2-amino-7,7-dimethyl-5-oxo-4-(3,4-methylenedioxyphenyl)-5,6,7,8-tetrahydro-4H-1-benzopyran-3-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-amino-7,7-dimethyl-5-oxo-4-(3,4-methylenedioxyphenyl)-5,6,7,8-tetrahydro-4H-1-benzopyran-3-carbonitrile
• 英文别名: 2-amino-4-(4-benzo[d][1,3]dioxol-5-yl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile；2-amino-4-(benzo[d][1,3]dioxol-5-yl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile；2-amino-4-(benzo[d][1,3]dioxol-5-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-3-cyano-7,7-dimethyl-4-(3,4-methylenedioxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-1-benzopyran；2-amino-4-(1,3-benzodioxol-5-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-4-(1,3-benzodioxol-5-yl)-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromene-3-carbonitrile
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: CIUUDCOYHBMQHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  94.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙醇 、 2-amino-7,7-dimethyl-5-oxo-4-(3,4-methylenedioxyphenyl)-5,6,7,8-tetrahydro-4H-1-benzopyran-3-carbonitrile 在 碘苯二乙酸 作用下， 以 水 为溶剂， 以80%的产率得到3-amino-4-(benzo[d][1,3]dioxol-5-yl)-2,2-dimethoxy-7,7-diethyl-5-oxo-3,4,5,6,7,8-hexahydro-2H-chromene-3-carbonitrile
  参考文献：
  名称：

  An Efficient Oxidative Difunctionalisation of 2-Amino-2H-chromene and Antimicrobial Activity of the Synthesized Tetrahydrochromene Derivatives

  摘要：

  A novel series of 3-amino-2,2-dialcoxy-7,7-dimethyl-5-oxo-4-phenyl-3,4,5,6,7,8-hexahydro-2H-chromene-3-carbonitriles are synthesized by oxidative difunctionalization (geminal dialkoxylation and migration of the amino group) of 2-amino-4-aryl-7,7-dimethyyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles in the presence of iodobenzenediacetate in water medium with excellent yields. All the newly synthesized compounds are characterized by IR, H-1 and C-13 NMR and Mass spectral data. The representative synthesized analogues are screened in vitro for antibacterial and antifungal activity using Gentamycin sulphate and Nystatin as standard drugs.

  DOI：

  10.1134/s1070363219050207
• 作为产物：
  描述：

  (苯并[3,4-d]1,3-二氧杂烷-5-亚甲基)甲烷-1,1-二甲腈 、 5,5-二甲基-1,3-环己二酮 在 巯基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到2-amino-7,7-dimethyl-5-oxo-4-(3,4-methylenedioxyphenyl)-5,6,7,8-tetrahydro-4H-1-benzopyran-3-carbonitrile
  参考文献：
  名称：

  用于合成新的4-氮杂芴酮衍生物的新型三组分反应

  摘要：

  使用微波加热成功地进行了亚芳基丙二腈，1，3-茚满二酮和巯基乙酸或4-甲基苯硫醇的反应。建立茚并吡啶骨架是一种有效而有前途的合成策略。

  DOI：

  10.1016/j.tet.2007.04.053

文献信息

• Uncatalyzed Reactions in Aqueous Media: Three-Component, One-Pot, Clean Synthesis of Tetrahydrobenzo[b]pyran Derivatives
  作者：Sunita B. Bandgar、Babasaheb P. Bandgar、Balaji L. Korbad、Jalinder V. Totre、Sachin Patil

  DOI：10.1071/ch06461

  日期：——

  The synthesis of various tetrahydrobenzo[b]pyran derivatives has been carried out by means of an uncatalyzed, three-component, one-pot clean condensation of aromatic aldehydes, reactive methylene compounds, and dimidone in aqueous medium. Simple workup, and mild and neutral conditions that give quantitative yields of products in pure form, are the attractive features of this method.

  各种四氢苯并[b]吡喃衍生物的合成是通过芳香醛、反应性亚甲基化合物和二米酮在水介质中的非催化、三组分、一锅清洁缩合进行的。简单的后处理，温和和中性的条件，可以定量获得纯产品的产量，是这种方法的吸引人的特点。
• Tris-hydroxymethylaminomethane (THAM): a novel organocatalyst for a environmentally benign synthesis of medicinally important tetrahydrobenzo[b]pyrans and pyran-annulated heterocycles
  作者：Kapil S. Pandit、Pramod V. Chavan、Uday V. Desai、Makarand A. Kulkarni、Prakash P. Wadgaonkar

  DOI：10.1039/c4nj02346c

  日期：——

  A simple, efficient and environmentally benign protocol has been developed for the one-pot, multicomponent synthesis of medicinally important tetrahydrobenzo[b]pyrans and pyran-annulated heterocycles using a commercially available, inexpensive, non-toxic, and biodegradable tris-hydroxymethylaminomethane (THAM) as a novel organocatalyst. Ambient reaction conditions, wide scope, avoidance of conventional

  已经开发了一种简单，有效且对环境无害的方案，用于使用市售，廉价，无毒且可生物降解的三羟甲基甲基甲烷（THAM）一锅，多组分合成重要的药用四氢苯并[ b ]吡喃和吡喃环杂环）作为新型有机催化剂。环境反应条件，宽范围，避免常规分离以及纯化技术以及催化剂连续五次运行的可重复使用性提高了该多组分反应规程歧管的实用性。
• Fluoride ion catalyzed multicomponent reactions for efficient synthesis of 4H-chromene and N-arylquinoline derivatives in aqueous media
  作者：Shijay Gao、Cheng Hsuan Tsai、Chi Tseng、Ching-Fa Yao

  DOI：10.1016/j.tet.2008.06.061

  日期：2008.9

  4H-Chromene and N-arylquinoline derivatives are obtained in good to excellent yields by proceeding through a simple, mild, and efficient procedure utilizing tetrabutylammonium fluoride (TBAF) as catalyst.

  通过使用氟化四丁基铵（TBAF）进行简单，温和和有效的程序，可以高至极好的收率获得4 H- Chromene和N-芳基喹啉衍生物。
• A Clean One-pot Synthesis of Tetrahydrobenzo[<i>b</i>]pyran Derivatives Catalyzed by Hexadecyltrimethyl Ammonium Bromide in Aqueous Media
  作者：Tong-Shou Jin、Ai-Qing Wang、Xin Wang、Jian-She Zhang、Tong-Shuang Li

  DOI：10.1055/s-2004-820025

  日期：——

  8-tetra-hydrobenzo[ b ]pyran derivatives using hexadecyltrimethyl ammoni-um bromide (HTMAB) as the catalyst (10 mol%) is described. Thismethod provides several advantages such as neutral conditions,high yields and simple work-up procedure, in addition water waschosen as a green solvent. Key words: tetrahydrobenzo[ b ]pyran, hexadecyltrimethyl ammo-nium bromide, aqueous media With increasing environmental

  摘要：一种高效便捷的合成2-氨基-3-氰基-4-芳基-7,7-二甲基-5-氧代-4 H-5,6,7,8-四氢苯并[b]吡喃的方法描述了使用十六烷基三甲基溴化铵 (HTMAB) 作为催化剂 (10 mol%) 的衍生物。该方法具有条件中性、收率高、后处理简单等优点，此外还选择了水作为绿色溶剂。关键词：四氢苯并[b]吡喃，十六烷基三甲基溴化铵，水性介质随着环境问题的日益严重，越来越多的化学家致力于“绿色合成”领域，这意味着试剂、溶剂和催化剂对环境友好。在现代有机化学研究中，文德将“理想合成”定义为目标成分一步生成，在资源有效且环境可接受的过程中，来自易得且廉价的起始材料的非定量产量。1 一锅多组分缩合代表了一种进行近乎理想合成的可能工具，因为它们具有上述特性之一，即以最大的简单性和简洁性构建复杂分子的可能性。
• A Facile and Efficient Synthesis of New Polysubstituted Indeno[1,2-<i>b</i>]pyri­dines via One-Pot, Three-Component Microwave-Assisted Reaction
  作者：Shujiang Tu、Bo Jiang、Junyong Zhang、Yan Zhang、Runhong Jia、Chunmei Li、Dianxiang Zhou、Longji Cao、Qingqing Shao

  DOI：10.1055/s-2007-967999

  日期：2007.2

  A rapid and efficient method is developed to synthesize new polysubstituted indeno[1,2-b]pyridines via three-component microwave-assisted reaction of arylidenemalononitrile, 1,3-indanedione and aromatic amine. This method has the advantages of short synthetic route, operational simplicity, increased safety for small-scale high-speed synthesis, and minimal environmental impact.

  开发了一种通过亚芳基丙二腈、1,3-茚二酮和芳香胺的三组分微波辅助反应合成新型多取代茚并[1,2-b]吡啶的快速有效方法。该方法具有合成路线短、操作简单、小规模高速合成安全性高、环境影响小等优点。