5-nitro-2,2-dimethyl-2H-chromene | 82305-06-4

• 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: 5-nitro-2,2-dimethyl-2H-chromene
• 英文别名: 5-Nitro-2,2-dimethylchromene；2,2-Dimethyl-5-nitro-2H-1-benzopyran；2,2-dimethyl-5-nitrochromene
• CAS: 82305-06-4
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: CRICFSAKKLLSQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-nitro-2,2-dimethyl-2H-chromene 在 盐酸 、 tin 作用下， 以91%的产率得到5-amino-2,2-dimethyl-2H-chromene
  参考文献：
  名称：

  Brown, Philip E.; Lewis, Robert A., Journal of the Chemical Society. Perkin transactions I, 1992, # 5, p. 573 - 578

  摘要：

  DOI：
• 作为产物：
  描述：

  间硝基苯酚 在 吡啶 、 copper dichloride 作用下， 以 乙腈 为溶剂， 反应 17.17h， 生成 5-nitro-2,2-dimethyl-2H-chromene
  参考文献：
  名称：

  基于天然产物的杀菌剂：2H-色烯衍生物的合成及其对植物病原体的抗真菌活性

  摘要：

  为了寻找新的潜在抗真菌药物，设计、合成了40种 2 H-色烯类似物，并首次评价了它们对一些典型植物病原真菌的抗真菌活性。体外抗真菌生物测定表明，一些目标化合物表现出与商业农业杀真菌剂羟霉唑相当或更好的抑制活性。特别是化合物1m对Alternaria alternate (EC 50 =9.9 μg/mL)和Botrytis cinerea (EC 50 =9.4 μg/mL)表现出更好的杀菌效果，显着优于恶霉灵。此外，体内保护作用结果也表明，化合物1m具有作为新型植物源农药进一步开发的极好潜力。

  DOI：

  10.1002/cbdv.202200802

文献信息

• Synthesis and antihypertensive activity of substituted trans-4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ols
  作者：John M. Evans、Charles S. Fake、Thomas C. Hamilton、Robert H. Poyser、Eric A. Watts

  DOI：10.1021/jm00365a007

  日期：1983.11

  position. Exceptions to this were the 7-nitro-4-pyrrolidine analogue and the 6-nitro-3-chloropropylamine, which retained marked antihypertensive activity. All of these compounds were direct vasodilators and had comparable antihypertensive activity to hydralazine and to the calcium antagonist, nifedipine. The synthetic route to these compounds involves cyclization of of propargyl ethers to 2H-1-benzopyrans

  制备了一系列新型取代的反式-4-氨基-3,4-二氢-2,2-二甲基-2H-1-苯并吡喃-3-醇，并在有意识的乙酸脱氧皮质酮（DOCA）/盐水处理中测试了其降压活性。高血压大鼠。最佳的降血压活性需要一个强的吸电子基团与6位上的吡咯烷基或哌啶子基团一起进行6位取代。7-硝基-4-吡咯烷类似物和6-硝基-3-氯丙胺的例外，它们保留了明显的降压活性。所有这些化合物都是直接的血管扩张药，并且具有与肼屈嗪和钙拮抗剂硝苯地平相当的降压活性。这些化合物的合成路线包括将炔丙基醚环化为2H-1-苯并吡喃，然后通过溴代醇转化为3,4-环氧化物，用适当的胺开环。间取代的炔丙基醚在热环化反应中同时产生5-和7-取代的苯并吡喃，前者占优势。描述了一种新的制备2，2-二甲基-7-硝基苯并吡喃的途径。
• A New Preparative Method of 2,2-Dimethyl-2<i>H</i>-chromenes
  作者：Yoshiyuki Kawase、Seiji Yamaguchi、Hisanori Horita、Junko Takeno、Hideaki Kameyama

  DOI：10.1246/bcsj.55.1153

  日期：1982.4

  2,2-Dimethyl-2H-chromene was prepared from salicylaldehyde and ethyl 3-methyl-2-butenoate (or ethyl α-bromoisobutyrate) in one step. This new method of preparing 2,2-dimethyl-2H-chromene was studied and applied to some 2,2-dimethyl-2H-chromene derivatives.

  2,2-二甲基-2H-色烯由水杨醛和3-甲基-2-丁烯酸乙酯（或α-溴异丁酸乙酯）一步制备。研究了这种制备2,2-二甲基-2H-色烯的新方法并将其应用于一些2,2-二甲基-2H-色烯衍生物。
• Synthesis of 6-Cyano-2,2-dimethyl-2H-1-benzopyran and Other Substituted 2,2-Dimethyl-2H-1-benzopyrans
  作者：Jeffrey T. North、David R. Kronenthal、Annie J. Pullockaran、Sharon D. Real、Helen Y. Chen

  DOI：10.1021/jo00116a025

  日期：1995.6

  A practical synthesis of 6-cyano-2,2-dimethyl-2H-1-benzopyran (1) has been developed. This process involves the pyridine-catalyzed condensation of 1,1-diethoxy-3-methyl-2-butene (6) with 4-cyanophenol (3) in toluene or xylene at elevated temperatures. The development of this process, including an evaluation of solvents, bases, acid catalysts, and alternative acetals, along with an improved synthesis of 1,1-diethoxy-3-methyl-2-butene, is discus se d. Using this method, a variety of other substituted 2,2-dimethyl-2H-1-benzopyrans were synthesized.
• Continuous Processing to Control a Potentially Hazardous Process:  Conversion of Aryl 1,1-Dimethylpropargyl Ethers to 2,2-Dimethylchromenes (2,2-Dimethyl-2<i>H</i>-1-Benzopyrans)
  作者：Ricardo J. Bogaert-Alvarez、Paul Demena、Gus Kodersha、Robert E. Polomski、N. Soundararajan、Steve S. Y. Wang

  DOI：10.1021/op0100504

  日期：2001.11.1

  The thermal Claisen rearrangement of 4-cyanophenyl 1,1-dimethylpropargyl ether (4) to 6-cyano-2,2-dimethylchromene (5), (6-eyano-2,2-dimethyl-2H-1-benzopyran), which is used in the synthesis of a potassium channel activator drug candidate, BMS-180448, created a significant process development issue. The resulting large heat release in this conversion posed not only a safety risk but could also cause product degradation if done in a batch-wise manner. The solution was to exploit the high surface-to-volume ratio of a plug-flow reactor that would maximize the heat transfer, thereby permitting tight and responsive temperature with better reaction control. In the course of successfully testing the plug-flow concept on "micro"-flow scale (gram quantity) and "kilo"-flow scale (similar to 10 kg), a generalized mathematical model capable of predicting the reaction performance based on the physical properties of any given plug-flow reactor was generated. The model provides requisite information to design and operate a plug-flow reactor of any size for this reaction. This model would optimize reaction conditions for an acquired reactor system capable of producing similar to7 kg/h of the dimethylchromene. Application of plug-flow reactor technology enabled production of high quality 2,2-dimethylchromenes in good yield (> 98 mol %) without the use of solvents and with virtually no waste streams.
• KAWASE, YOSHIYUKI;YAMAGUCHI, SEIJI;HORITA, HISANORI;TAKENO, JUNKO;KAMEYAM+, BULL. CHEM. SOC. JAP., 1982, 55, N 4, 1153-1155
  作者：KAWASE, YOSHIYUKI、YAMAGUCHI, SEIJI、HORITA, HISANORI、TAKENO, JUNKO、KAMEYAM+

  DOI：——

  日期：——