5-(4-bromophenyl)-2,2-dimethyl-1,3-dioxolan-4-one | 42216-15-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-bromophenyl)-2,2-dimethyl-1,3-dioxolan-4-one
• CAS: 42216-15-9
• 化学式: C₁₁H₁₁BrO₃
• 分子量: 271.111
• InChiKey: POAXYEDTHRJFHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-bromophenyl)-2,2-dimethyl-1,3-dioxolan-4-one 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 2-(4-bromophenyl)pent-4-ene-1,2-diol
  参考文献：
  名称：

  Lipase AKG mediated resolutions of α,α-disubstituted 1,2-diols in organic solvents; remarkably high regio- and enantio-selectivity

  摘要：

  Diols 1, which contain adjacent tertiary and primary hydroxy groups, can be selectively mono-acylated at the primary hydroxy group by many lipases in organic solvents, Since the reaction does not take place at the chiral tertiary centre itself, observed enantioselectivities are usually low. Only the combination of one lipase, lipase AKG (Amano, Pseudomonas sp.), with selected substrates gives high enantioselectivities (E 20 to > 200), Also, the solvent and acyl donor employed influences the outcome, On the basis of the results of Lipase AKG towards substrates 1 an active site model for this specific lipase has been developed, which can account for the results obtained, Fu!! experimental details on the synthesis of diols 1 and enzymatic preparation of acetates 2 are given, Also, the absolute stereochemistry of the enzymatically prepared diols 1 has been established by independent synthesis from (R)-mandelic acid.

  DOI：

  10.1039/p19960002051
• 作为产物：
  描述：

  对溴扁桃酸 在 硫酸 、 丙酮 作用下， 生成 5-(4-bromophenyl)-2,2-dimethyl-1,3-dioxolan-4-one
  参考文献：
  名称：

  Reductive Cleavage of Dioxolones by the Grignard Reagent

  摘要：

  DOI：

  10.1021/ja01259a022
• 作为试剂：
  描述：

  对溴扁桃酸 、 硫酸 、 disodium;carbonate 、 丙酮 在 5-(4-bromophenyl)-2,2-dimethyl-1,3-dioxolan-4-one 、 ice 作用下， 以 水 为溶剂， 反应 0.5h， 生成 5-(4-bromophenyl)-2,2-dimethyl-1,3-dioxolan-4-one
  参考文献：
  名称：

  Phenyl-propargylether derivatives

  摘要：

  本发明涉及一般式I的苯基-丙炔醚衍生物，包括其光学异构体和混合物，其中R1为氢、烷基、环烷基或可选择取代的芳基，R2和R3各自独立地为氢或烷基，R4为烷基、烯基或炔基，R5、R6、R7和R8各自独立地为氢或烷基，R9为氢、可选择取代的烷基、可选择取代的烯基或可选择取代的炔基，R10为可选择取代的芳基或可选择取代的杂环芳基，Z为卤素、可选择取代的芳氧基、可选择取代的烷氧基、可选择取代的烯氧基、可选择取代的炔氧基、可选择取代的芳硫基、可选择取代的烷硫基、可选择取代的烯硫基、可选择取代的炔硫基、可选择取代的烷亚砜基、可选择取代的烯亚砜基、可选择取代的炔亚砜基、可选择取代的烷磺酰基、可选择取代的烯磺酰基或可选择取代的炔磺酰基。这些化合物具有有用的植物保护特性，并可优越地用于农业实践中，以控制或预防植物受植物病原微生物，特别是真菌的侵害。

  公开号：

  US06683211B1

文献信息

• Process for the preparation of alpha hydroxycarboxylic acid amides
  申请人：Zeller Martin

  公开号：US20050014950A1

  公开（公告）日：2005-01-20

  The invention concerns a novel process for the preparation of 2-phenyl-2-hydroxy-N-[2-(3-alkoxy-4-hydroxyphenyl)-ethyl]-acetamides of the formula (I), wherein R 1 is alkyl, R 2 and R 3 are each independently hydrogen or alkyl, and R 4 is optionally substituted aryl or optionally substituted heteroaryl, which process comprises reacting a 2-(3-alkoxy-4-hydroxyphenyl)-ethylamine of the formula (II), wherein R 1 R 2 and R 3 are as defined above with a α-hydoxycarboxylic acid ester of the formula (III) or a dioxolanone of the formula (III)a, wherein R 4 is as defined above, and R 5 , R 6 and R 7 independently of each other are lower alkyl. The compounds of formula (I) are important intermediates for a novel group of fungicides derived from mandelic acid amides.

  本发明涉及一种新型的制备2-苯基-2-羟基-N-[2-(3-烷氧基-4-羟基苯基)-乙基]-乙酰胺（式（I））的方法，其中R1为烷基，R2和R3各自独立地为氢或烷基，而R4为可选的取代芳基或可选的取代杂环芳基，该方法包括将式（II）的2-(3-烷氧基-4-羟基苯基)-乙胺与式（III）的α-羟基羧酸酯或式（III）a的二氧杂环戊酮反应，其中R1、R2和R3如上所定义，而R4如上所述，而R5、R6和R7各自独立地为低烷基。式（I）的化合物是从苦杏仁酸酰胺衍生的一类新型杀菌剂的重要中间体。
• Synthesis and Lipase-Catalyzed Resolution of 5-(Hydroxymethyl)-1,3-dioxolan-4-ones:  Masked Glycerol Analogs as Potential Building Blocks for Pharmaceuticals
  作者：Robert P. Hof、Richard M. Kellogg

  DOI：10.1021/jo952021v

  日期：1996.1.1

  (Hydroxymethyl)-1,3-dioxolan-4-ones from mandelic and lactic acids and 1,5,5-trimethyl-3-phenyloxazolidin-2-one from mandelamide were alpha-alkylated using benzyl chloromethyl ether. Reductive debenzylation of the products of alkylation unmasked the hydroxymethyl groups. The compounds obtained in this fashion were subsequently subjected to lipase-catalyzed resolution in organic media. Depending on the lipase and substrate employed, enantiomeric ratios up to E = 200 were observed. The obtained optically pure compounds can be considered as masked 2-substituted glycerol equivalents, which could be used for the preparation of tertiary (aryloxy)propanolamines, compounds having potential beta-blocking activity.
• NOVEL PHENYL-PROPARGYLETHER DERIVATIVES
  申请人：Syngenta Participations AG

  公开号：EP1282595B1

  公开（公告）日：2004-07-14
• PROCESS FOR THE PREPARATION OF ALPHA-HYDROXYCARBOXYLIC ACID AMIDES
  申请人：Syngenta Participations AG

  公开号：EP1444195B1

  公开（公告）日：2005-08-10
• AZABICYCLIC, AZATRICYCLIC AND AZASPIROCYCLIC DERIVATIVES OF AMINOCYCLOHEXANE AS NMDA, 5HT3, AND NEURONAL NICOTINIC RECEPTOR ANTAGONISTS
  申请人：Merz Pharma GmbH & Co. KGaA

  公开号：EP1485086A1

  公开（公告）日：2004-12-15