ethyl 1-benzylindoline-2-carboxylate | 97608-38-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 1-benzylindoline-2-carboxylate
• 英文别名: 2,3-dihydro-2-ethoxycarbonyl-1-benzyl-1H-indole；Ethyl 1-benzyl-2,3-dihydroindole-2-carboxylate
• CAS: 97608-38-3
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: KUKMYKQCNPGZAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-benzylindoline-2-carboxylate 在 manganese(IV) oxide 作用下， 以 甲苯 为溶剂， 反应 96.0h， 以90%的产率得到1-苄基-1H-吲哚-2-羧酸乙酯
  参考文献：
  名称：

  Synthesis of Indolines by a Zn-Mediated Mannich Reaction/Pd-Catalyzed Amination Sequence

  摘要：

  1,2-Disubstituted indolines have been prepared in fair to good yields by a Zn-mediated organometallic Mannich reaction, followed by an intramolecular Pd-catalyzed aromatic amination. The reactions are easy to set up and compatible with a large variety of simple or commercially available reagents. The method was further extended to the preparation of a 1,2,3-trisubstituted indoline.

  DOI：

  10.1021/acs.joc.7b00013
• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 在 sodium hydride 、 sodium cyanoborohydride 作用下， 以 二甲基亚砜 、 三氟乙酸 为溶剂， 反应 2.0h， 生成 ethyl 1-benzylindoline-2-carboxylate
  参考文献：
  名称：

  Indoline analogs of idazoxan: potent .alpha.2-antagonists and .alpha.1-agonists

  摘要：

  The synthesis and alpha-adrenergic activity of a series of substituted 2-imidazolinylindolines are described. Substitution in the indoline ring generated compounds with a spectrum of adrenoceptor antagonist/agonist profiles that proved sensitive to both the nature and position of the substituent. Many of the derivatives possess greater presynaptic antagonist potency than the corresponding benzodioxan 1, dihydrobenzofuran 2, and indan 3 analogues; however, this alpha 2-antagonism is often accompanied by alpha 1-agonist activity. It was not possible to separate alpha 2-antagonist from alpha 1-agonist properties in this series. Compounds of most interest proved to be the N-ethyl 6, 5-chloro-N-methyl 18, and 5-chloro-N-ethyl 23 derivatives, all being potent alpha 2-antagonists and alpha 1-agonists. Substitution at the 4- and 7-position of the indoline ring generally gave compounds with nonselective agonist properties.

  DOI：

  10.1021/jm00400a009

文献信息

• Access to C5-Alkylated Indolines/Indoles via Michael-Type Friedel–Crafts Alkylation Using Aryl-Nitroolefins
  作者：Berrak Ertugrul、Haydar Kilic、Farrokh Lafzi、Nurullah Saracoglu

  DOI：10.1021/acs.joc.8b00973

  日期：2018.8.17

  C5-alkylated indolines/indoles has been developed. The strategy is composed of Zn(OTf)2-catalyzed Friedel–Crafts alkylation of N-benzylindolines with nitroolefins, and a series of diverse indolines was first obtained in up to 99% yield. This reaction provides a direct and practical route to a variety of the C5-alkylated indolines which were also utilized for accessing corresponding indoles. Indoline derivatives

  已经开发出一种直接合成C5-烷基化的吲哚/吲哚的合成路线。该策略由Zn（OTf）2催化的N-苄基二氢吲哚与硝基烯烃的Friedel-Crafts烷基化反应组成，首先获得了多种多样的二氢吲哚，收率高达99％。该反应提供了直接和实用的途径，以得到各种C5-烷基化的二氢吲哚，它们也被用于获得相应的吲哚。具有游离NH基的二氢吲哚衍生物可通过N-脱保护反应获得。而且，二氢吲哚和吲哚中的伯烷基硝基都适合于进一步的合成精制，从而扩大了产物的多样性。
• .alpha..sub.2 antagonistic
  申请人：——

  公开号：US04598086A1

  公开（公告）日：1986-07-01

  Indole derivatives, in the form of racemates or optically active isomers, of the formula (I) ##STR1## in which R.sub.1 is a hydrogen atom, a linear or branched (C.sub.1-6) alkyl group, a (C.sub.3-6) cycloalkyl-(C.sub.1-4) alkyl group, a (C.sub.2-6) alkenyl group, the naphthylmethyl group, the phenethyl group or a benzyl group optionally substituted by one or more halogen atom or methyl, methoxyl or methylenedioxy group and R.sub.2 is H or a (C.sub.1-4) alkyl or allyl group, and their pharmaceutically acceptable salts; are .alpha..sub.2 -antagonists and useful for the treatment of depression, hypotension, post-operative paralytic ileum, asthma and obesity.

  吲哚衍生物，以盘旋体或旋光异构体的形式存在，其化学式为（I）其中R.sub.1是氢原子，线性或支链（C.sub.1-6）烷基基团，（C.sub.3-6）环烷基-(C.sub.1-4)烷基基团，（C.sub.2-6）烯基基团，萘甲基基团，苯乙基基团或苄基基团，可选择地被一个或多个卤素原子或甲基、甲氧基或亚甲二氧基基团取代，且R.sub.2为H或（C.sub.1-4）烷基或烯丙基基团，以及它们的药学上可接受的盐；是α2-拮抗剂，可用于治疗抑郁症、低血压、术后麻痹性肠梗阻、哮喘和肥胖症。
• C−H Bond Activation Relay (CHAR) of Proline Ester Derivatives Promoted by In Situ Triarylamine Radical Cation: Selective Synthesis of 4‐Bromopyrrole Derivatives
  作者：Han Ding、Shuwei Zhang、Zheng Sun、Qiyuan Ma、Yuemei Li、Yu Yuan、Xiaodong Jia

  DOI：10.1002/chem.202203654

  日期：——

  A C−H activation relay (CHAR) of proline esters was realized by the in situ generated tris(4-bromophenyl)amine radical cation, selectively constructing the skeleton of 4-bromopyrrole under mild reaction conditions.

  通过原位生成的三（4-溴苯基）胺基阳离子，在温和的反应条件下选择性地构建 4-溴吡咯的骨架，实现了脯氨酸酯的 AC-H 活化中继（CHAR）。
• .alpha.2-Adrenergic agonists/antagonists: the synthesis and structure-activity relationships of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines
  作者：Dennis J. Hlasta、Daniel Luttinger、Mark H. Perrone、Marla J. Silbernagel、Susan J. Ward、Dean R. Haubrich

  DOI：10.1021/jm00392a005

  日期：1987.9

  The synthesis and alpha 2-adrenergic activity of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines are described. The indolin-2-yl imidazoline 4b was found to possess potent alpha 2-adrenergic agonist and antagonist activity. The modification of the substituents on the indoline ring of 4b has led to the separation of these activities. Substitution on the aromatic ring of 4b with halogen or increasing the size of the N-alkyl substituent of 4b gave alpha 2-adrenergic antagonists without agonist activity. The N-allylindoline 4d is more potent than idazoxan in vitro and is equipotent in vivo, but is less receptor selective (alpha 2 vs. alpha 1) than idazoxan. The cis-1,3-dimethylindolin-2-yl imidazoline 6a is an alpha 2-adrenergic agonist equal in potency to clonidine in vitro, while the trans-1,3-dimethylindolin-2-yl imidazoline 6b is a moderately potent alpha 2-adrenergic antagonist.
• HLASTA, DENNIS J.;LUTTINGER, DANIEL;PERRONE, MARK H.;SILBERNAGEL, MARLA J+, J. MED. CHEM., 30,(1987) N 9, 1555-1562
  作者：HLASTA, DENNIS J.、LUTTINGER, DANIEL、PERRONE, MARK H.、SILBERNAGEL, MARLA J+

  DOI：——

  日期：——