3,4-dihydroxy-2,2-dimethylchroman | 91970-66-0

• 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-dihydroxy-2,2-dimethylchroman
• 英文别名: 2,2-dimethyl-chroman-3,4-diol；2,2-Dimethyl-chromandiol-(3,4)；2,2-Dimethyl-3,4-dihydro-2H-1-benzopyran-3,4-diol；2,2-dimethyl-3,4-dihydrochromene-3,4-diol
• CAS: 91970-66-0
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: XPERSQUJKVIRHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dihydroxy-2,2-dimethylchroman 、 乙烯 在 十二羰基三锇 、 1-金刚烷甲酸 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 为溶剂， 140.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以94%的产率得到3-ethyl-3-hydroxy-2,2-dimethylchroman-4-one
  参考文献：
  名称：

  Transfer（0）通过转移加氢催化乙烯和α-烯烃与二醇，酮醇或羟基酯的CC偶联

  摘要：

  衍生自Os 3（CO）12和XPhos（2-二环己基膦基-2'，4'，6'-三异丙基联苯）的（0）络合物催化α-羟基酯1a - 1i，α-酮醇1j的C-C偶联- 1O，或1,2-二醇二氢- 1J - 1O与乙烯2A以形成乙基叔醇3A - 10-30。如1-辛烯2b与附近的双加氧反应物1a，1b，1i，1j，1k的偶联所示，1m，具有完全水平的支链区域选择性的高级α-烯烃被转化为加合物4a，4b，4i，4j，4k，4m。氧化水平无关的C-C耦合是通过的反应表现出1-辛烯2B与二醇二氢- 1K，α酮醇1K，和二酮脱氢- 1K。功能化的烯烃2c - 2f与扁桃酸乙酯1a反应生成加合物5a - 8a作为单一的区域异构体。包括氘标记研究在内的集体数据与涉及烯烃-二酮氧化偶合形成氧杂-Osmacyclopentane的催化机制相一致，该氧杂-Osmacyclopentpentane在通过仲醇反应物上的

  DOI：

  10.1021/acs.joc.6b01923
• 作为产物：
  描述：

  2,2,-二甲基-2H-苯并吡喃 在 3-甲基吡唑 、 双氧水 、 甲基三氧化铼(VII) 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到3,4-epoxy-2,2-dimethylchroman
  参考文献：
  名称：

  An effective procedure for the synthesis of acid-sensitive epoxides: Use of 1-methylimidazole as the additive on methyltrioxorhenium-catalyzed epoxidation of alkenes with hydrogen peroxide

  摘要：

  已发现一种有效的方法，通过使用1-甲基咪唑作为共添加剂，抑制在过氧化氢催化的烯烃环氧化反应中酸敏感环氧化物的开环和重排。这种将3-甲基吡唑和1-甲基咪唑联合用作添加剂的方法被证明是一种有效的程序，可以为MTO催化的环氧化反应提供优秀的酸敏感环氧化物产率。

  DOI：

  10.1039/b926575a

文献信息

• NOVEL USE OF SUBSTITUTED CHROMAN-6-OLS
  申请人：DSM IP ASSETS B.V.

  公开号：US20210030022A1

  公开（公告）日：2021-02-04

  The present invention is directed towards the use of substituted chroman-6-ols of formula (I) wherein R 1 and R 2 are independently from each other H or C 1-11 -alkyl or (CH 2 ) n —OH with n being an integer from 1 to 4, or R 1 and R 2 represent together a keto group, 10 A is CHR 3 or C(═O), and wherein R 3 , R 4 and R 6 are independently from each other H or C 1-4 -alkyl, and wherein R 5 is H or OH or C 1-4 -alkyl or C 1-4 -alkoxy, as antioxidants, especially in feed such as pet food and feed ingredients such as fish meal, insect meal and poultry meal, as well as PUFA-containing oil such as marine oil, microbial oil, fungal oil, algal oil and PUFA-containing plant oil. The present invention is further directed towards feed ingredients and feed for insects, aquatic and terrestrial animals comprising such substituted chroman-6-ols of formula (I).

  本发明涉及使用式(I)的取代基氧杂环己烯-6-醇，其中R1和R2分别独立地为H或C1-11-烷基或(CH2)n—OH，其中n为1至4的整数，或者R1和R2共同表示酮基，A为CHR3或C(═O)，其中R3、R4和R6分别独立地为H或C1-4-烷基，R5为H或OH或C1-4-烷基或C1-4-烷氧基，作为抗氧化剂，特别是在饲料中，如宠物食品和饲料成分，如鱼粉、昆虫粉和禽畜粉，以及富含PUFA的油，如海洋油、微生物油、真菌油、藻类油和富含PUFA的植物油。本发明还涉及含有式(I)的这种取代基氧杂环己烯-6-醇的饲料成分和用于昆虫、水生和陆生动物的饲料。
• [EN] PROCESS FOR THE MANUFACTURE OF CHROMAN-6-OLS WITH SHORT SIDE CHAINS<br/>[FR] PROCÉDÉ DE PRODUCTION DE CHROMAN-6-OLS À CHAÎNES LATÉRALES COURTES
  申请人：DSM IP ASSETS BV

  公开号：WO2019185900A1

  公开（公告）日：2019-10-03

  The present invention is directed to a process for the manufacture of a compound of formula (III), comprising the step of reacting a compound of formula (I) with a compound of formula (IIA), (IIB) or (IIC) in the presence of an acid catalyst and in a mixture of two solvents, wherein OR is OH, acetate, methanoate, propionate, butyrate or benzoate, A is CH2, R1 is C1-5-alkyl, R2 is either H or C1-2-alkyl, R4 is either H or C1-4-alkoxy or C1-4-alkyl, R3 and R5 are independently from each other either H or C1-4-alkyl, and the first of the two solvents is water, and the second of the two solvents is selected from aliphatic C5-8-hydrocarbons, cycloaliphatic C5-8-hydrocarbons, dialkyl ethers and methyl-substituted benzenes and any mixture thereof.

  本发明涉及一种制备III式化合物的方法，包括在两种溶剂的混合物中，在酸催化剂的存在下，将I式化合物与IIA、IIB或IIC式化合物反应，其中OR为OH、醋酸、甲酸、丙酸、丁酸或苯甲酸，A为CH2，R1为C1-5烷基，R2为H或C1-2烷基，R4为H、C1-4烷氧基或C1-4烷基，R3和R5各自独立地为H或C1-4烷基。两种溶剂中的第一种为水，第二种为选择自脂肪族C5-8烃、环脂族C5-8烃、二烷基醚和甲基取代苯及其任意混合物。
• PROCESS FOR THE MANUFACTURE OF CHROMAN-6-OLS WITH SHORT SIDE CHAINS
  申请人：DSM IP Assets B.V.

  公开号：EP3774756A1

  公开（公告）日：2021-02-17
• [EN] NOVEL USE OF SUBSTITUTED CHROMAN-6-OLS<br/>[FR] NOUVELLE UTILISATION DE CHROMAN-6-OLS SUBSTITUÉS
  申请人：DSM IP ASSETS BV

  公开号：WO2019185894A1

  公开（公告）日：2019-10-03

  The present invention is directed towards the use of substituted chroman-6- ols of formula (I) wherein R1 and R2 are independently from each other H or C1-11-alkyl or (CH2)n─OH with n being an integer from 1 to 4, or R1 and R2 represent together a keto group, 10 A is CHR3 or C(=O), and wherein R3, R4 and R6 are independently from each other H or C1-4-alkyl, and wherein R5 is H or OH or C1-4-alkyl or C1-4-alkoxy, as antioxidants, especially in feed such as pet food and feed ingredients such as fish meal, insect meal and poultry meal, as well as PUFA-containing oil such as marine oil, microbial oil, fungal oil, algal oil and PUFA-containing plant oil. The present invention is further directed towards feed ingredients and feed for insects, aquatic and terrestrial animals comprising such substituted chroman-6-ols of formula (I).
• An effective procedure for the synthesis of acid-sensitive epoxides: Use of 1-methylimidazole as the additive on methyltrioxorhenium-catalyzed epoxidation of alkenes with hydrogen peroxide
  作者：Shigekazu Yamazaki

  DOI：10.1039/b926575a

  日期：——

  An effective method for suppression of ring opening and rearrangement of acid-sensitive epoxides during methyltrioxorhenium(MTO)-catalyzed epoxidation of alkenes with H2O2 by using 1-methylimidazole as a co-additive has been found. The combined use of 3-methylpyrazole and 1-methylimidazole as the additives has been found to be an effective procedure that affords excellent yields of acid-sensitive epoxides for MTO-catalyzed epoxidation.

  已发现一种有效的方法，通过使用1-甲基咪唑作为共添加剂，抑制在过氧化氢催化的烯烃环氧化反应中酸敏感环氧化物的开环和重排。这种将3-甲基吡唑和1-甲基咪唑联合用作添加剂的方法被证明是一种有效的程序，可以为MTO催化的环氧化反应提供优秀的酸敏感环氧化物产率。