2-tert-butyl-6-methyl-1,3-dioxin-4-one | 119322-99-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 英文名称: 2-tert-butyl-6-methyl-1,3-dioxin-4-one
• 英文别名: 2-(1,1-Dimethylethyl)-6-methyl-4H-1,3-dioxin-4-one
• CAS: 119322-99-5
• 化学式: C₉H₁₄O₃
• mdl: MFCD24390383
• 分子量: 170.208
• InChiKey: HWPXDBBVCANLFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 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：

  2-tert-butyl-6-methyl-1,3-dioxin-4-one 生成 (R)-2-叔丁基-6-甲基-1,3-二噁英-4-酮
  参考文献：
  名称：

  SEEBACH, DIETER;MULLER, STEFAN G.;GYSEL, URS;ZIMMERMANN, JURG, HELV. CHIM. ACTA, 71,(1988) N 5, C. 1303-1318

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2,6-三甲基-4H-1,3-二英-4-酮 、 特戊醛 以 均三甲苯 为溶剂， 反应 1.0h， 以60%的产率得到2-tert-butyl-6-methyl-1,3-dioxin-4-one
  参考文献：
  名称：

  Enantioselective Synthesis of Spiro Ethers and Spiro Ketals via Photoaddition of Dihydro-4-pyrones to Chiral 1,3-Dioxin-4-ones

  摘要：

  A versatile and highly stereoselective synthesis of spiro ethers and spiro ketals is presented. The key step in the developed synthetic sequence is based on diastereoselective intramolecular photoaddition of dihydro-4-pyrones to chiral 1,3-dioxin-4-ones. Subsequent fragmentation of the produced four-membered ring provides spiro ether structures. The spiro ethers can be transformed to their corresponding spiro ketals, with retention of configuration at the spiro center, via Baeyer-Villager oxidation. The configuration of the spiro center is defined by the facial selectivity at the photocycloaddition step. Two examples of complete stereofacial selectivity were achieved. The unique and important application of the developed sequence was demonstrated in enantioselective synthesis of a less thermodynamically stable spiro ketal 43.

  DOI：

  10.1021/jo970816r

文献信息

• Asymmetric induction in cuprate and photoadditions to 2-t-butyl-2,6-dimethyl-1,3-dioxin-4-one. Absolute but opposite face selectivities
  作者：Gordon L. Lange、Michael G. Organ

  DOI：10.1016/s0040-4039(00)60309-x

  日期：1993.2

  Cuprate addition to 2-t-butyl-2,6-dimethyl-1,3-dioxin-4-one (3 results in exclusive attack from the top face (side opposite the t-butyl group) of the molecule while photoaddition of 3 with cyclohexene or the ethylene ketal of 2-cyclohexenone gives exclusively adducts formed by reaction on the bottom face of the substrate.

  向2,6-叔丁基-2,6-二甲基-1,3-二恶英-4-酮中添加铜酸盐（3导致分子顶面（与叔丁基相反的一侧）的排他性进攻，而3的光加成则与环己烯或2-环己烯酮的乙烯缩酮一起使用时，只能在底物的底面上反应生成加合物。
• SUBSTITUTED AMINO TRIAZOLES USEFUL AS ACIDIC MAMMALIAN CHITINASE INHIBITORS
  申请人：OncoArendi Therapeutics Sp z o.o.

  公开号：US20160176843A1

  公开（公告）日：2016-06-23

  Disclosed are amino triazole compounds substituted by a carboxylate functional group or an bioisosteric polar functional group. Compounds having the carboxylate moiety or carboxylate bioisostere inhibit acidic mammalian chitinase. Also provided are methods of using the compounds to treat asthma reactions caused by allergens.

  本发明涉及一种带有羧酸基团或生物等构极性功能基团的氨基三唑化合物。带有羧酸基团或羧酸生物等构体的化合物能够抑制酸性哺乳动物几丁质酶。同时，本发明还提供了使用这些化合物治疗由过敏原引起的哮喘反应的方法。
• Substituted dioxanones and dioxinones
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0244143A2

  公开（公告）日：1987-11-04

  Compounds of the formulae: wherein R¹, R², R³ and R⁴ have a wide range of values are described as useful intermediates in the preparation of pharmaceuticals, etc, in particular in the preparation of optically active β-hydroxy α-substituted carboxylic acids. Processes for their preparation are described.

  式中的化合物 其中 R¹、R²、R³ 和 R⁴ 的值范围很广，是制备药物等，特别是制备光学活性 β-羟基 α-取代羧酸的有用中间体。本文介绍了其制备工艺。
• Photoadditions and Dialkylcuprate Additions to 2-tert-Butyl-2,6-dimethyl-1,3-dioxin-4-one and Related Heterocycles. Experimental, Ab Initio Theoretical, and X-Ray Structural Studies of Facial Selectivity and Enone Pyramidalization
  作者：Michael G. Organ、Robert D. J. Froese、John D. Goddard、Nicholas J. Taylor、Gordon L. Lange

  DOI：10.1021/ja00087a018

  日期：1994.4

  Preparation and ground-state reactions of 1,3-dioxinone(1), alpha,beta-unsaturated delta-lactone 4, and dihydropyranone 5 are reported. These three substrates have identical alkyl substituents but differ in the number and placement of oxygen atoms in the heterocycle. Reaction of 1 or 4 with (n-Bu)(2)CuLi leads to exclusive addition on the top face (side opposite the tert-butyl group) of the substrate while addition to 5 gives a 50:50 mixture of diastereomers. Pyramidalizations of the enone portions of 1, 4, and 5 (along with 2-cyclohexenone) have been predicted using ab initio Hartree-Fock (HF) methods with a split-valence plus polarization basis set, 6-31G*, and with the inclusion of electron correlation by Moller-Plesset perturbation theory (MP2). These predictions have been compared with the results of X-ray crystal structure determinations on related heterocycles which were present in the Cambridge Crystallographic Database. Both theoretical methods indicate that the extent of pyramidalization decreases in the following order: 1,3-dioxinones > alpha,beta-unsaturated delta-lactones > dihydropyranones > 2-cyclohexenones. This trend suggests that the facial selectivity observed in the ground-state reactions of 1, 4, and 5 is related to the extent of pyramidalization in the enone portion of these substrates. Photoaddition reactions of 1 with various cycloalkenes are also reported. The exclusive or major product in these reactions results from attack on the bottom face of 1. Thus, substrate 1 allows exclusive entry of ground-state reactants on the top face, but excited-state reactions occur exclusively or primarily on the bottom face.
• ARGINASE INHIBITORS AND THEIR THERAPEUTIC APPLICATIONS
  申请人：ONCOARENDI THERAPEUTICS S.A.

  公开号：US20180009830A1

  公开（公告）日：2018-01-11

  The inventive compounds are small molecule therapeutics that are potent inhibitors of arginase 1 and arginase 2 activity. The inventions also provides pharmaceutical compositions and methods for using the inventive compounds for treating or preventing a disease or condition associated with arginase activity.