6-氯-3,4-二氢-2,2-二甲基-2H-1-苯并吡喃-4-酮 | 80055-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 6-氯-3,4-二氢-2,2-二甲基-2H-1-苯并吡喃-4-酮
• 英文名称: 6-chloro-2,2-dimethylchroman-4-one
• 英文别名: 6-Chloro-2,2-dimethyl-4-chromanone；6-chloro-2,2-dimethyl-3H-chromen-4-one
• CAS: 80055-85-2
• 化学式: C₁₁H₁₁ClO₂
• 分子量: 210.66
• InChiKey: OAQBJKPCYZKZJH-UHFFFAOYSA-N

物化性质

• 熔点：
  89-90 °C(Solv: ligroine (8032-32-4))
• 沸点：
  95-100 °C(Press: 0.2-0.3 Torr)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  6-氯-3,4-二氢-2,2-二甲基-2H-1-苯并吡喃-4-酮 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 6-chloro-2,2-dimethyl-2H-chromene
  参考文献：
  名称：

  Identification of 3-hydroxy-4[3,4-dihydro-3-oxo-2H-1,4-benzoxazin-4-yl]-2,2-dimethyldihydro-2H-benzopyran derivatives as potassium channel activators and anti-inflammatory agents

  摘要：

  The present study described the design, synthesis and identification of 3-hydroxy-4[3,4-dihydro-3-oxo-2H-1,4-benzoxazin-4-yl]-2,2-dimethyldihydro-2H-benzopyran derivatives. Their biological activity was tested for K-ATP channel opener as antihypertensives, COX-1 and COX-2 activity. The results were compared with the activity of cromakalim, ibuprofen and celecoxib. The study aimed at exploring the influence of introduction of a benzoxazine substituent at position 6 of various derivatives of benzopyrans in order to improve biological activity. Several compounds were found to be equipotent or even more potent than cromakalim. Out of these nitro-substituted benzopyrans, nitro substitution at benzoxazino group possessed potent antihypertensive activity in the R/S isomers. With amino derivatives, activity remains constant when compared with standard cromakalim. Similarly, compounds 17b, 17c, 17e and 17h have exhibited around 40 % inhibition of COX-1 as compared to the inhibition of COX-2. Only two compounds 17g and 17i exhibited effective inhibition more than 50 % of COX-2 compared with the inhibition of COX-1 at a concentration of 0.3 mg/ml.

  DOI：

  10.1007/s00044-015-1344-6
• 作为产物：
  描述：

  乙酸-4-氯苯酯 在 四氢吡咯 、 aluminum (III) chloride 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 6-氯-3,4-二氢-2,2-二甲基-2H-1-苯并吡喃-4-酮
  参考文献：
  名称：

  Identification of 3-hydroxy-4[3,4-dihydro-3-oxo-2H-1,4-benzoxazin-4-yl]-2,2-dimethyldihydro-2H-benzopyran derivatives as potassium channel activators and anti-inflammatory agents

  摘要：

  The present study described the design, synthesis and identification of 3-hydroxy-4[3,4-dihydro-3-oxo-2H-1,4-benzoxazin-4-yl]-2,2-dimethyldihydro-2H-benzopyran derivatives. Their biological activity was tested for K-ATP channel opener as antihypertensives, COX-1 and COX-2 activity. The results were compared with the activity of cromakalim, ibuprofen and celecoxib. The study aimed at exploring the influence of introduction of a benzoxazine substituent at position 6 of various derivatives of benzopyrans in order to improve biological activity. Several compounds were found to be equipotent or even more potent than cromakalim. Out of these nitro-substituted benzopyrans, nitro substitution at benzoxazino group possessed potent antihypertensive activity in the R/S isomers. With amino derivatives, activity remains constant when compared with standard cromakalim. Similarly, compounds 17b, 17c, 17e and 17h have exhibited around 40 % inhibition of COX-1 as compared to the inhibition of COX-2. Only two compounds 17g and 17i exhibited effective inhibition more than 50 % of COX-2 compared with the inhibition of COX-1 at a concentration of 0.3 mg/ml.

  DOI：

  10.1007/s00044-015-1344-6

文献信息

• Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight
  作者：Daniela Iguchi、Rosa Erra-Balsells、Sergio M. Bonesi

  DOI：10.1016/j.tet.2016.02.039

  日期：2016.4

  Several aryl 3-methyl-2-butenoate esters upon irradiation lead to the formation of [1,3]-migrated photoproducts, phenol and, surprisingly 2,2-dimethylchroman-4-one derivatives. The starting photochemical reaction takes place from the singlet excited state of the ester and as a total mechanism two consecutive reaction pathways are proposed. The former involves the photo-Fries rearrangement of the esters

  辐照后的几种芳基3-甲基-2-丁烯酸酯会导致[1,3]迁移的光产物，苯酚以及令人惊讶的2,2-二甲基苯并吡喃-4-酮衍生物的形成。起始光化学反应从酯的单重激发态发生，并且作为总机理，提出了两个连续的反应途径。前者涉及酯在所有研究的溶剂中的光-弗里斯重排，并且取决于溶剂的质子性，后者涉及ESIPT过程，然后进行热6π-电环反应和/或热（分子内氧杂-迈克尔加成反应）邻位区域异构体的环化形成。该第二途径负责2，2-二甲基苯并吡喃-4-酮衍生物的形成。
• Facile Deoxygenation of Hydroxylated Flavonoids by Palladium-Catalysed Reduction of its Triflate Derivatives
  作者：József Kövér、Sándor Antus

  DOI：10.1515/znb-2005-0716

  日期：2005.7.1

  An efficient procedure to deoxygenate hydroxy substituted flavonoids, isoflavonoids and related compounds via their trifluoromethanesulfonates is presented. Their reduction with formic acid in the presence of a catalytic amount of palladium acetate, triethylamine and 1,3-bis(diphenylphosphanyl) propane (dppp) in DMF results in their des-hydroxy derivatives without affecting other functional groups.

  通过使用三氟甲磺酸盐，以催化量的乙酸钯、三乙胺和1,3-双(二苯基膦基)丙烷（dppp）在DMF中，将含羟基的黄酮类化合物、异黄酮类化合物及相关化合物脱氧的高效程序被提出。在甲酸存在下，它们的还原会导致它们的去羟基衍生物，而不影响其他功能团。
• A simple route for the synthesis of 4-chlorochromenes and chroman-4-ones
  作者：G. Ariamala、K.K. Balasubramanian

  DOI：10.1016/0040-4039(88)85197-9

  日期：1988.1

  A one pot synthesis of a number of 4-chlorochromenes and chroman-4-ones was achieved from γ-chloropropargyl aryl ethers proceeding through Claisen rearrangement, depending upon the solvent of choice.

  根据选择的溶剂，通过克莱森重排，由γ-氯炔丙基芳基醚进行一锅合成多个4-氯苯并二氢吡喃和苯并吡喃-4-酮。
• Thermal behaviour of aryl γ-haloprcpargyl ethers
  作者：G. Ariamala、K.K. Balasubramanian

  DOI：10.1016/0040-4020(89)80058-4

  日期：1989.1

  A systematic study of the behaviour of aryl γ-halopropargyl ethers under thermal condition was undertaken. Aryl γ-bromopropargyl ethers underwent unique transformation in N,N-diethylanillne (215°C, 6 h) giving rise to a mixture of products ,and , whereas, under similar conditions aryl γ-chloropropargyl ethers ulbar|8, afforded 4-chlorochromenes, 9. A remarkable substituent and solvent effect has been

  对芳基γ-卤代炔丙基醚在热条件下的行为进行了系统的研究。芳基γ-溴代炔丙基醚类的N，N-二diethylanillne（215℃，6小时）引起的产物的混合物进行独特变换，并且，反之，在类似条件下芳基γ-chloropropargyl醚ulbar | 8，得到4- chlorochromenes ，9。在这些芳基γ-溴和γ-氯炔丙基醚的热解中观察到了显着的取代基和溶剂作用，从而使这种转化成为合成许多取代的4-溴色烯，4-氯色烯和chroman-4-ones 。相反，芳基γ-碘炔丙基醚的溶液热解得到芳基炔丙基醚。 作为主要产品。
• Synthesis and reactions of some chloro-2,2-dimethylchromens
  作者：John D. Hepworth、Terry K. Jones、Robert Livingstone

  DOI：10.1016/s0040-4020(01)98965-3

  日期：1981.1

  5-, 6-, 7-, and 8-Chloro-2,2-dimethylchromins have been prepared from the corresponding chloro-coumarin and their conversion into the 3,4-dihalogenochroman derivatives is described. The 4-halogen atom is shown to be the more susceptible to hydrolysis by conversion of the resulting halohydrins into chromanones and epoxides. The formation of bis-chromens during the dehalogenation of 3-halogenochromanones

  已经从相应的氯香豆素制备了5-，6-，7-和8-氯-2,2-二甲基苯并二恶英，并描述了它们向3,4-二卤代苯并二氢吡喃衍生物的转化。通过将产生的卤代醇转化成苯并二氢吡喃酮和环氧化物，显示4-卤素原子更易于水解。据报道在3-卤代铬烷酮的脱卤过程中双铬的形成。