methyl 3-methyl-1H-indole-1-carboxylate | 63703-23-1

• 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: methyl 3-methyl-1H-indole-1-carboxylate
• 英文别名: methyl 3-methyl-1H-indolecarboxylate；1-(methoxycarbonyl)-3-methylindole；3-methyl-indole-1-carboxylic acid methyl ester；methyl 3-methylindole-1-carboxylate
• CAS: 63703-23-1
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: PLYOCHMABYWYHL-UHFFFAOYSA-N

物化性质

• 沸点：
  101-102 °C(Press: 0.5 Torr)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-methyl-1H-indole-1-carboxylate 在 碳酸氢钠 、 oxone 、 edetate disodium 作用下， 以 水 、 丙酮 为溶剂， 反应 2.17h， 以59%的产率得到methyl 3-hydroxy-3-methyl-2-oxoindoline-1-carboxylate
  参考文献：
  名称：

  Microwave-Assisted Synthesis of 3,1-Benzoxazin-2-ones from 3-Hydroxyoxindoles

  摘要：

  A general protocol for the synthesis of 3,1-benzoxazin-2-ones 18 from 3-hydroxyoxindoles 16 in a two steps sequence through phenylsuccinates or phenylpropionates 17 is described. Best reaction conditions for ring opening of 16 to succinates or propionates 17 were achieved using alcohol/silica gel, while cyclization of 17 to benzoxazinones 18 was easily done with HCl/alcohol. It was also found that 17 and 18 can be transesterified using HCl/alcohol. Most transformations were carried out by traditional heating and by microwave (MW) irradiation to accelerate reaction rates.

  DOI：

  10.3987/com-12-12472
• 作为产物：
  描述：

  N-(methoxycarbonyl)-2-(1-methylethenyl)formanilide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 吡啶 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 methyl 3-methyl-1H-indole-1-carboxylate
  参考文献：
  名称：

  顺序的N-酰胺基甲基化-酰胺环封闭复分解：苯并氮杂杂环的构建

  摘要：

  衍生自邻-乙烯基苯胺，邻-烯丙基苯胺和邻-乙烯基苄胺的N-酰基酰胺的二甲基噻吩并茂甲基化反应提供了相应的酰胺，这些酰胺暴露于第二代Grubbs钌催化剂后可生成吲哚，1,4-二氢喹啉和1， 2-二氢异喹啉分别。尽管该闭环复分解（RCM）步骤因烯烃异构化过程而变得复杂，但该顺序方案还允许合成二氢苯并a庚因。从某些基材上，可以在钛介导的步骤中观察到直接环化，这很可能是通过烯烃复分解-分子内烯化序列发生的。

  DOI：

  10.1021/jo061180j

文献信息

• Total Synthesis of Lapidilectine B Enabled by Manganese(III)-Mediated Oxidative Cyclization of Indoles
  作者：Yang Gao、Mengyang Fan、Qixiang Geng、Dawei Ma

  DOI：10.1002/chem.201801312

  日期：2018.5.2

  This unprecedented method enabled the efficient construction of a complex polycyclic scaffold bearing a spiro‐indoline motif and a lactone moiety in one step. Its synthetic utility was demonstrated in the total synthesis of lapidilectine B (in 18 steps) by employing a strategic regioselective ring‐expansion and a silver‐promoted allenic amine cyclization as the additional key elements.

  描述了一种新型的锰（III）介导的容易获得的1,2,3-三取代的吲哚的氧化环化反应。这一前所未有的方法使一步一步就能高效构建带有螺二氢吲哚基序和内酯部分的复杂多环支架。通过策略性的区域选择性环扩环和银促进的烯丙胺环化作为附加的关键元素，可在拉帕迪卡汀B的全合成（18个步骤）中证明其合成用途。
• A catalytic <i>N</i>-deacylative alkylation approach to hexahydropyrrolo[2,3-<i>b</i>]indole alkaloids
  作者：Nivesh Kumar、Arindam Maity、Vipin R. Gavit、Alakesh Bisai

  DOI：10.1039/c8cc04117b

  日期：——

  strategy to diversely functionalized hexahydropyrrolo[2,3-b]indole alkaloids is described in high chemical yields. The synthesis features a key Pd(0)-catalyzed deacylative alkylation of N-acyl 3-substituted indoles using only 1 mol% of Pd(PPh3)4. The scope of this methodology is further defined in the asymmetric synthesis of pyrroloindolines using a diastereoselective approach.

  以高化学产率描述了多样化功能化的六氢吡咯并[2,3- b ]吲哚生物碱的一种通用的前所未有的策略。合成的特征是仅使用1 mol％的Pd（PPh 3）4的N-酰基3取代的吲哚的关键Pd（0）催化的脱酰基烷基化反应。该方法的范围在使用非对映选择性方法不对称合成吡咯并二氢吲哚中进一步定义。
• Aromatic Enamide/Ene Metathesis toward Substituted Indoles and Its Application to the Synthesis of Indomethacins
  作者：Yayoi Kasaya、Kosuke Hoshi、Yukiyoshi Terada、Atsushi Nishida、Satoshi Shuto、Mitsuhiro Arisawa

  DOI：10.1002/ejoc.200900520

  日期：2009.9

  A steric and electronic effect on enamide/ene metathesis, a novel preparation of 2-substituted indoles and 3-substituted indoles using enamide-ene metathesis as a key reaction, and its application to the synthesis of indomethacin are described. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  描述了烯酰胺/烯复分解的空间和电子效应，使用烯酰胺 - 烯复分解作为关键反应制备 2-取代吲哚和 3-取代吲哚的新方法，及其在吲哚美辛合成中的应用。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Gold(I)-Catalyzed Tandem Cyclization Approach to Tetracyclic Indolines
  作者：Yongxiang Liu、Wenqing Xu、Xiang Wang

  DOI：10.1021/ol100153h

  日期：2010.4.2

  Two highly stereoselective cationic gold(I)-catalyzed tandem cyclization reactions of alkynylindoles are described. These reactions demonstrated a novel and general strategy to rapidly construct highly functionalized polycyclic indolines. This approach was successfully employed for a formal synthesis of the akuammiline alkaloid minfiensine.

  描述了炔基吲哚的两个高度立体选择性的阳离子金（I）催化串联环化反应。这些反应证明了快速构建高度官能化的多环吲哚啉的新颖且通用的策略。此方法已成功用于akuammiline生物碱米非斯汀的正式合成。
• Ru-NHC-Catalyzed Asymmetric, Complete Hydrogenation of Indoles and Benzofurans: One Catalyst with Dual Function
  作者：Fuhao Zhang、Himadri Sekhar Sasmal、Constantin G. Daniliuc、Frank Glorius

  DOI：10.1021/jacs.3c04983

  日期：2023.7.26

  The highly enantioselective and complete hydrogenation of protected indoles and benzofurans has been developed, affording facile access to a range of chiral three-dimensional octahydroindoles and octahydrobenzofurans, which are prevalent in many bioactive molecules and organocatalysts. Remarkably, we are in control of the nature of the ruthenium N-heterocyclic carbene complex and employed the complex

  受保护的吲哚和苯并呋喃的高度对映选择性和完全氢化已经被开发出来，可以方便地获得一系列手性三维八氢吲哚和八氢苯并呋喃，它们在许多生物活性分子和有机催化剂中普遍存在。值得注意的是，我们控制了钌N-杂环卡宾配合物的性质，并将该配合物用作均相和非均相催化剂，为其在更具挑战性的芳香族化合物的不对称氢化中的潜在应用提供了新途径。