagedorn, Manfred; Liedtke, Christine, European Journal of Organic Chemistry, 2000, # 2, p. 257 - 267
  作者：Banert, Klaus、Hagedorn, Manfred、Liedtke, Christine、Melzer, Antje、Schoeffler, Claudia

  DOI：——

  日期：——
• On the reaction of (vinylimino)phosphorane and related compounds. 22. Syntheses and structural studies of methanocycloundeca[b]pyrrole ring systems
  作者：Nobuhiro Kanomata、Kenichi Kamae、Yukio Iino、Makoto Nitta

  DOI：10.1021/jo00046a010

  日期：1992.9

  Novel 2-phenyl-6,11- and 2-phenyl-4,9-methanocycloundeca[b]pyrroles (15a and 16a) were synthesized in moderate yields by the reaction of 3,8-methano[11]annulenone (3), a 10pi-electron vinylogue of tropone, with [(l-phenylvinyl)imino]triphenylphosphorane (8a) and subsequent dehydrogenation. Similarly, the reaction of the annulenone 3 with (inden-3-ylimino)tributylphosphorane (8c) and subsequent aromatization afforded 7,12- and 9,14-methano-15H-cycloundeca[b]indeno[2,3-d]pyrroles (15c and 16c), which also have methanocycloundeca[b]pyrrole ring systems. Preparation of 2-phenyl-5,10-methanocycloundeca[b]pyrrole (17), an isomer of both 15a and 16a, was also accomplished in low yield by the reaction of 4,9-methano[ll]annulenone (5) with an excess of [(1-phenylvinyl)imino]tributylphosphorane (8d). The reactivity of annulenone 5 with (vinylimino)phosphoranes was found to be quite low as compared to the higher reactivity of annulenone 3 and tropone. Compounds 15a,c, 16a,c, and 17 are the first nitrogen analogues of cyclopentacycloundecene ring systems which have vinylogous structures of 1-azaazulene. Structures of the products obtained were examined by H-1 NMR spectra and UV spectra. The H-1 NMR spectra clarified that the compounds 15a,c, 16a,c, and 17 are aromatic molecules having a diatropic 14pi-electron system, and 5,10-methano derivative 17 has a more diatropic nature than the compounds 15a,c and 16a,c. The UV spectra of 15a,c, 16a,c, and 17 exhibited increased cyclic conjugation of the aromatic perimeter according to a bathochromic shift of the longest absorption maxima as compared to the corresponding 1-azaazulene derivatives.