3-甲氧基-9H-咔唑 | 18992-85-3

• 物质功能分类: 化学农药原药 - 杀菌剂 - 唑类杀菌剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 3-甲氧基-9H-咔唑
• 英文名称: 3-methoxycarbazole
• 英文别名: 3-methoxy-9H-carbazole；3-Methoxy-carbazol
• CAS: 18992-85-3
• 化学式: C₁₃H₁₁NO
• mdl: MFCD00626045
• 分子量: 197.236
• InChiKey: BISIQSCKDZYPLR-UHFFFAOYSA-N

物化性质

• 熔点：
  138-139 °C
• 沸点：
  392.2±15.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  3-甲氧基-9H-咔唑 在 吡啶 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 9H-carbazol-3-yl acetate
  参考文献：
  名称：

  Structure-activity relationship of bromoeudistomin D, a powerful Ca2+ releaser in skeletal muscle sarcoplasmic reticulum

  摘要：

  Bromoeudistomin D and 9-methyl-7-bromoeudistomin D which have a beta-carboline skeleton are powerful Ca2+ releasers from skeletal muscle sarcoplasmic reticulum exhibiting caffeine-like properties. We examined the effects of bromoeudistomin D analogues on Ca(2+)-induced Ca2+ release from skeletal muscle sarcoplasmic reticulum. Among bromoeudistomin D analogues, the Ca(2+)-releasing activities of carboline derivatives were higher than those of carbazole derivatives, suggesting that a carboline skeleton is significantly important for the manifestation of Ca(2+)-releasing activity and Ca2+ sensitivity of Ca(2+)-induced Ca2+ release. On the contrary, the analogues which have a carbazole skeleton and bromine at C-6 inhibit both Ca(2+)- and caffeine-induced Ca2+ release. 9-Methyl-substitution of the analogue elevated its Ca(2+)-releasing activity. Moreover, there is a close correlation between the enhancement of [3H]ryanodine binding to sarcoplasmic reticulum by the analogues and the activation of Ca2+ release by them. Bromoudistomin D analogues may provide valuable information about the structure-function relationship of the ryanodine receptor/Ca2+ release channels in skeletal muscle sarcoplasmic reticulum.

  DOI：

  10.1016/0922-4106(95)90040-3
• 作为产物：
  描述：

  3-(4-甲氧基苯基)-[1,2,3]三唑并[1,5-a]吡啶 生成 3-甲氧基-9H-咔唑
  参考文献：
  名称：

  三唑嗪-重氮甲基嗪价异构化。[1,2,3]三唑并[1,5- a ]吡啶和2-重氮甲基吡啶

  摘要：

  [1-2,3]三唑并[1,5- a ]吡啶1T和6T的价异构体2-重氮甲基吡啶1D和6D已通过温和的快速真空热解法在约2080 cm –1处直接观察到（ FVP）在200–600°C的温度下进行红外光谱分析。经计算确认约。由[1,2,3]三唑并[1,5- a ]吡啶1T形成2-重氮甲基吡啶1D的17 kcal / mol势垒，重氮化合物约 在三唑之上5 kcal / mol。在较高温度范围（400–600°C）中，2-重氮甲基吡啶1D消除N 2并形成2-吡啶基卡宾2和重排为1-氰基环戊二烯4。2-重氮甲基吡啶1D在20–90°C下与四氰基乙烯（TCNE）进行1,3-偶极环加成反应，生成3-（2-吡啶基）环丙烷四甲腈11和3-（三氰基乙烯基）-[1,2,3]三唑[1] ，5- a ]吡啶13T通过未观察到的吡唑啉10和12。三唑13T的FVP在2080 cm –1处具有对应的重氮化合物13D的IR吸收。

  DOI：

  10.1021/acs.joc.5b02639

文献信息

• The reactions of some tetrahydro-β-carbolines, of hexahydroazepino[3,4-b]indoles, and of tetrahydrocarbazolones with arenesulphonyl azides
  作者：A. Sydney Bailey、Marazban H. Vandrevala

  DOI：10.1039/p19800001512

  日期：——

  9-dimethyl-1,2,3,4-tetrahydro-β-carboline react with arenesulphonyl azides forming indoline-3-spiropyrrolidines; 2,10-dimethyl-3,4,5,10-tetrahydroazepino[3,4-b]indol-1 (2H)-one and 2,10-dimethyl-1,2,3,4,5,10-hexahydroazepino[3,4-b]indole react to form indoline-3-spiropiperidines. 9-Methyl-2-oxo-tetrahydrocarbazole reacts with p-chlorobenzenesulphonyl azide to form 1-methyl-2-p-chlorophenylsulphonylimino

  2,9-二甲基-1,2,3,4-四氢-1-氧代-β-咔啉和2,9-二甲基-1,2,3,4-四氢-β-咔啉与芳磺酰叠氮化物反应形成二氢吲哚- 3-螺吡咯烷; 2,10-二甲基-3,4,5,10-四氢氮杂环庚烷[3,4- b ]吲哚-1（2 H）-one和2,10-二甲基-1,2,3,4,5,10-六氢氮杂环庚烷[3,4- b ]吲哚反应形成吲哚啉-3-螺哌啶。9-甲基-2-氧代-四氢咔唑与对氯苯磺酰基叠氮化物反应形成1-甲基-2-对氯苯磺酰氨基-3'-氧代吲哚-3-螺旋环戊烷。
• Enantioconvergent Alkylations of Amines by Alkyl Electrophiles: Copper-Catalyzed Nucleophilic Substitutions of Racemic α-Halolactams by Indoles
  作者：Agnieszka Bartoszewicz、Carson D. Matier、Gregory C. Fu

  DOI：10.1021/jacs.9b07875

  日期：2019.9.18

  classic SN2 reaction of an amine with an alkyl electrophile, both with respect to reactivity and to enantioselectivity. In this study, we describe the development of a user-friendly method (reaction at room temperature, with commercially available catalyst components) for the enantioconvergent nucleophilic substitution of racemic secondary alkyl halides (α-iodolactams) by indoles. Mechanistic studies are

  过渡金属催化有可能解决胺与烷基亲电试剂的经典 SN2 反应在反应性和对映选择性方面的缺点。在这项研究中，我们描述了一种用户友好的方法（在室温下反应，与市售的催化剂组分）的开发，用于由吲哚对外消旋仲烷基卤化物（α-碘内酰胺）的对映聚合亲核取代。机理研究与铜 (I)-吲哚基复合物的形成一致，该复合物与亲电子试剂的两种对映异构体以不同的速率反应，它们在反应条件下相互转化（动态动力学拆分）。这项研究补充了早期光诱导对映会聚 N-烷基化的工作，
• Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids
  作者：Bhakti A. Dalvi、Pradeep D. Lokhande

  DOI：10.1016/j.tetlet.2018.01.061

  日期：2018.5

  protocol for the aromatization of tetrahydrocarbazole is described by using catalytic copper(II) chloride dihydrate in DMSO. This newly established methodology has utilized towards the synthesis of naturally occurring carbazole alkaloids, namely 3-methylcarbazole, 3-formyl carbazole, glycozoline, glycozolicine and clauszoline-K. In addition, the protocol is generalized for the aromatization of N-substituted

  通过在二甲基亚砜中使用催化氯化铜（II）二水合物描述了一种有效的四氢咔唑芳构化方案。这种新近建立的方法已经用于合成天然存在的咔唑生物碱，即3-甲基咔唑，3-甲酰基咔唑，糖唑啉，糖唑啉和clauszoline-K。另外，该方案被普遍用于N-取代的四氢咔唑，1,2,3,4-四氢喹啉，1,2,3,4-四氢异喹啉和1,2,3,4-四氢β-咔啉的芳构化，从而得到相应的杂芳族化合物从非常好的收率到优异的收率。此外，已证明该方法可耐受多种官能团，并具有优异的收率。
• Transition‐Metal‐Catalyzed Alkylations of Amines with Alkyl Halides: Photoinduced, Copper‐Catalyzed Couplings of Carbazoles
  作者：Alex C. Bissember、Rylan J. Lundgren、Sidney E. Creutz、Jonas C. Peters、Gregory C. Fu

  DOI：10.1002/anie.201301202

  日期：2013.5.3

  N‐alkylations of carbazoles with a variety of secondary and hindered primary alkyl iodides can be achieved by using a simple precatalyst (CuI) under mild conditions (0 °C) in the presence of a Brønsted base; at higher temperature (30 °C), secondary alkyl bromides also serve as suitable coupling partners. A Li[Cu(carbazolide)2] complex has been crystallographically characterized, and it may serve as

  在温和的条件下（0°C），在布朗斯台德碱的存在下，使用简单的预催化剂（CuI）可以实现咔唑与各种仲烷基和受阻伯烷基碘的N-烷基化反应。在较高温度（30°C）下，仲烷基溴化物也可以用作合适的偶合伴侣。Li [Cu（咔唑化物）2 ]络合物已经在晶体学上进行了表征，并且它可以用作催化循环中的中间体。
• Heterogeneous photocatalysis of azides: extending nitrene photochemistry to longer wavelengths
  作者：Ignacio D. Lemir、Juan E. Argüello、Anabel E. Lanterna、Juan C. Scaiano

  DOI：10.1039/d0cc04118a

  日期：——

  The photodecomposition of azides to generate nitrenes usually requires wavelengths in the <300 nm region. In this study, we show that this reaction can be readily performed in the UVA region (368 nm) when catalyzed by Pd-decorated TiO2. In aqueous medium the reaction leads to amines, with water acting as the H source; however, in non-protic and non-nucleophilic media, such as acetonitrile, nitrenes

  叠氮化物的光分解以生成腈通常需要在<300 nm范围内的波长。在这项研究中，我们表明当由Pd装饰的TiO 2催化时，该反应可以在UVA区域（368 nm）中轻松进行。在水介质中，反应生成胺，水作为H源。然而，在非质子和非亲核介质（如乙腈）中，氮烯会重组生成偶氮化合物，而在亲核试剂存在下会发生叠氮基介导的捕获。非均相过程有助于催化剂分离，同时显示出高的化学选择性和高产率。

表征谱图