2-amino-3-cyano-4-(3,4-dioxymethylenephenyl)-4H-benzochromene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-amino-3-cyano-4-(3,4-dioxymethylenephenyl)-4H-benzochromene
• 英文别名: 2-Amino-4-(3,4-methylenedioxyphenyl)-4H-naphtho[1,2-b]pyran-3-carbonitrile；2-amino-4-(1,3-benzodioxol-5-yl)-4H-benzo[h]chromene-3-carbonitrile
• 化学式: C₂₁H₁₄N₂O₃
• 分子量: 342.354
• InChiKey: QEEUJPYNXNOABM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  胡椒醛 、 萘酚 、 丙二腈 在 四丁基溴化铵 作用下， 以 水 为溶剂， 反应 6.0h， 以88%的产率得到2-amino-3-cyano-4-(3,4-dioxymethylenephenyl)-4H-benzochromene
  参考文献：
  名称：

  An Efficient and Convenient Approach to the Synthesis of Benzopyrans by a Three-Component Coupling of One-Pot Reaction

  摘要：

  描述了一种通用且实用的化学合成路线，利用四丁基溴化铵（TBABr）作为催化剂（10 mol%）合成多功能化的苯并吡喃。该方法具有几项优点，如中性条件、高产率和简单的后处理程序。此外，水被选择作为绿色溶剂。

  DOI：

  10.1055/s-2003-42030

文献信息

• Clean, One‐Pot Synthesis of Naphthopyran Derivatives in Aqueous Media
  作者：Tong‐Shou Jin、Jian‐She Zhang、Li‐Bin Liu、Ai‐Qing Wang、Tong‐Shuang Li

  DOI：10.1080/00397910600632096

  日期：2006.6

  Abstract A general and practical one‐pot synthesis of naphthopyran derivatives using hexadecyltrimethylammonium bromide (HTMAB) as catalyst (10 mol%) is described. This method provides several advantages such as neutral conditions, high yields and simple workup procedure. The catalyst is low cost, facile, active, environmentally friendly, and reusable. In addition, water is chosen as a green solvent

  摘要描述了使用十六烷基三甲基溴化铵 (HTMAB) 作为催化剂 (10 mol%) 的通用和实用的萘并吡喃衍生物的一锅法合成。这种方法提供了几个优点，例如中性条件、高产率和简单的后处理程序。该催化剂成本低、操作简便、活性高、环境友好、可重复使用。此外，选择水作为绿色溶剂。
• Exploitation of the catalytic efficacy of Mg/Al hydrotalcite for the rapid synthesis of 2-aminochromene derivatives via a multicomponent strategy in the presence of microwaves
  作者：Mandar P. Surpur、Siddheshwar Kshirsagar、Shriniwas D. Samant

  DOI：10.1016/j.tetlet.2008.11.114

  日期：2009.2

  Mg/Al hydrotalcite, a heterogeneous base catalyst, was found to be highly effective for the synthesis of 2-aminochromenes via a multicomponent reaction of aromatic aldehydes, malononitriles and 1-naphthol under microwaves. The reaction is rapid, clean and gives the products in high yields. The catalyst is reusable; however, there was reduction in the yield of the product.

  发现Mg / Al水滑石是一种非均相基础催化剂，在微波下通过芳族醛，丙二腈和1-萘酚的多组分反应，对合成2-氨基色酮非常有效。该反应是快速，清洁的，并以高收率得到产物。催化剂可重复使用；但是，产物的收率降低了。
• Antiproliferative derivatives of 4H-naphtho 1,2-b pyran
  申请人：LILLY INDUSTRIES LIMITED

  公开号：EP0537949A1

  公开（公告）日：1993-04-21

  A pharmaceutical compound of the formula in which n is 0, 1 or 2 and R¹ is attached at any of the positions 5, 6, 7, 8, 9 or 10, and each R¹ is halo, trifluoromethyl, C₁₋₄ alkoxy, hydroxy, nitro, C₁₋₄ alkyl, C₁₋₄ alkylthio, hydroxy-C₁₋₄ alkyl, hydroxy-C₁₋₄ alkoxy, trifluoromethoxy, carboxy, -COOR⁵ where R⁵ is an ester group, -CONR⁶R⁷ or -NR⁶R⁷ where R⁶ and R⁷ are each hydrogen or C₁₋₄alkyl;    R² is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofurangyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R² is furanyl optionally substituted with C₁₋₄ alkyl;    R³ is nitrile, carboxy, -COOR⁸ where R⁸ is an ester group, -CONR⁹R¹⁰ where R⁹ and R¹⁰ are each hydrogen or C₁₋₄ alkyl, or R¹¹SO₂- where R¹¹ is C₁₋₄ alkyl or optionally substituted phenyl; and    R⁴ is -NR¹²R¹³, -NHCOR¹², -N(COR¹²)₂ or -N=CHOCH₂R¹² where R¹² and R¹³ are each hydrogen or C₁₋₄ alkyl optionally substituted with carboxy, where X is C₂₋₄ alkylene, or -NHSO₂R¹⁴ where R¹⁴ is C₁₋₄ alkyl or optionally substituted phenyl;    provided that when n is 0, R³ is nitrile and R⁴ is -NH₂, R² is not phenyl or phenyl substituted in the para-position with a single chloro, hydroxy or methoxy substituent;    and salts thereof.

  一种药物化合物，其化学式为 其中 n 为 0、1 或 2，R¹ 连接在位置 5、6、7、8、9 或 10 中的任一位置，且每个 R¹ 为卤代、三氟甲基、C₁₋₄烷氧基、羟基、硝基、C₁₋₄烷基、C₁₋₄烷硫基、羟基-C₁₋₄ 烷基、羟基-C₁₋₄ 烷氧基、三氟甲氧基、羧基、-COOR⁵（其中 R⁵ 是酯基）、-CONR⁶R⁷ 或-NR⁶R⁷（其中 R⁶ 和 R⁷ 各为氢或 C₁₋₄烷基）； R²是苯基、萘基或选自噻吩基、吡啶基、苯并噻吩基、喹啉基、苯并呋喃基或苯并咪唑基的杂芳基，所述苯基、萘基和杂芳基被任选取代，或 R² 是被 C₁₋₄ 烷基任选取代的呋喃基； R³ 是腈、羧基、-COOR⁸（其中 R⁸ 是酯基）、-CONR⁹R¹⁰（其中 R⁹ 和 R¹⁰ 分别是氢或 C₁₋₄ 烷基）或 R¹SO₂-（其中 R¹ 是 C₁₋₄ 烷基或任选取代的苯基）；以及 R⁴是-NR¹²R¹³、-NHCOR¹²、-N(COR¹²)₂或-N=CHOCH₂R¹²，其中 R¹² 和 R¹³ 分别是氢或任选被羧基取代的 C₁₋₄ 烷基、 其中 X 是 C₂₋₄亚烷基，或 -NHSO₂R¹⁴ 其中 R¹⁴ 是 C₁₋₄ 烷基或任选被取代的苯基； 但当 n 为 0，R³ 为腈且 R⁴ 为 -NH₂ 时，R² 不是苯基或在对位被单个氯、羟基或甲氧基取代的苯基； 及其盐类。
• Pharmaceutical compounds
  申请人：LILLY INDUSTRIES LIMITED

  公开号：EP0618206A1

  公开（公告）日：1994-10-05

  The invention provides pharmaceutical compounds of the formula: in which A --- B is CH₂-CH₂ or CH=CH; X is a pyridine or benzene ring; when X is pyridine n is 0; when X is benzene n is 0, 1 or 2 and when A --- B is CH₂-CH₂, R¹ is attached at any of the positions 7 to 10, and when A --- B is CH=CH, R¹ is attached at any of the positions 5 to 10; each R¹ is halo, carboxy, trifluoromethyl, hydroxy, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ alkylthio, hydroxy-C₁₋₄ alkyl, hydroxy-C₁₋₄ alkoxy, nitrogen-containing heterocyclyl, nitro, trifluoromethoxy, -COOR⁵ where R⁵ is an ester group, -COR⁶, -CONR⁶R⁷ or -NR⁶R⁷ where R⁶ and R⁷ are each hydrogen or C₁₋₄ alkyl; R² is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R² is furanyl optionally substituted with C₁₋₄ alkyl; R³ is nitrile, carboxy, -COOR⁸ where R⁸ is an ester group, -CONR⁹R¹⁰ where R⁹ and R¹⁰ are each hydrogen or C₁₋₄ alkyl, or -SO₂R¹¹ where R¹¹ is C₁₋₄ alkyl, optionally substituted phenyl or optionally substituted phenyl-C₁₋₄ alkyl; and R⁴ is 1-pyrrolyl, 1-imidazolyl or 1-pyrazolyl, said 1-pyrrolyl, 1-imidazolyl and 1-pyrazolyl being optionally substituted by one or two C₁₋₄ alkyl, carboxyl, hydroxy-C₁₋₄ alkyl or -CHO groups, or 1-(1,2,4-triazolyl), 1-(1,3,4-triazolyl) or 2-(1,2,3-triazolyl), said triazolyl groups being optionally substituted by a C₁₋₄ alkyl or C₁₋₄ perfluoroalkyl group, or 1-tetrazolyl optionally substituted by C₁₋₄ alkyl; and salts thereof.

  本发明提供了式中的药物化合物： 其中 A --- B 是 CH₂-CH₂ 或 CH=CH； X 是吡啶或苯环； 当 X 为吡啶时 n 为 0； 当X为苯时，n为0、1或2；当A--B为CH₂-CH₂时，R¹连接在7至10的任一位置；当A--B为CH＝CH时，R¹连接在5至10的任一位置； 每个 R¹ 是卤代、羧基、三氟甲基、羟基、C₁₋₄ 烷基、C₁₋₄ 烷氧基、C₁₋₄ 烷硫基、羟基-C₁₋₄ 烷基、羟基-C₁₋₄ 烷氧基、含氮杂环基、硝基、三氟甲氧基、-COOR⁵（其中 R⁵ 是酯基）、-COR⁶、-CONR⁶R⁷ 或-NR⁶R⁷（其中 R⁶ 和 R⁷ 各为氢或 C₁₋₄ 烷基）； R² 是苯基、萘基或选自噻吩基、吡啶基、苯并噻吩基、喹啉基、苯并呋喃基或苯并腙唑基的杂芳基，所述苯基、萘基和杂芳基被任选取代，或 R² 是被 C₁₋₄ 烷基任选取代的呋喃基； R³ 是腈、羧基、-COOR⁸（其中 R⁸ 是酯基）、-CONR⁹R¹⁰（其中 R⁹ 和 R¹⁰ 分别是氢或 C₁₋₄ 烷基）或-SO₂₋₄烷基、或-SO₂R¹¹，其中 R¹¹ 是 C₁₋₄烷基、任选取代的苯基或任选取代的苯基-C₁₋₄烷基；和 R⁴ 是 1-吡咯基、1-咪唑基或 1-吡唑基，所述 1-吡咯基、1-咪唑基和 1-吡唑基可任选被一个或两个 C₁₋₄烷基、羧基、羟基-C₁₋₄烷基或 -CHO 基团取代，或 1-(1,2、1-(1,2,3,4-三唑基)、1-(1,3,4-三唑基)或 2-(1,2,3-三唑基)，所述三唑基可选择被 C₁₋₄烷基或 C₁₋₄全氟烷基取代，或可选择被 C₁₋₄烷基取代的 1-四唑基； 及其盐类。
• Synthesis of 2‐Aminochromene Derivatives Catalyzed by KF/Al₂O₃
  作者：Xiang‐shan Wang、Da‐qing Shi、Hui‐zhen Yu、Gao‐feng Wang、Shu‐jiang Tu

  DOI：10.1081/scc-120027291

  日期：2004.12.31

  A series of 2-aminochromene derivatives include 2-aminobenzo-[h]chromene and naphtha[1,2-b;6.5-b']dipyrans derivatives were synthesized from arylaidehyde, malononitrile or ethyl cyanoacetate, with 1-naphthol or 1,5-naphthalenediol in refluxing ethyl alcohol catalyzed by KF-Al2O3. The structure of the products was confirmed by X-ray analysis.