(4-chloro-2-methyl-phenyl)-carbamic acid tert-butyl ester | 129822-41-9

• 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: (4-chloro-2-methyl-phenyl)-carbamic acid tert-butyl ester
• 英文别名: N-(tert-butoxycarbonyl)-2-amino-5-chlorotoluene；2-methyl-4-chloro-N-tert-butoxycarbonylaniline；N-tert-butoxycarbonyl-4-chloro-2-methylaniline；tert-butyl (4-chloro-2-methylphenyl)carbamate；tert-butyl N-(4-chloro-2-methylphenyl)carbamate
• CAS: 129822-41-9
• 化学式: C₁₂H₁₆ClNO₂
• 分子量: 241.718
• InChiKey: XJCFXYCGQPYEJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-chloro-2-methyl-phenyl)-carbamic acid tert-butyl ester 在 仲丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-chloro-2-propyl-1H-indole
  参考文献：
  名称：

  2-Alkyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles as novel 5-HT6 receptor agonists

  摘要：

  A series of 2-alkyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles were synthesized and evaluated for their 5-HT6 activity. The most potent agonist in this series was 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole with an IC50 = 7.4 nM in H-3-LSD binding and an EC50 = 1.0 nM in a functional assay measuring production of cyclic AMP. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.067
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 4-氯-2-甲基苯胺 以 四氢呋喃 为溶剂， 生成 (4-chloro-2-methyl-phenyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Preparation of Indoles and Oxindoles fromN-(tert-Butoxycarbonyl)-2-alkylanilines

  摘要：

  使用双锂化的N-(叔丁氧羰基)苯胺1与二甲基甲酰胺或二氧化碳反应，可得到中间体3和5，它们分别容易转化为N-(叔丁氧羰基)吲哚4和氧化吲哚（吲哚-2(3H)-酮，7）。双锂化的1与N-甲氧基-N-甲基酰胺缩合得到酮9，这些酮在三氟乙酸处理下环化，根据反应时间的不同，形成2-取代的1-(叔丁氧羰基)吲哚10或2-取代的吲哚11。这一通用方法已被应用于高效合成1,2-烷基桥联吲哚12、1,3,4,5-四氢苯[c,d]吲哚（16）、2a,3,4,5-四氢苯[c,d]吲哚-2(1H)-酮（18）以及1-(叔丁氧羰基)-1H-吡咯并[2,3-b]吡啶（21）。

  DOI：

  10.1055/s-1991-26597

文献信息

• INDOLE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF
  申请人：Tatani Kazuya

  公开号：US20120129890A1

  公开（公告）日：2012-05-24

  A compound (I) of the present invention, which has an EP 1 receptor antagonism: [wherein A represents a benzene ring or the like; Y 1 represents a C 1-6 alkylene group; Y 2 represents a single bond or the like; R 1 represents a hydrogen atom, a C 1-6 alkyl group or the like; R 2 represents a phenyl group which may have a substituent, a 5-membered aromatic heterocyclic ring which may have a substituent, a 6-membered aromatic heterocyclic ring which may have a substituent or the like; R 3 represents a halogen atom, a C 1-6 alkoxy group or the like; R 4 represents a hydrogen atom or the like; and R 5 represents a hydrogen atom or the like] or a pharmaceutically acceptable salt thereof is provided. Furthermore, the compound (I) of the present invention can be used as an agent for treating or preventing LUTS, in particular, various symptoms of OABs.

  本发明提供了一种具有EP1受体拮抗作用的化合物（I）[其中A代表苯环或类似结构；Y1代表C1-6烷基亚基；Y2代表单键或类似结构；R1代表氢原子、C1-6烷基团或类似结构；R2代表可能含有取代基的苯基、可能含有取代基的5元芳香杂环、可能含有取代基的6元芳香杂环或类似结构；R3代表卤素原子、C1-6烷氧基团或类似结构；R4代表氢原子或类似结构；R5代表氢原子或类似结构]或其药物可接受的盐。此外，本发明的化合物（I）可用作治疗或预防LUTS的药物，特别是OAB的各种症状。
• Preparation of Indoles and Oxindoles from<i>N</i>-(<i>tert</i>-Butoxycarbonyl)-2-alkylanilines
  作者：Robin D. Clark、Joseph M. Muchowski、Lawrence E. Fisher、Lee A. Flippin、David B. Repke、Michel Souchet

  DOI：10.1055/s-1991-26597

  日期：——

  Treatment of dilithiated N-(tert-butoxycarbonyl)anilines 1 with dimethylformamide or carbon dioxide furnishes intermediates 3, 5, that are easily converted to N-(tert-butoxycarbonyl)indoles 4 and oxindoles (indol-2(3H)-ones, 7), respectively. Condensation of dilithiated 1 with N-methoxy-N-methylamides provides ketones 9 which are cyclized upon trifluoroacetic acid treatment to either 2-substituted 1-(tert-butoxycarbonyl)indoles 10 or 2-substituted indoles 11 depending on the reaction time. This general methodology has been applied to efficient synthesis of 1,2-alkyl-bridged indoles 12, 1,3,4,5-tetrahydrobenz[c,d]indole (16), 2a,3,4,5-tetrahydrobenz [c,d]indol-2(1H)-one (18), and 1-(tert-butoxycarbonyl) -1H-pyrrolo[2,3-b]pyridine (21).

  使用双锂化的N-(叔丁氧羰基)苯胺1与二甲基甲酰胺或二氧化碳反应，可得到中间体3和5，它们分别容易转化为N-(叔丁氧羰基)吲哚4和氧化吲哚（吲哚-2(3H)-酮，7）。双锂化的1与N-甲氧基-N-甲基酰胺缩合得到酮9，这些酮在三氟乙酸处理下环化，根据反应时间的不同，形成2-取代的1-(叔丁氧羰基)吲哚10或2-取代的吲哚11。这一通用方法已被应用于高效合成1,2-烷基桥联吲哚12、1,3,4,5-四氢苯[c,d]吲哚（16）、2a,3,4,5-四氢苯[c,d]吲哚-2(1H)-酮（18）以及1-(叔丁氧羰基)-1H-吡咯并[2,3-b]吡啶（21）。
• Substituted indoles as alpha-1 agonists
  申请人：——

  公开号：US20030220319A1

  公开（公告）日：2003-11-27

  This invention relates to compounds which are alpha-1 receptor agonists, preferably alpha-1A/L receptor agonists, and which are represented by Formula I: 1 wherein X is —S(O) n — or —C(O)—, A is C 1-6 alkyl, aryl, heteroaryl, hydroxyalkyl, or —(CH 2 ) p —NR a R b , and the other substituents are as defined in the specification; or individual isomers, racemic or non-racemic mixtures of isomers, or pharmaceutically acceptable salts or solvates thereof. The invention further relates to pharmaceutical compositions containing such compounds, methods for their use as therapeutic agents, and methods of preparation thereof.

  这项发明涉及α-1受体激动剂，优选为α-1A/L受体激动剂，其化学式如下：其中X为—S(O)n—或—C(O)—，A为C1-6烷基，芳基，杂环芳基，羟基烷基，或—(CH2)p—NRaRb，其他取代基如规范中所定义；或其各个异构体，消旋体或非消旋体混合物，或其药用盐或溶剂化合物。该发明还涉及含有这类化合物的药物组合物，以及它们作为治疗剂的使用方法和制备方法。
• Generation of oxindole-2-thiones (thiols) via dilithiated<i>N</i>-<i>tert</i>-Boc-anilines. Synthesis of a sulfur analog of MK886
  作者：Alicia Cervantes、Claudia A. Contreras、Angel Guzman、Elena E. Vale、Esperanza Velarde、Sylvie L. Berthiaume、Joseph M. Muchowski

  DOI：10.1139/v95-045

  日期：1995.3.1

  N-tert-butoxycarbonyl-2-alkoxycarbonylmethylanilines 11a, b were converted into the N-tert-butoxycarbonyl-oxindole-2-thiones(thiols) 7a–c and 14a, b, respectively, by sequential reaction with carbon disulfide and methyl iodide. Compound 7b was converted into 10d, the sulfur analog of MK886. Keywords: N-tert-butoxycarbonyl-2-alkylthiomethylanilines, dilithiation, N-tert-butoxycarbonyl-2-alkoxycarbonylmethylanilines

  N-叔丁氧羰基-2-烷硫基甲基苯胺 5a-c 和 N-叔丁氧羰基-2-烷氧羰基甲基苯胺 11a、b 的 N,C-二锂化衍生物被转化为 N-叔丁氧羰基-羟吲哚-2-硫酮(硫醇) 7a-c 和 14a, b，分别通过与二硫化碳和甲基碘的顺序反应。化合物 7b 被转化为 10d，即 MK886 的硫类似物。关键词：N-叔丁氧羰基-2-烷硫基甲基苯胺，二锂化，N-叔丁氧羰基-2-烷氧羰基甲基苯胺，N-叔丁氧羰基羟吲哚-2-硫酮。
• Oxidative Cyclization of Amino Alcohols Catalyzed by a Cp*Ir Complex. Synthesis of Indoles, 1,2,3,4-Tetrahydroquinolines, and 2,3,4,5-Tetrahydro-1-benzazepine
  作者：Ken-ichi Fujita、Kazunari Yamamoto、Ryohei Yamaguchi

  DOI：10.1021/ol026200s

  日期：2002.8.1

  oxidative cyclization of amino alcohols has been revealed. Indole derivatives are synthesized in good to excellent yields from 2-aminophenethyl alcohols by means of a [CpIrCl(2)](2)/K(2)CO(3) catalytic system. The present catalytic system is also effective for syntheses of 1,2,3,4-tetrahydroquinolines from 3-(2-aminophenyl)propanols and 2,3,4,5-tetrahydro-1-benzazepine from 4-(2-aminophenyl)butanol.

  [反应：见正文]已经揭示了一种新的铱催化的氨基醇氧化环化反应。吲哚衍生物是通过[CpIrCl（2）]（2）/ K（2）CO（3）催化系统从2-氨基苯乙醇以极高的产率合成的。本催化体系对于由3-（2-氨基苯基）丙醇合成1,2,3,4-四氢喹啉和由4-（2-氨基苯基）合成2,3,4,5-四氢-1-苯并ze庚因也是有效的。丁醇。