(3-methyl-1H-indol-2-yl)acetic acid methyl ester | 54008-85-4

• 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
• 英文名称: (3-methyl-1H-indol-2-yl)acetic acid methyl ester
• 英文别名: methyl 2-(3-methyl-1H-indol-2-yl)acetate；Methyl-2-<2-(3-methyl)-indol>-acetat；(3-methyl-indol-2-yl)-acetic acid methyl ester
• CAS: 54008-85-4
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: QJMHLTJTFITGIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (3-methyl-1H-indol-2-yl)acetic acid methyl ester 在 咪唑 、 4-二甲氨基吡啶 、 四氧化锇 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 四丁基氟化铵 、 sodium methylate 、 lead(IV) tetraacetate 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 33.67h， 生成
  参考文献：
  名称：

  Alstoscholarisines A–E，单萜吲哚生物碱的合成及其对神经干细胞的调节作用

  摘要：

  已开发出一种多样化的合成策略，用于立体选择性合成alstoscholarisines A–E，单萜类吲哚生物碱，它们是成年神经元干细胞的调节剂。关键步骤包括将吲哚-2-乙酸甲酯烯醇酯的分子间迈克尔加成至α，β-不饱和N-磺酰内酰胺，以形成生物碱的C15，C16键。该策略的其他特征包括：选择性地部分还原中间N-磺酰内酰胺，然后环化成桥联的缩醛胺系统，这是所有五种生物碱的关键前体，以及使用烯丙基作为掩盖的醛当量。

  DOI：

  10.1021/acs.joc.8b00889
• 作为产物：
  描述：

  3-甲基吲哚 、 溴乙酸甲酯 在 disodium hydrogenphosphate 、 [4,4′-di-tert-butyl-2,2′-bipyridine]bis[5-methyl-2-(4-methyl-2pyridinyl)phenyl]iridium(III) hexafluorophosphate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 20.0h， 以78%的产率得到(3-methyl-1H-indol-2-yl)acetic acid methyl ester
  参考文献：
  名称：

  色胺醇和色胺通过CH官能化的光化学α-羧烷基化。

  摘要：

  已经开发了在可见光照射下通过CH键的官能化使色酚和色胺的α-羧烷基化的方法。该光化学策略在Ir（iii）光催化剂的催化下并与吲哚衍生物偶联，活化了α-溴代烷基羧酸酯的C-Br键以提供以碳为中心的自由基。该方法显示出宽泛的官能团耐受性和优异的区域选择性，并应用于后期功能化和含吲哚杂种的制备。

  DOI：

  10.1039/d0cc00847h

文献信息

• Total Syntheses of the Monoterpenoid Indole Alkaloids (±)-Alstoscholarisine B and C
  作者：Jeremy D. Mason、Steven M. Weinreb

  DOI：10.1002/anie.201710943

  日期：2017.12.22

  Total syntheses of the monoterpenoid indole alkaloids (±)‐alstoscholarisine B and C were accomplished starting from a readily available indole‐2‐acetic ester and an α,β‐unsaturated N‐sulfonyllactam.

  单萜类吲哚生物碱（±）-alstoscholarisine B和C的总合成是从容易获得的吲哚-2-乙酸酯和α，β-不饱和N-磺酰内酰胺开始的。
• Alstoscholarisines H–J, Indole Alkaloids from <i>Alstonia scholaris</i>: Structural Evaluation and Bioinspired Synthesis of Alstoscholarisine H
  作者：Zhiqiang Pan、Xu-Jie Qin、Ya-Ping Liu、Ting Wu、Xiao-Dong Luo、Chengfeng Xia

  DOI：10.1021/acs.orglett.5b03583

  日期：2016.2.19

  Alstoscholarisines H–J (1–3), new monoterpenoid indole alkaloids with an unprecedented skeleton created via the formation of a C-3/N-1 bond, were isolated from Alstonia scholaris. Their structures were established by extensive spectroscopic analyses and the assessment of single-crystal X-ray diffraction data. The total synthesis of alstoscholarisine H was achieved via the regioselective nucleophilic addition

  Alstoscholarisines H-Ĵ（1 - 3），单萜新吲哚生物碱经由C-3 / N-1键的形成创造了前所未有的骨架，从分离灯台树。通过广泛的光谱分析和对单晶X射线衍射数据的评估，确定了它们的结构。alstoscholarisine H的总合成是通过吡啶的区域选择性亲核加成反应实现的，该吡啶鎓是通过生物启发的亚胺离子中间体，然后进行Pictet-Spengler样环化而形成的。
• Enantioselective Intermolecular Formal [3 + 3] Cycloaddition of 2,3-Disubstituted Indoles with Acrolein
  作者：Jianbiao Huang、Long Zhao、Yong Liu、Weiguo Cao、Xiaoyu Wu

  DOI：10.1021/ol401809d

  日期：2013.9.6

  An expedient enantioselective synthesis of highly substituted hydrocarbazoles has been realized by an organocatalyzed formal [3 + 3] cycloaddition between acrolein and 2,3-disubstituted indoles. Tricyclic hydrocarbazoles were obtained from a broad range of 2,3-disubstituted indoles and acrolein in good to excellent yields and excellent enantioselectivites.
• Versatile Synthesis of Quinoline-3-Carboxylic Esters and Indol-2-Acetic Esters by Palladium-Catalyzed Carbonylation of 1-(2-Aminoaryl)-2-Yn-1-Ols
  作者：Bartolo Gabriele、Raffaella Mancuso、Giuseppe Salerno、Elvira Lupinacci、Giuseppe Ruffolo、Mirco Costa

  DOI：10.1021/jo8006495

  日期：2008.7.1

  1-(2-Aminoaryl)-2-yn-1-ols, easily obtained by the Grignard reaction between 1-(2-aminoaryl)ketones and alkynylmagnesium bromides, were subjected to carbonylative conditions in the presence of the PdI2-KI catalytic system, in the presence and in the absence of an external oxidant. Under oxidative conditions (80 arm of a 4:1 mixture of CO-air, in MeOH as the solvent at 100 degrees C and in the presence of 2 mol % of PdI2 and 20 mol % of KI), 1-(2-aminoaryl)-2-yn-1-ols bearing a primary amino group were selectively converted into quinoline-3-carboxylic esters in fair to good yields [45-70%, based on starting 1-(2-aminoaryl)ketones], ensuing from 6-endo-dig cyclization followed by dehydration and oxidative methoxycarbonylation. On the other hand, indol-2-acetic esters, deriving from 5-exo-dig cyclization followed by dehydrating methoxycarbonylation, were selectively obtained in moderate to good yields [42-88%, based on starting 1-(2-aminoaryl)ketones] under nonoxidative conditions (90 arm of CO, in MeOH as the solvent at 100 degrees C and in the presence of 2 mol % of PdI2 and 20 mol % of KI), in the case of 1-(2-aminoaryl)-2-yn-1-ols bearing either a primary or secondary amino group and substituted with a bulky group on the triple bond.
• Photochemical α-carboxyalkylation of tryptophols and tryptamines <i>via</i> C–H functionalization
  作者：Zhiqiang Pan、Yuchang Liu、Fengchi Hu、Qinglong Liu、Wenbin Shang、Chengfeng Xia

  DOI：10.1039/d0cc00847h

  日期：——

  strategy activated the C-Br bonds of α-bromo-alkylcarboxylic esters to provide carbon-centered radicals under the catalysis of Ir(iii) photocatalyst and coupled with indole derivatives. This methodology displayed wide functional group tolerance and excellent regioselectivity, and was applied to the late-stage functionalization and preparation of indole-containing hybrids.

  已经开发了在可见光照射下通过CH键的官能化使色酚和色胺的α-羧烷基化的方法。该光化学策略在Ir（iii）光催化剂的催化下并与吲哚衍生物偶联，活化了α-溴代烷基羧酸酯的C-Br键以提供以碳为中心的自由基。该方法显示出宽泛的官能团耐受性和优异的区域选择性，并应用于后期功能化和含吲哚杂种的制备。