3-(2-溴乙基)香豆素 | 20972-54-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 3-(2-溴乙基)香豆素
• 英文名称: 3-(2-bromoethyl)-2H-1-benzopyran-2-one
• 英文别名: 3-(2-Bromoethyl)coumarin；3-(2-bromoethyl)chromen-2-one
• CAS: 20972-54-7
• 化学式: C₁₁H₉BrO₂
• 分子量: 253.095
• InChiKey: KWYQUOMBGREDBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-溴乙基)香豆素 、 丁烯酮 在 2,6-二叔丁基-4-甲基苯酚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以76%的产率得到10-acetyl-7,8,9,10-tetrahydrodibenzo-α-pyrone
  参考文献：
  名称：

  3-Vinylcoumarins and 3-vinylchromenes as dienes. Application to the synthesis of 3,4-fused coumarins and chromenes

  摘要：

  The reaction of alpha-(diethylphosphono)-gamma-butyrolactones 1 with o-hydroxyaryl aldehydes 2 and 7 gave 3-(2-hydroxyethyl)coumarins 3 in excellent yields. Treatment of 3 or 3-(2-hydroxyethyl)-2,2-dimethylchromenes 11 derived from 3 with triphenylphosphine dibromide led to the corresponding 3-(2-bromoethyl)coumarins 8 or 3-(2-bromoethyl)chromenes 12 in good yields. The Diels-Alder reaction of the 3-vinylcoumarins 13 or the 3-vinylchromenes 31, generated in situ from treatment of the bromides 8 or 12 with DBU, with a variety of dienophiles 14-19 and 35 produced regiospecific [2 + 4] cycloadducts, 3,4-fused coumarins 20-28 or 3,4-fused chromenes 32-34 and 36 in good to moderate yields.

  DOI：

  10.1021/jo00027a032
• 作为产物：
  描述：

  3-(2-hydroxyethyl)-2H-chromen-2-one 在 triphenylphosphine dibromide 1:1 addition complex 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以98%的产率得到3-(2-溴乙基)香豆素
  参考文献：
  名称：

  3-Vinylcoumarins and 3-vinylchromenes as dienes. Application to the synthesis of 3,4-fused coumarins and chromenes

  摘要：

  The reaction of alpha-(diethylphosphono)-gamma-butyrolactones 1 with o-hydroxyaryl aldehydes 2 and 7 gave 3-(2-hydroxyethyl)coumarins 3 in excellent yields. Treatment of 3 or 3-(2-hydroxyethyl)-2,2-dimethylchromenes 11 derived from 3 with triphenylphosphine dibromide led to the corresponding 3-(2-bromoethyl)coumarins 8 or 3-(2-bromoethyl)chromenes 12 in good yields. The Diels-Alder reaction of the 3-vinylcoumarins 13 or the 3-vinylchromenes 31, generated in situ from treatment of the bromides 8 or 12 with DBU, with a variety of dienophiles 14-19 and 35 produced regiospecific [2 + 4] cycloadducts, 3,4-fused coumarins 20-28 or 3,4-fused chromenes 32-34 and 36 in good to moderate yields.

  DOI：

  10.1021/jo00027a032

文献信息

• ((Pharmacologically active bicyclic heterocyclic)methyl and -heteroatom)
  申请人：Janssen Pharmaceutica N.V.

  公开号：US04988689A1

  公开（公告）日：1991-01-29

  [(Bicyclic heterocyclyl)methyl and -hetero] substituted hexahydro-1H-azepines and pyrrolidines and their pharmaceutically acceptable acid addition salts having anti-histaminic properties, compositions containing the same, and methods of treating allergic diseases in warm-blooded animals.

  含有抗组胺特性的[(双环杂环基)甲基和-杂原子]取代的六氢-1H-氮杂环庚烷和吡咯烷及其药用可接受的酸盐，包含这些化合物的组合物，以及治疗温血动物过敏疾病的方法。
• Pharmacologically active (Bicyclic heterocyclyl)methyl and -hetero)
  申请人：Janssen Pharmaceutica N.V.

  公开号：US05151424A1

  公开（公告）日：1992-09-29

  [(Bicyclic heterocyclyl)methyl and -hetero] substituted hexahydro-1H-azepines and pyrrolidines and their pharmaceutically acceptable acid addition salts having anti-histaminic properties, compositions containing the same, and methods of treating allergic diseases in warm-blooded animals.

  含有[(双环杂环基)甲基和-杂原子]取代的六氢-1H-氮杂烷和吡咯烷及其药学上可接受的酸盐，具有抗组胺药性，含有这些化合物的组合物以及在温血动物中治疗过敏疾病的方法。
• Anti-hystaminic [(bicyclic heterocyclyl) methyl and --hetero]
  申请人：Janssen Pharmaceutica N.V.

  公开号：US05071846A1

  公开（公告）日：1991-12-10

  [(Bicyclic heterocyclyl)methyl and --hetero] substituted hexahydro--1H--azepines and pyrrolidines and their pharmaceutically acceptable acid addition salts having anti--histaminic properties, compositions containing the same, and methods of treating allergic diseases in warm-blooded animals.

  含有[(双环杂环基)甲基和-杂环] 取代的六氢-1H-氮杂环和吡咯烷及其药学上可接受的酸盐，具有抗组胺特性，含有相同成分的组合物，以及治疗温血动物过敏疾病的方法。
• N-(4-piperidinyl) bicyclic condensed 2-imidazolamine derivatives
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0151824A2

  公开（公告）日：1985-08-21

  Novel N-heterocyclyl-4-piperidinamines of formula wherein L is a radical of formula Het-Alk- (b-5); (lower alkenyl)-Y1-Alk- (b-6); or Ar1-Alk-(b-7); the pharmaceutically acceptable acid addition salts and possible stereochemically isomeric forms thereof, which compounds are anti-allergic agents, pharmaceutical compositions containing such compounds as an active ingredient and processes for preparing the said compounds and compositions.

  式中的新型 N-杂环基-4-哌啶胺 其中 L 是式中的一个基团 Het-Alk-(b-5)；(低级烯基)-Y1-Alk-(b-6)；或 Ar1-Alk-(b-7)；药学上可接受的酸加成盐及其可能的立体化学异构形式，这些化合物是抗过敏剂，含有此类化合物作为活性成分的药物组合物，以及制备上述化合物和组合物的工艺。
• [(Bicyclic heterocyclyl)methyl and -hetero] substituted hexahydro-1H-azepines and pyrrolidines
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0297661A1

  公开（公告）日：1989-01-04

  Novel [(Bicyclic heterocyclyl)methyl and -hetero] substituted hexahydro-­1H-azepines and pyrrolidines of formula wherein     -A¹=A²-A³=A⁴- is -CH=CH-CH=CH-, -N=CH-CH=CH-, -CH=N-CH=CH-, -CH=CH-N=CH-, -CH=CH-CH=N-, -N=CH-N=CH-, or -CH=N-CH=N-,     R¹ is hydrogen, C₁₋₁₀alkyl, C₃₋₆cycloalkyl, Ar¹ or C₁₋₆alkyl substituted with one or two Ar¹ radicals;     B is NR², CH₂, O, S, SO or SO₂;     R is hydrogen or C₁₋₆alkyl;     n is 0 or 2;     L is hydrogen, C₁₋₆alkylcarbonyl, C₁₋₆alkylsulfonyl, C₁₋₆alkyloxy­carbonyl, Ar²-C₁₋₆alkyloxycarbonyl, Ar²-carbonyl, Ar²-sulfonyl, C₃₋₆cycloalkyl, C₂₋₆alkenyl optionally substituted with Ar², C₁₋₁₂alkyl, a radical of formula -Alk-R³, -Alk-Y-R⁴, -Alk-Z¹-C(X)-Z²-R⁵, or -CH₂-CHOH-CH₂-O-R⁶; the pharmaceutically acceptable acid addition salts and possible stereochemically isomeric forms thereof, which compounds are anti-­allergic agents; pharmaceutical compositions containing such compounds as an active ingredient and methods of preparing said compounds and pharmaceutical compositions.

  新颖的[(双环杂环)甲基和-杂环]取代的六氢-1H-氮杂卓和吡咯烷类，其式为 其中 -A¹=A²-A³=A⁴-是-CH=CH-CH=CH-、-N=CH-CH=CH-、-CH=N-CH=CH-、-CH=CH-N=CH-、-N=CH-N=CH-或-CH=N-CH=N-、 R¹ 是氢、C₁₋₁₀烷基、C₃₋₆环烷基、Ar¹ 或被一个或两个 Ar¹ 基取代的 C₁₋₆ 烷基； B 是 NR²、CH₂、O、S、SO 或 SO₂； R 是氢或 C₁₋₆ 烷基； n 为 0 或 2； L 是氢、C₁₋₆烷基羰基、C₁₋₆烷基磺酰基、C₁₋₆烷氧基羰基、Ar²-C₁₋₆烷氧基、Ar²-羰基、Ar²-磺酰基、C₃₋₆环烷基、任选被 Ar² 取代的 C₂₋₆烷基、C₁₋₁₂烷基、式-Alk-R³、-Alk-Y-R⁴、-Alk-Z¹-C(X)-Z²-R⁵或-CH₂-CHOH-CH₂-O-R⁶的基团； 药学上可接受的酸加成盐及其可能的立体化学异构形式，这些化合物是抗过敏剂；含有这些化合物作为活性成分的药物组合物以及制备所述化合物和药物组合物的方法。