3,4-dihydro-6-methyl-2H-1-benzopyran-3-ol | 37815-97-7

• 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: 3,4-dihydro-6-methyl-2H-1-benzopyran-3-ol
• 英文别名: 6-Methyl-3-chromanol；6-methyl-chroman-3-ol；6-methyl-3,4-dihydro-2H-chromen-3-ol
• CAS: 37815-97-7
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: LKJOFWMZYHCRAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-[(2-溴-4-甲基苯氧基)甲基]环氧乙烷 生成 3,4-dihydro-6-methyl-2H-1-benzopyran-3-ol
  参考文献：
  名称：

  BRADSHER C. K.; REAMES D. C., J. ORG. CHEM., 1978, 43, NO 19, 3800-3802

  摘要：

  DOI：

文献信息

• [EN] HETEROBICYCLE-SUBSTITUTED AZOLYL BENZENE FUNGICIDES<br/>[FR] FONGICIDES D'AZOLYL BENZÈNE SUBSTITUÉ PAR HÉTÉROBICYCLE
  申请人：DU PONT

  公开号：WO2011059619A1

  公开（公告）日：2011-05-19

  Disclosed are compounds of Formula 1, including all stereoisomers, N oxides, and salts thereof, wherein Y is a 5-membered, fully or partially unsaturated heterocyclic ring containing 2-4 carbon atoms and 2-3 nitrogen atoms as ring members, the ring substituted with Z on a ring member atom connected through an adjacent single ring member atom to the ring member atom attaching the heterocyclic ring to the phenyl ring of Formula 1, and optionally further substituted with up to 2 substituents independently selected from R5 on carbon atom ring members and from R6 on nitrogen atom ring members; Z is an 8-, 9-, 10- or 11-membered fused heterobicyclic ring system containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are independently selected from S(=O)u(=NR7)z, the ring system optionally substituted with substituents independently selected from R8 on carbon atom ring members and from R9 on nitrogen atom ring members; and R1, R2, R3, R4, R5, R6, R7, R8, R9, u and z are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.

  公开的是Formula 1的化合物，包括所有立体异构体、N-氧化物和盐，其中Y是一个5元的、完全或部分不饱和的杂环环，含有2-4个碳原子和2-3个氮原子作为环成员，该环在通过相邻的单环成员原子连接到将杂环环连接到Formula 1的苯环上的环成员原子上与Z取代，并且可选地进一步取代最多2个取代基，独立地从碳原子环成员上的R5和氮原子环成员上的R6中选择；Z是一个8、9、10或11元的融合杂双环环系统，其中环成员从碳原子和1到4个异原子中独立选择，这些异原子最多选择2个O、最多2个S和最多4个N原子，其中最多3个碳原子环成员独立选择自C(=O)和C(=S)，硫原子环成员独立选择自S(=O)u(=NR7)z，环系统可选地取代取代基，独立地从碳原子环成员上的R8和氮原子环成员上的R9中选择；以及R1、R2、R3、R4、R5、R6、R7、R8、R9、u和z如披露中所定义。还公开了含有Formula 1的化合物的组合物以及用于控制由真菌病原体引起的植物病害的方法，包括施用本发明的化合物或组合物的有效量。
• A New and Facile Synthesis of Chroman-3-ols, 3,4-Dihydro-2H-[1]-Benzopyran-3-ols
  作者：V. Satyanarayana、Ch. Prasad Rao、G. L. David Krupadanam、G. Srimannarayana

  DOI：10.1080/00397919108016418

  日期：1991.7

  Abstract o-Allyl phenols react with m-chloroperoxybenzoic acid (m-CPBA) in dry chloroform to give chroman-3-ols in a single step in good yields (93–96%).

  摘要 邻烯丙基苯酚在无水氯仿中与间氯过氧苯甲酸 (m-CPBA) 反应，一步生成色满-3-醇，产率高（93-96%）。
• 一种合成苯并吡喃3醇衍生物类化合物的方法
  申请人：浙江工业大学

  公开号：CN111423405B

  公开（公告）日：2021-11-26

  本发明涉及化合物制备技术领域，公开了一种合成苯并吡喃3醇衍生物类化合物的方法，包括如下步骤：（1）将化合物I与钯催化剂、氧化剂和溶剂混合，在70~130℃下密闭搅拌反应1~24h；对步骤（1）所得混合液进行后处理得到中间产物II；将中间产物II与催化剂、乙腈和水混合，用氮气置换空气后，在85~95℃下密闭搅拌反应1~24h；对步骤（3）所得混合液进行后处理得到终产物III苯并吡喃3醇衍生物类化合物。本发明通过交叉脱氢偶联直接进行分子内C(sp3)‑H芳基化，合成苯并吡喃3醇衍生物类化合物，路线简单，收率较高，普适性好，反应条件温和，选择性高。
• HETEROBICYCLE-SUBSTITUTED AZOLYL BENZENE FUNGICIDES
  申请人：Andreassi II John Lawrence

  公开号：US20120202815A1

  公开（公告）日：2012-08-09

  Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, wherein Y is a 5-membered, fully or partially unsaturated heterocyclic ring containing 2-4 carbon atoms and 2-3 nitrogen atoms as ring members, the ring substituted with Z on a ring member atom connected through an adjacent single ring member atom to the ring member atom attaching the heterocyclic ring to the phenyl ring of Formula 1, and optionally further substituted with up to 2 substituents independently selected from R 5 on carbon atom ring members and from R 6 on nitrogen atom ring members; Z is an 8-, 9-, 10- or 11-membered fused heterobicyclic ring system containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2O, up to 2S and up to 4 N atoms, wherein up to 3 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O) u (═NR 7 ) z , the ring system optionally substituted with substituents independently selected from R 8 on carbon atom ring members and from R 9 on nitrogen atom ring members; and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , u and z are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.

  本文披露了一种公式1的化合物，包括所有立体异构体、N-氧化物和其盐。其中Y是一个五元杂环环，完全或部分不饱和，包含2-4个碳原子和2-3个氮原子作为环成员，环上通过相邻的单个环成员原子连接到连接杂环环和公式1苯环的环成员原子上的Z进行取代。环还可以进一步取代最多2个取代基，独立地从碳原子环成员和氮原子环成员的R5和R6中选择。Z是一个8、9、10或11个成员的融合杂双环系统，其中环成员选择自碳原子和1至4个杂原子，独立地从最多2个O、最多2个S和最多4个N原子中选择，其中最多3个碳原子环成员独立地选择自C（═O）和C（═S），硫原子环成员独立地选择自S（═O）u（═NR7）z，环系统还可以进一步取代独立地从碳原子环成员的R8和氮原子环成员的R9中选择的取代基。R1、R2、R3、R4、R5、R6、R7、R8、R9、u和z如本文所定义。本文还披露了含有公式1化合物的组合物，并且披露了一种通过施用本发明的化合物或组合物的有效量来控制由真菌病原体引起的植物病害的方法。
• Preparation and chemistry of the active copper species derived from CuI.cntdot.PBu3, CuI.cntdot.PPh3, and CuCN.cntdot.nLiX complexes
  作者：Reuben D. Rieke、Douglas E. Stack、Bryan T. Dawson、Tse Chong Wu

  DOI：10.1021/jo00061a023

  日期：1993.4

  The preparation of highly reactive copper by the reduction of CuI.PBu3, CuI.PPh3, and CuCN-nLiX copper(I) complexes with the preformed lithium naphthalenide is described. It was found, for all three Cu(I) complexes, that the reduction temperature proved crucial to reactivity of the zerovalent copper species as measured by the ability of the active copper to undergo oxidative addition to carbon-halogen bonds. The lower the reduction temperature the more reactive the zerovalent copper species becomes. The low-temperature reduction allows for the formation of highly reactive copper from CuCN.nLiX complexes. This active copper species undergoes oxidative addition to alkyl and aryl bromides in high yield to form the corresponding organocopper reagent directly without the need for other organometallic precursors. Moreover, the alkyl and aryl bromides can contain a wide range of functional groups as they are not affected in the oxidative addition step. The functionalized organocopper reagents derived from CuCN-nLiX based active copper are the reagent of choice in the cross-coupling of acid chlorides to produce ketones as well as the 1,4-addition reaction with enones. The lack of phosphines associated with organocopper reagents stemming from CuCN-based active copper makes product isolation more facile. While the functionalized organocopper reagents derived from CuCN.nLiX complexes provide higher isolated yields in the formentioned reactions, they are not nucleophilic enough to undergo inter- or intramolecular epoxide openings. The use of both CuI.PBu3 and CuI.PPh3 Cu(I) complexes in the intramolecular epoxide openings of aryl bromoepoxides is presented. The regiochemistry, endo vs. exo, was shown to be affected by the Cu(I) complex used to generate the active copper species, the solvent, and the pattern of substitution around the epoxide moiety. The active copper species as well as the the resulting organocopper reagents derived from both CuI.PBu3 and CuCN-nLiX were investigated using both P-31 and C-13 NMR. The data from P-31 NMR investigation held some evidence for a highly reduced copper(0)-phosphine complex while the C-13 studies of the CuCN-nLiX complexes indicated that these species have limited solubility in THF.