Ethyl 6-[(2,2,4,4-tetramethylchroman-6-yl)-ethynyl]nicotinate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: Ethyl 6-[(2,2,4,4-tetramethylchroman-6-yl)-ethynyl]nicotinate
• 英文别名: ethyl 6-[2-(2,2,4,4-tetramethyl-3H-chromen-6-yl)ethynyl]pyridine-3-carboxylate
• 化学式: C₂₃H₂₅NO₃
• 分子量: 363.4
• InChiKey: ZLGPKNIPUWZRSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,2,4,4-tetramethyl-6-ethynyl-chroman 、 6-氯烟酸乙酯 、 在 双三苯基磷二氯化钯 氩 、 三乙胺 、 silica 、 乙酸乙酯 、 hexanes 作用下， 以 三乙胺 为溶剂， 反应 80.0h， 生成 Ethyl 6-[(2,2,4,4-tetramethylchroman-6-yl)-ethynyl]nicotinate
  参考文献：
  名称：

  Acetylenes disubstituted with a heteroaromatic group and a 2-substituted

  摘要：

  化合物的公式为 ##STR1## 其中 X 为 S、O 或 NR'；R' 为氢或低碳基；R.sub.1、R.sub.2 和 R.sub.3 为氢或低碳基；R.sub.4 和 R.sub.5 为氢或低碳基，但 R.sub.4 和 R.sub.5 不能同时为氢；A 为吡啶基、噻吩基、呋喃基、吡嗪基、嘧啶基、吡唑基、噻唑基或氧唑基；n 为 0-5，B 为 H、--COOH 或其药学上可接受的盐、酯或酰胺、--CH.sub.2 OH 或其醚或酯衍生物、--CHO 或其缩醛衍生物、或--COR.sub.1 或其缩醛衍生物，其中 R.sub.1 为 --(CH.sub.2).sub.m CH.sub.3，m 为 0-4，或其药学上可接受的盐。

  公开号：

  US05272156A1

文献信息

• Acetylenes disubstituted with a thienyl or furyl group and a
  申请人：Allergan

  公开号：US05599819A1

  公开（公告）日：1997-02-04

  Retinoid-like activity is exhibited by compounds of the formula ##STR1## where X is NR'; where R' is hydrogen or lower alkyl; R.sub.1, R.sub.2 and R.sub.3 are hydrogen or lower alkyl; R.sub.4 and R.sub.5 are hydrogen or lower alkyl with the proviso that R.sub.4 and R.sub.5 cannot both be hydrogen, A is thienyl, furyl; n is 0-5, and B is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR.sub.1 or a ketal derivative where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4, or a pharmaceutically acceptable salt thereof.

  化合物的公式为##STR1##，其中X为NR'，R'为氢或低碳基；R.sub.1、R.sub.2和R.sub.3为氢或低碳基；R.sub.4和R.sub.5为氢或低碳基，但是R.sub.4和R.sub.5不能同时为氢；A为噻吩基、呋喃基；n为0-5，B为H、--COOH或其药学上可接受的盐、酯或酰胺、--CH.sub.2 OH或其醚或酯衍生物、--CHO或其缩醛衍生物、或--COR.sub.1或其缩酮衍生物，其中R.sub.1为--(CH.sub.2).sub.m CH.sub.3，m为0-4，或其药学上可接受的盐。
• Process and intermediates for preparing compounds having a disubstituted
  申请人：Allergan, Inc.

  公开号：US05248777A1

  公开（公告）日：1993-09-28

  A process is disclosed for the preparation of disubstituted acetylene derivatives having retinoic acid like biological activity, wherein 6-ethynyl-chroman, 6-ethynyl-thio chroman and 6-ethynyl-1,2,3,4-tetrahydroquinoline derivatives of the formula shown below are reacted in the presence of catalysts with halogenated phenyl or heteroaryl derivatives of the formula shown below to provide the disubstituted acetylenes. In the formulae the symbols have the following meanings. R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen or lower alkyl groups (of 1-6 carbons) where R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 may be identical or different from one another) X is S, O or NR' where R' is hydrogen or lower alkyl, Z represents hydrogen, or a metal ion capable of forming a salt with the ethynyl moiety of the molecule, X' is a leaving group such as a halogen group, A is phenyl, or heteroaryl such as pyridinyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl or oxazolyl, n is an integer between 0 to 5, and B is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR.sub.1 or a ketal derivative where R.sub.1 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons. ##STR1##

  本发明公开了一种制备具有类视黄酸生物活性的二取代乙炔衍生物的过程，其中在催化剂的存在下，通过以下式子所示的6-乙炔基香豆素、6-乙炔基硫代香豆素和6-乙炔基-1,2,3,4-四氢喹啉衍生物与以下式子所示的卤代苯基或杂环基衍生物反应，以提供二取代乙炔衍生物。在式子中，符号具有以下含义。R.sub.1、R.sub.2、R.sub.3、R.sub.4和R.sub.5为氢或较低的烷基（1-6碳）基团，其中R.sub.1、R.sub.2、R.sub.3、R.sub.4和R.sub.5可以相同或不同）X为S、O或NR'，其中R'为氢或较低的烷基，Z表示氢或能够与分子的乙炔基团形成盐的金属离子，X'是卤素基团等离子体，A是苯基或杂环基，例如吡啶基、噻吩基、呋喃基、吡嗪基、嘧啶基、吡嗪啉基、噻唑基或噁唑基，n是0到5之间的整数，B是H、--COOH或其药学上可接受的盐、酯或酰胺，--CH.sub.2 OH或其醚或酯衍生物，或--CHO或其缩醛衍生物，或--COR.sub.1或其缩酮衍生物，其中R.sub.1是含有1到5个碳的烷基、环烷基或烯基基团。
• Compounds having a disubstituted acetylene moiety and retinoic acid-like
  申请人：Allergan, Inc.

  公开号：US05023341A1

  公开（公告）日：1991-06-11

  Disubstituted acetylene thiochroman containing derivatives of the formulae below wherein the symbols have the following meanings; R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen or lower alkyl groups (of 1-6 carbons) where R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 may be identical or different from one another) X is S ##STR1##

  含有以下式子的二取代乙炔硫色烷衍生物，其中符号具有以下含义：R.sub.1，R.sub.2，R.sub.3，R.sub.4和R.sub.5是氢或较低的烷基（1-6个碳），其中R.sub.1，R.sub.2，R.sub.3，R.sub.4和R.sub.5可以相同也可以不同）X为S ## STR1 ##
• Ethynyl-chroman compounds
  申请人：Allergan, Inc.

  公开号：US05053523A1

  公开（公告）日：1991-10-01

  6-Ethynyl-chroman derivatives wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5, hydrogen or lower alkyl groups of one to six carbons wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may be identical or different from one another, X is oxygen, and Z is hydrogen of the following formula: ##STR1##

  6-乙炔基香豆素衍生物，其中R.sub.1、R.sub.2、R.sub.3、R.sub.4和R.sub.5是氢或碳数为1至6的低级烷基，其中R.sub.1、R.sub.2、R.sub.3、R.sub.4和R.sub.5可以相同或不同，X为氧，Z为以下公式中的氢：##STR1##
• Acetylenes disubstituted with a heteroaromatic group and A 2-substituted chromanyl, thiochromanyl or 1,2,3,4- tetrahydroquinolinyl group having retinoid-like activity
  申请人：ALLERGAN, INC.

  公开号：EP0419130A2

  公开（公告）日：1991-03-27

  Retinoid-like activity is exhibited by compounds of the formula where X is S, O or NR′; where R′ is hydrogen or lower alkyl; R₁, R₂ and R₃ are hydrogen or lower alkyl; R₄ and R₅ are hydrogen or lower alkyl with the proviso that R₄ and R₅ cannot both be hydrogen, A is pyridyl, thienyl, furyl, pyridazinyl, pirimidinyl, pyrazinyl, thiazolyl or oxazolyl; n is 0 - 5, and B is H, -COOH or a pharmaceutically acceptable salt, ester or amide thereof, -CH₂OH or an ether or ester derivative, or -CHO or an acetal derivative, or -COR₁ or a ketal derivative where R₁ is -(CH₂)mCH₃ where m is 0-4, or a pharmaceutically accept­able salt thereof.

  式中的化合物具有类视黄醇活性 其中 X 是 S、O 或 NR′； 其中 R′是氢或低级烷基； R₁、R₂ 和 R₃ 是氢或低级烷基；R₄ 和 R₅ 是氢或低级烷基，但 R₄ 和 R₅ 不能都是氢， A 是吡啶基、噻吩基、呋喃基、哒嗪基、吡啶基、吡嗪基、噻唑基或噁唑基；n 是 0 - 5，且 B 是 H、-COOH 或其药学上可接受的盐、酯或酰胺、-CH₂OH 或醚或酯衍生物、或 -CHO 或缩醛衍生物、或 -COR₁ 或缩酮衍生物（其中 R₁ 是 -(CH₂)mCH₃ ，其中 m 是 0-4）或其药学上可接受的盐。