6-hydroxymethyl-2,2-dimethyl-2H-chromene | 82441-64-3

• 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-hydroxymethyl-2,2-dimethyl-2H-chromene
• 英文别名: (2,2-dimethyl-2H-chromen-6-yl)methanol；2,2-dimethyl-6-hydroxymethylchromene；eulatachromene；6-hydroxymethyl-2,2-dimethyl-(2H)-chromene；(2,2-Dimethylchromen-6-yl)methanol
• CAS: 82441-64-3
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: QNBPDVUHGIPLIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-hydroxymethyl-2,2-dimethyl-2H-chromene 在 氯化亚砜 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 6-chloromethyl-2,2-dimethyl-(2H)-chromene
  参考文献：
  名称：

  Pesticidal chromen-6-yl-methyl-oxy-and-thiapyrizinones

  摘要：

  该公式中的杀虫剂取代吡啶酮为##STR1## 其中R.sup.1代表烷基，卤代烷基，烷氧基烷基，烷硫基烷基，（二）烷基氨基烷基，烯基或卤代烯基，或在每种情况下代表可选择取代的环烷基，环烷基烷基，芳基或芳基烷基。R.sup.2代表卤素或烷基，R.sup.3和R.sup.4分别独立地代表氢或烷基，R.sup.5和R.sup.6代表氢，羧基，每种情况下可选择取代的直链或支链烷基，烯基，烷氧羰基，芳基或芳基烷基，或者与它们所结合的碳原子一起，代表一个可选择取代的饱和或不饱和碳环。R.sup.7，R.sup.8，R.sup.9，R.sup.10和R.sup.11分别独立地代表氢，卤素，烷基，卤代烷基，烷氧基，卤代烷氧基，烷硫基或卤代烷硫基，X代表氧或硫。其中还有几种新的中间体。

  公开号：

  US05141939A1
• 作为产物：
  描述：

  对羟基苯甲醇 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基苯胺 、 丙酮 为溶剂， 反应 76.0h， 生成 6-hydroxymethyl-2,2-dimethyl-2H-chromene
  参考文献：
  名称：

  Asymmetric Epoxidation of Alkenes Catalyzed by a Porphyrin-Inspired Manganese Complex

  摘要：

  A novel strategy for catalytic asymmetric epoxidation of a wide variety of olefins by a porphyrin-inspired chiral manganese complex using H2O2 as a terminal oxidant in excellent yield with up to greater than 99% ee has been successfully developed.

  DOI：

  10.1021/ol401812h

文献信息

• Microwave-assisted palladium mediated decarbonylation reaction: synthesis of eulatachromene
  作者：Akanksha、Debabrata Maiti

  DOI：10.1039/c2gc35622h

  日期：——

  Microwave-assisted decarbonylation reactions were investigated using a palladium catalyst. A large number of aldehydes can be decarbonylated efficiently with lower catalyst loadings and under shorter reaction times compared to conventional heating. A successful decarbonylation led to the synthesis of natural product eulatachromene in three steps starting from easily available materials.

  通过使用钯催化剂，对微波辅助脱羰反应进行了研究。与传统加热方式相比，许多醛类可以在较低的催化剂用量和较短的反应时间内高效地进行脱羰反应。成功的脱羰反应使得从易得原料出发，通过三个步骤合成了天然产物eulatachromene。
• Thieme Chemistry Journal Awardees - Where Are They Now? Microwave-Assisted Rhodium-Catalyzed Decarbonylation of Functionalized 3-Formyl-2<i>H</i>-chromenes: A Sequence for Functionalized Chromenes like Deoxycordiachromene
  作者：Stefan Bräse、Manuel Bröhmer、Nicole Volz

  DOI：10.1055/s-0029-1217179

  日期：——

  3-Formyl-2H-chromenes which are readily accessible through an oxa-Michael reaction of salicylaldehydes and α,β-unsaturated aldehydes undergo a smooth decarbonylation reaction upon treatment with rhodium catalysts. With our method, a great variety of functionalized chromenes is accessible in a two-step sequence from salicylaldehydes.

  3-甲酰基-2H-色烯可通过水合物迈克尔反应，由水杨醛和α，β-不饱和醛轻易制得。这些化合物在铑催化剂作用下会顺利进行脱羰反应。运用我们的方法，可通过水杨醛的两步反应，大量制备功能化色烯。
• Substituierte Pyridazinone, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel
  申请人：BAYER AG

  公开号：EP0453837A2

  公开（公告）日：1991-10-30

  Es werden neue substituierte Pyridazinone der allgemeinen Formel (I), bereitgestellt, in welcher R¹für Alkyl, Halogenalkyl, Alkoxyalkyl, Alkylthioalkyl, (Di)alkylaminoalkyl, Alkenyl, Halogenalkenyl, für jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl, Aryl oder Aralkyl steht, R²für Halogen oder Alkyl steht, R³ und R⁴unabhängig voneinander jeweils für Wasserstoff oder Alkyl stehen, R⁵ und R⁶für Wasserstoff, Carboxy, jeweils gegebenenfalls substituiertes, geradkettiges oder verzweigtes Alkyl, Alkenyl, Alkoxycarbonyl, Aryl, Aralkyl oder gemeinsam mit dem Kohlenstoffatom, an das sie gebunden sind, für einen gegebenenfalls substituierten gesättigten oder ungesättigten Carbocyclus stehen, R⁷, R⁸, R⁹, R¹⁰ und R¹¹unabhängig voneinander jeweils für Wasserstoff, Halogen, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkylthio oder Halogenalkylthio stehen und Xfür Sauerstoff oder Schwefel steht. Die neuen Verbindungen der Formel (I) besitzen eine stark ausgeprägte Wirksamkeit gegen Schädlinge, insbesondere eine gute insektizide, akarizide und ovizide Wirksamkeit.

  通式(I)的新取代哒嗪酮、 提供、 其中 R¹代表烷基、卤代烷基、烷氧基烷基、烷硫基烷基、（二）烷基氨基烷基、烯基、卤代烯基，在每种情况下均代表任选取代的环烷基、环烷基烷基、芳基或芳烷基、 R² 代表卤素或烷基、 R³ 和 R⁴ 各自代表氢或烷基、 R⁵ 和 R⁶ 分别代表氢、羧基、任选取代的直链或支链烷基、烯基、烷氧羰基、芳基、芳烷基，或与它们所键合的碳原子一起代表任选取代的饱和或不饱和碳环、 R⁷、R⁸、R⁹、R¹⁰ 和 R¹ 各自代表氢、卤素、烷基、卤代烷基、烷氧基、卤代烷氧基、烷硫基或卤代烷硫基，以及 X代表氧或硫。 式（I）的新化合物对害虫具有非常明显的活性，尤其是良好的杀虫、杀螨虫和杀卵活性。
• Synthesis and Structure−Phytotoxicity Relationships of Acetylenic Phenols and Chromene Metabolites, and Their Analogues, from the Grapevine Pathogen <i>Eutypa </i><i>l</i><i>ata</i>
  作者：Leverett R. Smith、Noreen Mahoney、Russell J. Molyneux

  DOI：10.1021/np020415t

  日期：2003.2.1

  Eutypa lata, the fungus responsible for dying-arm disease in grapevines, produces a number of structurally related secondary metabolites, of which eutypine (1) has been implicated as the principal phytotoxin. However, analysis of an E. lata strain from California known to be pathogenic to grapevines showed that eutypine was not present, suggesting that other metabolites could be phytotoxic. Investigation of the relative phytotoxicities of individual metabolites has been limited by insufficient material and lack of a reliable bioassay. Metabolites of particular interest and their precursors were therefore synthesized, and a rapid, quantitative bioassay via topical application of individual compounds to disks of grape leaves and measurement of chlorophyll loss was developed to provide a relative measure of tissue damage. The recently reported metabolite eulatachromene (2) was found to have phytotoxicity greater than that of eutypine (1). The cyclization product, 5-formyl-2-methylvinyl[1]benzofuran (3), also showed significant activity, whereas the reduction product, eutypinol (4), was inactive, as was the quinol, siccayne (5). These results indicate that before strains of Eutypa are incriminated as pathogenic they must be analyzed for the presence or absence of specific constituents for which the phytotoxicity has been unequivocally established.
• New Class of Algicidal Compounds and Fungicidal Activities Derived from a Chromene Amide of Amyris texana
  作者：Kumudini M. Meepagala、Kevin K. Schrader、Charles L. Burandt、David E. Wedge、Stephen O. Duke

  DOI：10.1021/jf101626g

  日期：2010.9.8

  A chromene amide, N-[2-(2,2-dimethyl-2H-1-benzopyran-6-yl)ethyl]-N,3-dimethylbutanamide, was isolated from the EtOAc extract of the leaves of Amyris texana and found to have moderate antifungal activity against Colletotrichum spp. and selective algicidal activity against Planktothrix perornata, a cyanobacterium (blue-green alga) that causes musty off-flavor in farm-raised channel catfish (Ictalurus punctatus). To improve the selective algicidal activity and provide water solubility, a series of chromene analogues were synthesized and evaluated for algicidal activity using a 96-well microplate rapid bioassay. In addition, the chromene analogues were evaluated for antifungal and phytotoxic activities. Hydrochloride salts of a chromene amine analogue showed improved water solubility and selectivity toward P. perornata with activity comparable to that of the naturally occurring chromene amide.