9-甲基咔唑-1-醇 | 3449-61-4

• 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: 9-甲基咔唑-1-醇
• 英文名称: N-methyl-1-hydroxycarbazole
• 英文别名: 9-methyl-9H-carbazol-1-ol；1-Hydroxy-9-methylcarbazol；9-methyl-carbazol-1-ol；1-Hydroxy-N-methylcarbazole；9-methylcarbazol-1-ol
• CAS: 3449-61-4
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: BCDHBQLNRAQGHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  9-甲基咔唑-1-醇 在 titanium(IV) tetraethanolate 作用下， 以 甲苯 为溶剂， 反应 3.33h， 生成
  参考文献：
  名称：

  Synthesis and Photochromic Behaviour of Novel 2H-1-Benzopyrans (=2H-Chromenes) Derived from Carbazololes

  摘要：

  The synthesis and photochromic properties of new 2,2-diphenyl-2H-1-benzopyrans, fused to an indole moiety, are described. All compounds exhibit photochromic behaviour in solution at room temperature. The heteroanellation effects are variable and depend on the position and geometry of the fused indole moiety. A general bathochromic shift in the spectra of the open forms is observed. The presence of a N-methyl group prevents the broadening of the absorption spectra and promotes the instability of some photoinduced forms of compounds with the indole moiety fused at the 5,6 positions of the 2H-1-benzopyran skeleton. The enhanced photocolouration efficiency in the near-UV and the kinetics of thermal bleaching indicate that the novel compounds with an indole moiety fused at the 6,7 positions, particularly those with a linked thiophene moiety: are very interesting molecules for applications in the field of variable optical absorption systems.

  DOI：

  10.1002/1522-2675(20010516)84:5<1163::aid-hlca1163>3.0.co;2-t
• 作为产物：
  描述：

  benzyl benzyl(2-(1-methyl-1H-indole-2-carbonyl)cyclopropyl)carbamate 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以20%的产率得到9-甲基咔唑-1-醇
  参考文献：
  名称：

  正式的均一纳扎罗夫和活化环丙烷的其他环化反应

  摘要：

  纳扎罗夫对二乙烯基酮的环化作用可得到环戊烯酮。用环丙烷取代乙烯基之一会导致形成正式的正己-纳扎罗夫合成环己烯酮的过程。与纳扎罗夫反应相反，乙烯基环丙基酮的环化是一个逐步过程，通常需要苛刻的条件。本文中，我们描述了两种不同的方法，可进一步极化乙烯基-环丙基酮的三元环，从而在温和的催化条件下进行正式的均一纳扎罗夫反应。在第一种方法中，将酯基α引入到环丙烷的羰基上，反应速率提高了十倍以上，这使我们可以将反应范围扩展到β位置的非电子富芳基供体取代基环丙烷上的羰基。在这种情况下，使用手性路易斯酸催化剂可以实现不对称诱导的原理证明。在第二种方法中，将杂原子（尤其是氮）引入β到环丙烷的羰基上。在这种情况下，当乙烯基被吲哚杂环取代时，反应特别成功。对于游离吲哚，使用铜催化剂观察到了吲哚C3位置的正式均一纳扎罗夫环化反应。相反，使用布朗斯台德酸催化剂观察到在N1位置发生了新的环化反应。两种反应均用于天然生物

  DOI：

  10.1002/chem.201102583

文献信息

• Chemoselective Cross-Coupling between Two Different and Unactivated C(aryl)–O Bonds Enabled by Chromium Catalysis
  作者：Jinghua Tang、Liu Leo Liu、Shangru Yang、Xuefeng Cong、Meiming Luo、Xiaoming Zeng

  DOI：10.1021/jacs.0c00283

  日期：2020.4.29

  combination of low-cost Cr(II) salt, 4,4-di-tert-butyl-2,2-dipyridyl (dtbpy) ligand and magnesium reductant shows high reactivity in promoting the reductive cross-coupling of aryl methyl ether derivatives with aryl esters, by cleavage and coupling of two different C(aryl)-O bonds under mild conditions. The formation of active low-valent Cr species by reduction of CrCl2 with Mg can be considered, which prefers

  我们在这里报告了两个不同且未活化的 C(芳基)-O 键与铬催化之间交叉耦合的第一个例子。低成本的 Cr(II) 盐、4,4-二叔丁基-2,2-二吡啶基 (dtbpy) 配体和镁还原剂的组合在促进芳基甲基醚衍生物与芳基酯，通过在温和条件下裂解和偶联两个不同的 C(芳基)-O 键。可以考虑通过用 Mg 还原 CrCl2 形成活性低价 Cr 物种，它更喜欢在 dtbpy 和邻亚氨基助剂的螯合帮助下最初激活苯基甲基醚的 C(芳基)-O 键。随后的连续还原、第二次 C(芳基)-O 活化和还原消除允许实现 C(芳基)-O/C(芳基)-O 键的选择性交叉偶联。
• Synthesis of 1,2-dioxetanes and intermediates therefor
  申请人：TROPIX, INC.

  公开号：EP0582317A2

  公开（公告）日：1994-02-09

  Compounds having formula (I), wherein T is a polycycloalkylidene group (e.g., adamant-2-ylidene); R is a C₁₋₂₀ alkyl, aralkyl or cycloalkyl group; and Y is a fluorescent chromophore (e.g., m-phenylene), produced by reacting a compound having formula (II) with an R-ylating agent (e.g., R₂SO₄) in the presence of an alkali metal alkoxide in a polar aprotic solvent. Also, compounds having formula (III) are produced by reacting a compound having formula (IV) with formula (V), wherein X is an electronegative leaving group (e.g., a halogen anion such as chloride ion) in the presence of a Lewis base (e.g., a trialkyl-amine) dissolved in an aprotic organic solvent (e.g., benzene or toluene). Also, compounds having formula (VI) are produced by reacting a compound of formula (VII) with a tetra-O-acylated-O-hexopyranoside halide, then hydrolysing off the protective acyl groups. The aforementioned compounds and procedures are useful in the synthesis of enzyme-cleavable 1,2-dioxetane ring systems that can serve as members of a binding pair employed, for example, in chemiluminescent immunoassays, DNA probe assays, and direct assays for an enzyme.

  具有式 (I) 的化合物，其中 T 是亚多环烷基（如亚金刚烷-2-基）；R 是 C₁₋₂₀烷基、芳基或环烷基；以及 Y 是荧光发色团（如间苯二酚）、间苯二酚），通过在极性钝化溶剂中，在碱金属烷氧化物存在下，使具有式（II）的化合物与 R-酰化剂（如 R₂SO₄）反应制得。此外，具有式（III）的化合物是通过具有式（IV）的化合物与式（V）反应制得的，其中 X 为电负性离去基团（如卤素阴离子，如氯离子），反应条件为路易斯碱（如三烷基胺）溶于无极性有机溶剂（如苯或甲苯）中。此外，具有式（VI）的化合物是通过式（VII）的化合物与四-O-酰化-O-吡喃己苷卤化物反应，然后水解掉保护酰基而制得的。上述化合物和程序可用于合成可被酶清除的 1，2-二氧杂环烷环系统，这些环系统可作为例如化学发光免疫测定、DNA 探针测定和酶的直接测定中使用的结合对的成员。
• Method of detecting a substance using enzymatically-induced decomposition of dioxetanes
  申请人：TROPIX, INC.

  公开号：EP0859062A2

  公开（公告）日：1998-08-19

  In an assay method in which a member of a specific binding pair is detected by means of an optically detectable reaction, the improvement wherein the optically detectable reaction includes the reaction, with an enzyme, of a dioxetane having the formula where T is a cycloalkyl or polycycloalkyl group bonded to the 4-membered ring portion of the dioxetane by a spiro linkage; Y is a fluorescent chromophore; X is hydrogen, alkyl, aryl, aralkyl, alkaryl, heteroalkyl, heteroaryl, cycloalkyl, cycloheteroalkyl, or enzyme-cleavable group; and Z is hydrogen or an enzyme-cleavable group, provided that at least one of X or Z must be an enzyme-cleavable group, so that the enzyme cleaves the enzyme-cleavable group from the dioxetane to form a negatively charged substituent bonded to the dioxetane, the negatively charged substituent causing the dioxetane to decompose to form a luminescent substance that includes group Y of said dioxetane.

  在通过光学可检测反应检测特异性结合对成员的检测方法中，改进之处在于其中的光学可检测反应包括具有以下式子的二氧杂环丁烷与酶的反应 其中 T 是环烷基或多环烷基，通过螺连接键与二氧杂环烷的 4 元环部分结合； Y 是荧光发色团； X 是氢、烷基、芳基、芳烷基、烷芳基、杂烷基、杂芳基、环烷基、环杂烷基或酶可裂解基团；和 Z 是氢或酶可切除基团，条件是 X 或 Z 中至少有一个必须是酶可切除基团，以便酶将酶可切除基团从二氧杂环丁烷中切 除，形成与二氧杂环丁烷结合的带负电的取代基，带负电的取代基使二氧杂环丁烷分解，形成包括所述二氧杂环丁烷的 Y 基团的发光物质。
• Kit for conducting an assay to detect a substance using enzymatically-induced decomposition of dioxetanes
  申请人：——

  公开号：US20020102624A1

  公开（公告）日：2002-08-01

  In an assay method in which a member of a specific binding pair is detected by means of an optically detectable reaction, the improvement wherein the optically detectable reaction includes the reaction, with an enzyme, of a dioxetane having the formula 1 where T is a cycloalkyl or polycycloalkyl group bonded to the 4-membered ring portion of the dioxetane by a spiro linkage; Y is a fluorescent chromophore; X is H, alkyl, aryl, aralkyl, alkaryl, heteroalkyl, heteroaryl, cycloalkyl, cycloheteroalkyl, or enzyme-cleavable group; and Z is H or an enzyme-cleavable group, provided that at least one of X or Z must be an enzyme-cleavable group, so that the enzyme cleaves the enzyme-cleavable group from the dioxetane to form a negatively charged substituent bonded to the dioxetane, the negatively charged substituent causing the dioxetane to decompose to form a luminescent substance that includes group Y of said dioxetane.

  在一种检测方法中，通过光学检测反应来检测特异性结合对中的一个成员，其中光学检测反应包括二氧杂环丁烷与酶的反应，其式为 1 其中 T 是通过螺连接键与二氧杂环烷的 4 元环部分结合的环烷基或多环烷基； Y 是荧光发色团； X 是 H、烷基、芳基、芳烷基、烷芳基、杂烷基、杂芳基、环烷基、环杂烷基或酶可裂解基团；和 Z 是 H 或酶可切除基团，条件是 X 或 Z 中至少有一个必须是酶可切除基团，以便酶从二氧杂环丁烷中切 除酶可切除基团，形成与二氧杂环丁烷结合的带负电的取代基，带负电的取代基使二氧杂环丁烷分解，形成包括所述二氧杂环丁烷的 Y 基团的发光物质。
• Light emitting markers for use with substrates
  申请人：——

  公开号：US20030015284A1

  公开（公告）日：2003-01-23

  A method of determining whether a substrate has been subjected to an energy source. In one embodiment, the method includes the steps of providing a polymeric surface, providing a light emitting material having a specified emission spectrum that changes upon exposure to an energy source on the surface or embedded in said substrate and applying said energy source to said surface with said light emitting material. This method can be particularly useful for detecting the bond quality in medical devices.

  一种确定基底是否经受过能量源的方法。在一个实施方案中，该方法包括以下步骤：提供聚合物表面；提供具有特定发射光谱的发光材料，该材料在表面或嵌入所述基底中暴露于能量源后会发生变化；将所述能量源与所述发光材料一起应用于所述表面。这种方法尤其适用于检测医疗设备的粘接质量。