2-(5-methoxy-1H-indol-3-yl)ethanal | 22139-72-6

• 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
• 英文名称: 2-(5-methoxy-1H-indol-3-yl)ethanal
• 英文别名: 5-methoxyindole-3-acetaldehyde；3-Formylmethyl-5-methoxy-indol；1H-Indole-3-acetaldehyde, 5-methoxy-；2-(5-methoxy-1H-indol-3-yl)acetaldehyde
• CAS: 22139-72-6
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: XVHHCGDXCDKKLH-UHFFFAOYSA-N

物化性质

• 沸点：
  388.9±27.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-methoxy-1H-indol-3-yl)ethanal 在 bismuth(lll) trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 32.0h， 生成 (Z)-ethyl 2-(1-((4-chlorophenyl)imino)-6-methoxy-1,3,4,9-tetrahydrothiopyrano[3,4-b]indol-3-yl)acetate
  参考文献：
  名称：

  通过Bi（OTf）3-催化的串联Friedel-Crafts烷基化/ Thia-Michael加成反应快速地一锅获得独特的3,4-二氢硫代吡喃并[3,4-b]吲哚-1（9H）-亚胺

  摘要：

  已经开发了一种有趣的新途径，可通过串联的Friedel-Crafts烷基化反应和Thia-Michael加成反应获得3,4-二氢硫代吡喃并[3,4- b ]吲哚-1（9 H）-亚胺。此外，所描述的方法学也适用于研究较少的四氢-1 H - thiepino [3,4- b ]吲哚支架。该策略以原子经济，各种官能团耐受性和广泛的底物范围为关键特征。

  DOI：

  10.1002/ejoc.201801012
• 作为产物：
  描述：

  DL-5-甲氧基色氨酸 在 sodium hypochlorite 作用下， 以 水 、 甲苯 为溶剂， 以34%的产率得到2-(5-methoxy-1H-indol-3-yl)ethanal
  参考文献：
  名称：

  Synthesis and Preliminary Pharmacological Evaluation of 4′-Arylalkyl Analogues of Clozapine. II. Effect of the Nature and Length of the Linker

  摘要：

  我们报告了氯氮平第二代三环类似物的合成，研究了在生理 pH 值下可电离的氮原子与引入的芳基之间链条的长度和性质。本文介绍了这一系列氯氮平 4′-芳基烷基类似物的化学、结构特征和药理学评价。研究讨论了链接物的性质和长度、不饱和度以及芳基类型对多巴胺 D4 和血清素 5-HT2A 受体阻断活性影响的初步发现，并提供了主要化合物的动物行为数据。

  DOI：

  10.1071/ch03030

文献信息

• A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues
  作者：Chou-Hsiung Chen、Sivaneswary Genapathy、Peter M. Fischer、Weng C. Chan

  DOI：10.1039/c4ob02107j

  日期：——

  A facile route has been established for the synthesis of indole-substituted (S)-tryptophans from corresponding indoles, which utilizes a chiral auxiliary-facilitated Strecker amino acid synthesis strategy. The chiral auxiliary reagents evaluated were (S)-methylbenzylamine and related derivatives. To illustrate the robustness of the method, eight optically pure (S)-tryptophan analogues were synthesized

  已经建立了从相应的吲哚合成吲哚取代的（S）-色氨酸的简便路线，该路线利用了手性辅助促进的Strecker氨基酸合成策略。评价的手性辅助试剂是（S）-甲基苄胺和相关衍生物。为了说明该方法的鲁棒性，合成了八个光学纯的（S）-色氨酸类似物，随后将其用于有效的抗菌剂精氨酸A及其类似物的会聚合成。
• Stereospecific access to bridged [n.2.1] skeletons through gold-catalyzed tandem reaction of indolyl homopropargyl amides
  作者：Tong-De Tan、Xin-Qi Zhu、Mei Jia、Yongjia Lin、Jun Cheng、Yuanzhi Xia、Long-Wu Ye

  DOI：10.1016/j.cclet.2019.10.019

  日期：2020.5

  cycloisomerization-initiated tandem reaction of Boc-protected indole tethered homopropargyl amides has been achieved. This method delivers a wide range of valuable bridged aza-[n.2.1] skeletons (n = 3–7) at room temperature with high diastereoselectivity and enantioselectivity by a chirality-transfer strategy. Moreover, the gold-catalyzed tandem reaction of homopropargyl alcohol is also achieved to produce

  摘要实现了由Boc保护的吲哚链式均炔丙基酰胺的高效金催化抗马氏复合环引发的串联反应。该方法可通过手性转移策略在室温下提供多种有价值的桥连氮杂[n.2.1]骨架（n = 3-7），具有高非对映选择性和对映选择性。此外，还实现了金炔丙醇的串联催化反应，以生产桥联的氧杂-[3.2.1]骨架。
• [EN] CATALYTIC TRYPTAMINE PROCESSES AND PRECURSORS<br/>[FR] PROCÉDÉS ET PRÉCURSEURS DE TRYPTAMINE CATALYTIQUES
  申请人：KARE CHEMICAL TECH INC

  公开号：WO2022232931A1

  公开（公告）日：2022-11-10

  The present disclosure relates to the use of tryptamine precursor compounds and zinc amide enolate compounds for the preparation of tryptamines. The disclosure also relates to the use of catalysts and catalytic processes for the preparation of tryptamines using the zinc amide enolate compounds and the tryptamine precursor compounds.

  本公开涉及使用色胺前体化合物和锌酰胺烯醇化合物制备色胺。该公开还涉及使用催化剂和催化过程，使用锌酰胺烯醇化合物和色胺前体化合物制备色胺。
• 一类吲哚乙基氟硼酸衍生物及其制备方法和用途
  申请人：复旦大学

  公开号：CN115772183A

  公开（公告）日：2023-03-10

  本发明属医药技术领域，涉及如式I所示吲哚乙基氟硼酸衍生物物及其制备方法和用途，具体涉及一类吲哚乙基氟硼酸衍生物及其制备方法和在制药中的用途，尤其是在制备以肿瘤IDO1、TDO和IDO2为作用靶点的肿瘤诊断与治疗药物中的应用。本发明所述化合物具有IDO1、IDO2或/和TDO抑制活性，可制成肿瘤免疫治疗药物；利用式I化合物具有的靶向性，通过F‑18标记，可制成PET显像剂用于肿瘤诊断；利用所含硼原子，可制成硼中子捕获放射治疗药物制品，进一步达到临床诊疗一体化的目的。
• Substrate-specific enhancement of the oxidative half-reaction of monoamine oxidase
  作者：Anthony K. Tan、Rona R. Ramsay

  DOI：10.1021/bi00060a003

  日期：1993.3.9

  Monoamine oxidases A and B have identical flavin sites but different, although overlapping, amine substrate specificity. Reoxidation of ternary complexes containing substrate is much faster than of free enzyme, and the enhancement is greater in the A form than the B form. The oxidative half-reaction was studied with a variety of substrates to elucidate the specificity of the effect and to probe the different influences of substrate on the flavin reoxidation in the two forms of the enzyme. The second-order rate constant for the reoxidation was highest with monoamine oxidase A when kynuramine was the ligand (508 x 10(3) M-1 s-1) compared to 4 x 10(3) M-1 s-1 in its absence. MPTP (166 x 10(3) M-1 s-1) also enhanced reoxidation well, but indole substrates stimulated only poorly (e.g., tryptamine, 29 x 10(3) M-1 s-1; serotonin, 50 x 10(3) M-1 s-1). For the A form, the reduction of the flavin was rate-limiting in all cases. For the B form, reoxidation was rate-limiting for beta-phenylethylamine and contributed to the determination of the overall rate with several substrates. The ratio of the enhanced rate of oxidation to the rate of reduction correlated with the redox state of the enzyme in turnover experiments. All the observations are consistent with alternate paths of reoxidation, via either free enzyme or a reduced enzyme-substrate complex. The flux through each path is determined by the relative dissociation constants and rate constants.