N-<2-(toluenesulfonyl)oxyethyl>indole | 148806-53-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-<2-(toluenesulfonyl)oxyethyl>indole
• 英文别名: 1H-Indole-1-ethanol, 1-(4-methylbenzenesulfonate)；2-indol-1-ylethyl 4-methylbenzenesulfonate
• CAS: 148806-53-5
• 化学式: C₁₇H₁₇NO₃S
• 分子量: 315.393
• InChiKey: UFJCFODRSPRPBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  56.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-<2-(toluenesulfonyl)oxyethyl>indole 在 正丁基锂 、 sodium iodide 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 15.0h， 生成 3-((2-indol-1-yl)ethyl)piperidin-2-one
  参考文献：
  名称：

  Intramolecular Cycloaddition of Isomunchnone Dipoles to Heteroaromatic .pi.-Systems

  摘要：

  A series of furanyl-, thienyl-, and indole-substituted diazo imides were prepared by treating the appropriate amides with diketene to give the N-acetoacylated imides. Exposure of the imides to standard diazo transfer conditions afforded the desired diazo imides. Treatment of these diazo imides bearing tethered heterocyclic rings with rhodium(II) acetate affords transient isomunchnone dipoles. The mesoionic dipoles are formed by cyclization of the rhodium carbenoid onto the neighboring amide carbonyl oxygen atom. The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of the isomunchnones across a tethered furan and thiophene ring were studied. The facility of the internal cycloaddition is influenced by the length and nature of the tether connecting the dipole and dipolarophile functionalities. The reaction is critically dependent on conformational factors in the transition state. In addition, the first examples of intramolecular cycloaddition of isomunchnones to indole dipolarophiles are reported. Cycloadditions of this type generate highly functionalized polyheterocyclic systems with complete relative stereocontrol at the newly formed stereocenters.

  DOI：

  10.1021/jo00102a037
• 作为产物：
  描述：

  1-<2-(Tetrahydropyran-2-yloxy)ethyl>-1H-indole 在 吡啶 、 对甲苯磺酸 作用下， 以 甲醇 、 水 为溶剂， 反应 26.0h， 生成 N-<2-(toluenesulfonyl)oxyethyl>indole
  参考文献：
  名称：

  8H-Anhydro-4-hydroxy-2-oxo-1,3-thiazinium Hydroxides as Mesoionic 1,4-Dipoles

  摘要：

  The previously unknown 8H-anhydro-4-hydroxy-2-oxo-1,3-thiazinium hydroxides (1) were prepared and their 1,4-dipolar cycloaddition behavior was examined. In most cases, elimination of the proton in the 8-position of the mesoionic ring was observed to occur unless extremely reactive dipolarophiles were used. The S,N-ketene acetals were converted to the corresponding alpha-diazo ketones for further study.

  DOI：

  10.3987/com-93-s(b)16-1

文献信息

• Enantioselective Fujiwara-Moritani Indole and Pyrrole Annulations Catalyzed by Chiral Palladium(II)-NicOx Complexes
  作者：Julia A. Schiffner、Thorsten H. Wöste、Martin Oestreich

  DOI：10.1002/ejoc.200901129

  日期：2010.1

  catalytic asymmetric Fujiwara-Moritani ring closures of several indole- and pyrrole-based cyclization precursors are reported. These unprecedented oxidative palladium(II)-catalyzed annulations allow for the formation of a stereogenic quaternary carbon atom, and decent levels of enantiocontrol are seen in 5-exo-trig cyclizations (54 % ee for an indole and 76 % ee for a pyrrole) while 6-exo-trig ring

  报道了几种基于吲哚和吡咯的环化前体的催化不对称 Fujiwara-Moritani 闭环。这些前所未有的氧化钯 (II) 催化环化允许形成立体季碳原子，并且在 5-exo-trig 环化（吲哚 54 % ee 和吡咯 76 % ee）中看到了相当水平的对映控制而 6-exo-trig 闭环提供了基本上外消旋的材料。具有尼古丁平台 (NicOx) 的新型恶唑啉配体对于良好的催化转化至关重要，因为传统的 PyOx 配体无法产生可接受的化学产率。详细描述了这些 NicOx 配体的制备以及环化前体的合成。
• 基于异恶唑取代苯甲酰胺类衍生物及抗前列腺癌药物应用
  申请人：浙江师范大学

  公开号：CN113861186B

  公开（公告）日：2023-08-25

  本发明公开了一类式(I)、式(II)结构的基于异恶唑取代苯甲酰胺类衍生物及抗前列腺癌药物应用，这类异恶唑取代苯甲酰胺类衍生物，可以有效抑制雄激素受体的活性，同时进一步的实验证实，这类化合物可以降解全长雄激素受体以及雄激素受体可变剪接体，是一类新型的雄激素拮抗剂，可以应用于雄激素依赖的抗前列癌药物治疗。
• 3-Arylcarbonyl-1-aminoalkyl-1H-indole containing antiglaucoma compositions
  申请人：STERLING WINTHROP INC.

  公开号：EP0445781A1

  公开（公告）日：1991-09-11

  Antiglaucoma compositions containing 3-arylcarbonyl-1-aminoalkyl-1H-indoles, as the active component thereof, and a method of use thereof in the treatment of glaucoma. Also included are novel 3-arylcarbonyl-1-aminoalkyl-1H-indoles.

  含有作为其活性成分的 3-芳基羰基-1-氨基烷基-1H-吲哚的抗青光眼组合物及其治疗青光眼的使用方法。此外，还包括新型 3-芳基羰基-1-氨基烷基-1H-吲哚。
• Intramolecular Cycloaddition of Isomunchnone Dipoles to Heteroaromatic .pi.-Systems
  作者：Albert Padwa、Donald L. Hertzog、William R. Nadler

  DOI：10.1021/jo00102a037

  日期：1994.11

  A series of furanyl-, thienyl-, and indole-substituted diazo imides were prepared by treating the appropriate amides with diketene to give the N-acetoacylated imides. Exposure of the imides to standard diazo transfer conditions afforded the desired diazo imides. Treatment of these diazo imides bearing tethered heterocyclic rings with rhodium(II) acetate affords transient isomunchnone dipoles. The mesoionic dipoles are formed by cyclization of the rhodium carbenoid onto the neighboring amide carbonyl oxygen atom. The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of the isomunchnones across a tethered furan and thiophene ring were studied. The facility of the internal cycloaddition is influenced by the length and nature of the tether connecting the dipole and dipolarophile functionalities. The reaction is critically dependent on conformational factors in the transition state. In addition, the first examples of intramolecular cycloaddition of isomunchnones to indole dipolarophiles are reported. Cycloadditions of this type generate highly functionalized polyheterocyclic systems with complete relative stereocontrol at the newly formed stereocenters.
• Development of novel telomerase inhibitors based on a Bisindole unit
  作者：Shigeki Sasaki、Takeru Ehara、Ikuhiro Sakata、Yasuhiro Fujino、Naozumi Harada、Junko Kimura、Hideo Nakamura、Minoru Maeda

  DOI：10.1016/s0960-894x(01)00002-6

  日期：2001.2

  Telomerase is the enzyme that elongates telomere repeat at the ends of a chromosome. As high telomerase activity is observed in most cancer cells, inhibitors of human telomerase have been expected as new chemotherapeutic agents for cancer. We describe here the discovery of novel inhibitors with IC50 values in the submicromolar range. The structure of the novel inhibitors will be useful as a scaffold for construction of the library in the search for telomerase inhibitors. (C) 2001 Elsevier Science Ltd. All rights reserved.