1-Diazotetralin | 107820-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-Diazotetralin
• 英文别名: 1-diazo-1,2,3,4-tetrahydronaphthalene；Naphthalene, 1-diazo-1,2,3,4-tetrahydro-；4-diazo-2,3-dihydro-1H-naphthalene
• CAS: 107820-92-8
• 化学式: C₁₀H₁₀N₂
• 分子量: 158.203
• InChiKey: SFPIWFSIABZJCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Diazotetralin 在 铜 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 18.0h， 生成 (10R,11R,P)-10,11-diethyl-5-(1,2,3,4-tetrahydro-1-naphthalenyliden)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene
  参考文献：
  名称：

  C₂-Symmetric Dibenzosuberane-Based Helicenes as Potential Chirochromic Optical Switches

  摘要：

  Three C-2-symmetric (10R,11R)-diethyl substituted dibenzosuberane (DBS)-based helicenes with varying steric and conjugation demands of their bottom fragments were synthesized. The X-ray analyses of their precursors-episulfides reveal the preferred conformation of the DBS skeleton possessing equatorially oriented ethyl groups at C-8 and C-9 positions. In all cases, the absolute configuration in the episulfide moiety is S, which can lead stereospecifically to the corresponding P helicenes after the reductive desulfurization of the episulfides. Only the helicene 7a with the bottom part derived from alpha-tetralone was found photoswitchable in reasonable time scale. Photoisomerization of the diastereomerically pure (10R,11R,P)-helicene (7a) at 280 nm led to virtually exclusive formation of the opposite M form-diastereomer 7a' (7a'/7a = 99.6/0.4). The preferential return of 7a' to 7a can be effected upon irradiation at 254 nm (7a'/7a = 33/67) or thermally at 130 degrees C (7a'/7a = 0/100). The photoinduced switching process amounts to a 133% difference in de (from 99.2% to -34%). The concomitant change of helicene chirality between these two diastereomeric photostationary states augurs well for their potential application as an optical switch in LC materials. To our knowledge, our system serves as the best chirochromic optical switch as compared to the examples possessing similar photochromic properties.

  DOI：

  10.1021/ja993297d
• 作为产物：
  描述：

  1-tetralone hydrazone 在 正丁基锂 、 azidophosphonium bromide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以90%的产率得到1-Diazotetralin
  参考文献：
  名称：

  正丁基锂和叠氮（二乙氨基）phosph将of转化为重氮化合物

  摘要：

  由与正丁基锂/己烷在-78°C下于THF反应制得的酰肼锂在约0°C下于THF中由叠氮基（二乙基氨基）efficiently有效，快速，安全地转化为相应的重氮化合物与三（二乙氨基）磷亚胺，氮和溴化锂。

  DOI：

  10.1016/s0040-4039(02)01443-0

文献信息

• Quinoxaline-fused dibenzosuberane based helicenes and organic electroluminescent device using the same
  申请人：JUST ABOUT SHOWING CO., LTD.

  公开号：US10040772B1

  公开（公告）日：2018-08-07

  A quinoxaline-fused dibenzosuberane based helicene is shown in formula (1), wherein A is with a structure of formula (2), formula (3a) or formula (3b); X is an oxygen atom, sulfur atom, amino group, or —(CH2)n, wherein n is 0, 1, or 2; R1 and R2 are independently selected from the group consisting of hydrogen atom, halogen atom, formula (4), formula (5) and formula (6); and R3 to R15 are independently selected from the group consisting of hydrogen atom, halogen atom, cyano group, alkyl group, cycloalkyl group, alkoxy group, thioalkyl group, silyl group, alkenyl group, aryl group, heteroaryl group, and amino group.

  一个以喹喔啉融合的二苯并二环戊烷为基础的螺环化合物如公式（1）所示， 其中A具有公式（2）、公式（3a）或公式（3b）的结构； X为氧原子、硫原子、氨基或—(CH2)n，其中n为0、1或2； R1和R2分别选自氢原子、卤原子、公式（4）、公式（5）和公式（6）的基团； R3至R15分别选自氢原子、卤原子、氰基、烷基、环烷基、烷氧基、硫代烷基、硅烷基、烯基、芳基、杂环芳基和氨基的基团。
• Safe and Facile Access to Nonstabilized Diazoalkanes Using Continuous Flow Technology
  作者：Pauline Rullière、Guillaume Benoit、Emmanuelle M. D. Allouche、André B. Charette

  DOI：10.1002/anie.201802092

  日期：2018.5.14

  potential of nonstabilized diazo compounds, their utilization has always been hampered by stability, toxicity, and safety issues. The present method opens up access to the most reactive nonstabilized diazoalkanes. Among diazo compounds, nonstabilized alkyl diazo compounds are the least represented because of their propensity to degrade during preparation. The continuous flow oxidation process of hydrazones

  尽管不稳定的重氮化合物具有很高的合成潜力，但其使用一直受到稳定性，毒性和安全性问题的阻碍。本方法打开了反应性最强的不稳定的重氮烷烃的途径。在重氮化合物中，不稳定的烷基重氮化合物代表最少，因为它们在制备过程中易于降解。oxide在氧化银柱上的连续流动氧化过程提供了不含碱和金属的纯重氮二氯甲烷溶液的输出物流。从无毒的酮和醛开始，这种方法可以以优异的收率生产各种前所未有的重氮烷烃化合物，同时突出了其合成潜力和安全大规模重氮生产的可能性。
• Decomposition of toluene-p-sulphonylhydrazones by alkali. Part II
  作者：R. K. Bartlett、T. S. Stevens

  DOI：10.1039/j39670001964

  日期：——

  Hydrazones of further mono- and especially di-carbonyl compounds have been studied. That of acetonylacetone gave hexa-2,5-diene, and that of biphenacyl gave diphenylbutadiene with much 3,6-diphenylpyridazine. Hydrazones of αβ-unsaturated aldehydes and ketones gave pyrazoles, also obtained under the same conditions from 1-toluenesulphonylpyrazolines. Hydrazones of ω-substituted acetophenones, PhCO·CH2X

  已经研究了其他单羰基化合物，尤其是二羰基化合物的dra。丙酮基丙酮的化合物得到六-2，5-二烯，而联苯酰基基的化合物得到具有大量3，6-二苯基哒嗪的二苯基丁二烯。αβ-不饱和醛和酮的gave得到吡唑，也以相同条件从1-甲苯磺酰基吡唑啉获得吡唑。ω-取代的苯乙酮的CO（PhCO·CH 2 X）产生苯乙酮以及PhCH·CHX（X = OR或Ts）。
• Enantioselective Synthesis of Trisubstituted Allenes via Cu(I)-Catalyzed Coupling of Diazoalkanes with Terminal Alkynes
  作者：Wen-Dao Chu、Lei Zhang、Zhikun Zhang、Qi Zhou、Fanyang Mo、Yan Zhang、Jianbo Wang

  DOI：10.1021/jacs.6b09674

  日期：2016.11.9

  A highly enantioselective synthesis of trisubstituted allenes has been achieved through Cu(I)-catalyzed cross-coupling of aryldiazoalkanes and terminal alkynes with chiral bisoxazoline ligands. Alkynyl migratory insertion of Cu(I) carbene is proposed as the key step for the construction of axial chirality.

  通过 Cu(I) 催化的芳基重氮烷烃和末端炔烃与手性双恶唑啉配体的交叉偶联，实现了三取代丙二烯的高度对映选择性合成。Cu（I）卡宾的炔基迁移插入被认为是构建轴向手性的关键步骤。
• 1,2-Hydrogen migration and alkene formation in the photoexcited states of alkylphenyldiazomethanes
  作者：Sol Celebi、Soccoro Leyva、David A. Modarelli、Matthew S. Platz

  DOI：10.1021/ja00072a014

  日期：1993.9

  Laser flash photolysis of alkylphenyldiazomethanes in the presence of pyridine produces easily detected ylides. The data indicate that photolysis of alkylphenyldiazomethanes leads to both carbene formation and direct formation of rearrangement products which do not derive from relaxed carbene intermediates

  在吡啶存在下，烷基苯基重氮甲烷的激光闪光光解产生易于检测的叶立德。数据表明，烷基苯基重氮甲烷的光解导致卡宾的形成和重排产物的直接形成，这些产物不是来自松弛的卡宾中间体