6-bromo-2,2,3-trimethyl-2H-benzo[b]pyran | 148430-51-7

• 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: 6-bromo-2,2,3-trimethyl-2H-benzo[b]pyran
• 英文别名: 6-bromo-2,2,3-trimethyl-2H-benzopyran；6-bromo-2,2,3-trimethyl-2H-1-benzopyran；6-bromo-2,2,3-trimethylchromene
• CAS: 148430-51-7
• 化学式: C₁₂H₁₃BrO
• 分子量: 253.139
• InChiKey: UXGHGDOILCOQMW-UHFFFAOYSA-N

物化性质

• 沸点：
  298.0±40.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-bromo-2,2,3-trimethyl-2H-benzo[b]pyran 在 溴 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以68%的产率得到3,4,6-tribromo-3,4-dihydro-2,2,3-trimethyl-2H-benzopyran
  参考文献：
  名称：

  Cotterill, W. David; Livingstone, Robert; O'Donnell, Patrick A., Journal of Chemical Research, Miniprint, 1993, # 11, p. 3001 - 3007

  摘要：

  DOI：
• 作为产物：
  描述：

  6-bromo-2,2,3-trimethyl-4-hydroxy-3,4-dihydro-2H-1-benzopyran 在 对甲苯磺酸 作用下， 生成 6-bromo-2,2,3-trimethyl-2H-benzo[b]pyran
  参考文献：
  名称：

  钾通道开放剂 (3S,4R)-3,4-Dihydro-4-(2,3-dihydro-2-methyl-3-oxo-pyridazin-6-Yl)oxy-3-hydroxy-6-( 3-羟基苯基)磺酰基-2,2,3-三甲基-2H-苯并[b]吡喃

  摘要：

  摘要 钾通道开放剂 (3S,4R)-3,4-dihydro-4-(2,3-dihydro-2-methyl-3-oxo-pyridazin-6-yl)oxy-3-hydroxy-6 的制备报道了-(3-羟基苯基)磺酰基-2,2,3-三甲基-2H-苯并[b]吡喃(1)作为单一对映异构体。相对于原始合成进行了相当大的改进，允许制备数克数量的最终目标化合物。优化的合成由六步线性序列组成，其关键步骤是通过使用 Jacobsen's (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene) 的不对称环氧化方案)-1,2-环己烷二氨基锰(III)氯化物催化剂。

  DOI：

  10.1080/00397910701557531

文献信息

• Novel benzopyran derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05447943A1

  公开（公告）日：1995-09-05

  Compounds of the Formula: ##STR1## wherein: R.sup.1-7 are as defined in the specification. The compounds and salts exhibit useful pharmacological properties, including potassium channel activating properties and 5-lipoxygenase inhibiting properties, and in particular are useful as smooth muscle relaxants and bronchodilators.

  式中的化合物：##STR1## 其中：R.sup.1-7 如规范中所定义。这些化合物和盐表现出有用的药理特性，包括钾通道激活特性和5-脂氧合酶抑制特性，特别是作为平滑肌松弛剂和支气管扩张剂时非常有用。
• Benzopyrans
  申请人：Pfizer Inc.

  公开号：US05912244A1

  公开（公告）日：1999-06-15

  A compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof, wherein X is O, S or NH; R and R.sup.1 are each independently selected from H and C.sub.1 -C.sub.4 alkyl or taken together represent C.sub.2 -C.sub.6 alkylene; R.sup.2 is H or C.sub.1 -C.sub.4 alkyl; R.sup.3 is a 6-membered heterocyclic ring containing 2N hetero-atoms, said ring being linked to X by a ring carbon atom, optionally benzo-fused and optionally substituted, including in the benzo-fused portion, by C.sub.1 -C.sub.6 alkyl, hydroxy, --OR.sup.5, halo, --S(O).sub.m R.sup.5, oxo, amino, --NHR.sup.5, --N(R.sup.5).sub.2, cyano, --CO.sub.2 R.sup.5, --CONH.sub.2, --CONHR.sup.5 or --CON(R.sup.5).sub.2, with the proviso that R.sup.3 is not an N--(C.sub.1 -C.sub.6 alkyl)pyridonyl group; R.sup.4 is phenyl substituted by a hydroxy group and optionally further substituted by 1 or 2 substitutents each independently selected from hydroxy, C.sub.1 -C.sub.6 alkyl, --OR.sup.5, halo, cyano and nitro; R.sup.5 is C.sub.1 -C.sub.6 alkyl; R.sup.6 is --OR.sup.5, --NHR.sup.5, --N(R.sup.5).sub.2, --SR.sup.5 or --NHR.sup.9 ; R.sup.7 is cyano; R.sup.8 is --OR.sup.5, --NHR.sup.5, --N(R.sup.5).sub.2, or --NHR.sup.9 ; R.sup.9 is phenyl optionally substituted by C.sub.1 -C.sub.6 alkyl, hydroxy, --OR.sup.5, halo, cyano or nitro; and m is 0, 1 or 2.

  该化合物的结构式为：##STR1##或其药学上可接受的盐，其中X为O、S或NH；R和R.sup.1分别独立选择自H和C.sub.1-C.sub.4烷基，或者一起代表C.sub.2-C.sub.6烷基；R.sup.2为H或C.sub.1-C.sub.4烷基；R.sup.3为含有2N杂原子的6元杂环，该环通过一个环碳原子与X连接，可选择地苯并联和可选择地被C.sub.1-C.sub.6烷基、羟基、--OR.sup.5、卤素、--S(O).sub.mR.sup.5、酮基、氨基、--NHR.sup.5、--N(R.sup.5).sub.2、氰基、--CO.sub.2R.sup.5、--CONH.sub.2、--CONHR.sup.5或--CON(R.sup.5).sub.2取代，条件是R.sup.3不是N--(C.sub.1-C.sub.6烷基)吡啶基；R.sup.4为苯基，被羟基取代，可选择地进一步被独立选择自羟基、C.sub.1-C.sub.6烷基、--OR.sup.5、卤素、氰基和硝基的1或2个取代基取代；R.sup.5为C.sub.1-C.sub.6烷基；R.sup.6为--OR.sup.5、--NHR.sup.5、--N(R.sup.5).sub.2、--SR.sup.5或--NHR.sup.9；R.sup.7为氰基；R.sup.8为--OR.sup.5、--NHR.sup.5、--N(R.sup.5).sub.2或--NHR.sup.9；R.sup.9为苯基，可选择地被C.sub.1-C.sub.6烷基、羟基、--OR.sup.5、卤素、氰基或硝基取代；m为0、1或2。
• Benzopyran derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05250547A1

  公开（公告）日：1993-10-05

  Compounds of the Formula: ##STR1## wherein: R.sup.1 and R.sup.2 are independently hydrogen or lower alkyl, or when taken together with the carbon to which they are attached are cycloalkyl of 3 to 8 carbon atoms; R.sup.3 is fluoro lower alkyl; cyano; or nitro; R.sup.4 is ##STR2## R.sup.5 and R.sup.6 are independently hydrogen or lower alkyl; and R.sup.7 is --NR.sup.8 R.sup.9 ; wherein: R.sup.8 is hydrogen; lower alkyl; lower alkoxy; hydroxy; or hydroxy lower alkyl; and R.sup.9 is hydrogen; lower alkyl; hydroxy lower alkyl; --SO.sub.2 R.sup.10 ; --CO.sub.2 R.sup.10 ; --C(O)NR.sup.11 R.sup.12 ; --C(S)NR.sup.11 R.sup.12 ; or --C(O)R.sup.12 ; wherein R.sup.10 is lower alkyl; R.sup.11 is hydrogen or lower alkyl; and R.sup.12 is hydrogen, lower alkyl, or fluoro lower alkyl; with the proviso that R.sup.8 and R.sup.9 cannot both be hydrogen; and the pharmaceutically acceptable salts thereof. The compounds and salts exhibit useful pharmacological properties, including potassium channel activating properties and 5-lipoxygenase inhibiting properties, and in particular are useful as smooth muscle relaxants and bronchodilators.

  该公式化合物如下：##STR1## 其中：R.sup.1和R.sup.2独立地为氢或低碳基，或者与它们连接的碳一起形成3到8个碳原子的环烷基；R.sup.3为氟代低碳基；氰基；或硝基；R.sup.4为##STR2## R.sup.5和R.sup.6独立地为氢或低碳基；R.sup.7为--NR.sup.8 R.sup.9；其中：R.sup.8为氢；低碳基；低烷氧基；羟基；或羟基低碳基；R.sup.9为氢；低碳基；羟基低碳基；--SO.sub.2 R.sup.10 ；--CO.sub.2 R.sup.10 ；--C(O)NR.sup.11 R.sup.12 ；--C(S)NR.sup.11 R.sup.12 ；或--C(O)R.sup.12 ；其中R.sup.10为低碳基；R.sup.11为氢或低碳基；R.sup.12为氢、低碳基或氟代低碳基；但是R.sup.8和R.sup.9不能同时为氢；以及其药学上可接受的盐。这些化合物和盐具有有用的药理学特性，包括钾通道激活特性和5-脂氧合酶抑制特性，特别是作为平滑肌松弛剂和支气管扩张剂时非常有用。
• Benzopyran derivatives as potassium channel activators and 5-lipoxygenase inhibitors
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0529654A1

  公开（公告）日：1993-03-03

  Compounds of the Formula: wherein: R¹ and R² areindependently hydrogen or lower alkyl, or when taken together with the carbon to which they are attached are cycloalkyl of 3 to 8 carbon atoms; R³ ishydrogen, halo, fluoro lower alkyl, cyano, or nitro; R⁴ is R⁵ and R⁶ areindependently hydrogen or lower alkyl; and R⁷ is-NR⁸R⁹; wherein: R⁸ ishydrogen; lower alkyl; lower alkoxy; hydroxy; or hydroxy lower alkyl; and R⁹ ishydrogen; lower alkyl; hydroxy lower alkyl; -SO₂R¹⁰; -CO₂R¹⁰; -C(O)NR¹¹R¹²; -C(S)NR¹¹R¹²; or -C(O)R¹²; wherein R¹⁰ islower alkyl; R¹¹ ishydrogen or lower alkyl; and R¹² ishydrogen, lower alkyl, or fluoro lower alkyl; with the proviso that R⁸ and R⁹ cannot both be hydrogen; and the pharmaceutically acceptable salts thereof. The compounds and salts exhibit useful pharmacological properties, including potassium channel activating properties and 5-lipoxygenase inhibiting properties, and in particular are useful as smooth muscle relaxants and bronchodilators.

  式的化合物： 其中 R¹ 和 R² 分别为氢或低级烷基，或与所连接的碳一起为 3 至 8 个碳原子的环烷基； R³ 是氢、卤素、氟低级烷基、氰基或硝基； R⁴ 是 R⁵ 和 R⁶ 分别是氢或低级烷基；以及 R⁷ 是-NR⁸R⁹；其中 R⁸ 是氢；低级烷基；低级烷氧基；羟基；或羟基低级烷基；和 R𠞙 是氢；低级烷基；羟基低级烷基；-SO₂R¹⁰；-CO₂R¹⁰；-C(O)NR¹R¹²；-C(S)NR¹R¹²；或 -C(O)R¹²；其中 R¹⁰ 是低级烷基； R¹¹ 是氢或低级烷基；以及 R¹² 是氢、低级烷基或氟低级烷基； 但 R⁸ 和 R𠞙 不能都是氢；及其药学上可接受的盐。这些化合物和盐具有有用的药理特性，包括钾通道激活特性和 5-脂氧合酶抑制特性，特别是可用作平滑肌松弛剂和支气管扩张剂。
• BENZOPYRANES AS POTASSIUM CHANNEL OPENERS
  申请人：Pfizer Limited

  公开号：EP0690855B1

  公开（公告）日：1996-12-18