4-Methylene-2H-pyran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-Methylene-2H-pyran-2-one
• 英文别名: 4-Methylideneoxan-2-one
• 化学式: C₆H₈O₂
• 分子量: 112.128
• InChiKey: AQABCRMCIOTZMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(tert-Butyldimethylsiloxy)-2-oxa-5-methylbicyclo<3.1.0>hexane 在 magnesium(II) perchlorate 、 对氰基苯乙酮 、 水 作用下， 以 乙腈 为溶剂， 以28%的产率得到4-甲基-5,6-二氢吡喃-2-酮
  参考文献：
  名称：

  Oxidative Ring-Opening Reaction of Cyclopropanone Acetals with Carbonyl Compounds via Photoinduced Electron Transfer. Generation of a .beta.-Carbonyl Radical Species and Its Application to the Synthesis of .gamma.-Hydroxy Ester Derivatives

  摘要：

  Photoinduced electron transfer (PET) reactions of 2-substituted or 2,2-disubstituted cyclopropanone methyl trialkylsilyl acetals 1a-e,g and 1-siloxy-2-oxabicyclo[3.1.0]hexane (1f) with carbonyl compounds 2 (benzophenone (2a), acetophenone (2b), 2-acetonaphthone (2c), 2-acetylpyridine (2d), 4-acetylbenzonitrile (2e), 2,3-butanedione (2f), and benzoyl cyanide (2g)) were examined in the presence of Mg(ClO4)(2). Carbon-carbon bond coupling products (gamma-hydroxy esters 3 or their derivative butyrolactones 4) between 1 and 2 were formed in good yields. A mechanism is proposed for the product formation which is initiated by the single electron transfer (SET) from 1 to the excited state of 2. The SET generates a transient pair of ion radicals, i.e. a ring-opened sec- or tert-beta-carbonyl radical from 1 and a ketyl radical ion from 2 stabilized by the Mg salt. This realizes a novel type of carbon-carbon bond formation at the sterically crowded beta-position of propanoates.

  DOI：

  10.1021/jo00115a022

文献信息

• PROCESSES FOR CONVERSION OF BIOLOGICALLY DERIVED MEVALONIC ACID
  申请人：Visolis, Inc.

  公开号：US20160145227A1

  公开（公告）日：2016-05-26

  The invention relates to a process comprising reacting mevalonic acid, or a solution comprising mevalonic acid, to yield a first product or first product mixture, optionally in the presence of a solid catalyst and/or at elevated temperature and/or pressure. The invention further relates to a process comprising: (a) providing a microbial organism that expresses a biosynthetic mevalonic acid pathway; (b) growing the microbial organism in fermentation medium comprising suitable carbon substrates, whereby biobased mevalonic acid is produced; and (c) reacting said biobased mevalonic acid to yield a first product or first product mixture.

  这项发明涉及一种过程，包括将甲烷酸或含有甲烷酸的溶液反应，以产生第一产品或第一产品混合物，可选地在固体催化剂的存在下和/或在升高的温度和/或压力下。该发明还涉及一种过程，包括：(a)提供表达生物合成甲烷酸途径的微生物生物体；(b)在包含适当碳基底物的发酵培养基中培养微生物生物体，从而产生生物基甲烷酸；以及(c)将所述生物基甲烷酸反应，以产生第一产品或第一产品混合物。
• [EN] POLYMERS PREPARED FROM MEVALONOLACTONE AND DERIVATIVES<br/>[FR] POLYMÈRES PRÉPARÉS À PARTIR DE LA MÉVALONOLACTONE ET DE SES DÉRIVÉS
  申请人：VISOLIS INC

  公开号：WO2016077555A1

  公开（公告）日：2016-05-19

  Described herein polymer precursor compounds (aka polymer building blocks) of derived from biobased compounds, and specifically biobased mevalonolactone and its related derivatives. Through oxidation these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols and polyamides, as well as precursors for glycidyl esters and omega-alkenyl esters. Through reduction, these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols, polycarbonates, as well as precursors for glycidyl ethers and omega-alkenyl ethers. Through nucleophilic ring opening and/or amidation, these biobased precursors can be reacted to yield building blocks for polyester polyols, chain-extender for polyurethanes, or polyester-amides.

  本文描述了从生物基化合物中衍生的聚合物前体化合物（又称聚合物构建模块），特别是生物基美伐酮内酯及其相关衍生物。通过氧化，这些生物基前体可以被反应生成（不饱和的）聚酯、聚酯多元醇和聚酰胺的构建模块，以及环氧酯和ω-烯基酯的前体。通过还原，这些生物基前体可以被反应生成（不饱和的）聚酯、聚酯多元醇、聚碳酸酯的构建模块，以及环氧醚和ω-烯基醚的前体。通过亲核环开和/或酰胺化，这些生物基前体可以被反应生成聚酯多元醇的构建模块，聚氨酯的扩链剂，或聚酯酰胺。
• POLYMERS PREPARED FROM MEVALONOLACTONE AND DERIVATIVES
  申请人：Visolis, Inc.

  公开号：US20160130389A1

  公开（公告）日：2016-05-12

  Described herein polymer precursor compounds (aka polymer building blocks) of derived from biobased compounds, and specifically biobased mevalonolactone and its related derivatives. Through oxidation these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols and polyamides, as well as precursors for glycidyl esters and omega-alkenyl esters. Through reduction, these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols, polycarbonates, as well as precursors for glycidyl ethers and omega-alkenyl ethers. Through nucleophilic ring opening and/or amidation, these biobased precursors can be reacted to yield building blocks for polyester polyols, chain-extender for polyurethanes, or polyester-amides.

  本文描述了从生物基化合物中衍生出的聚合物前体化合物（又称聚合物构建块），特别是生物基美瓦酮内酯及其相关衍生物。通过氧化，这些生物基前体可以反应产生（不饱和）聚酯、聚酯多元醇和聚酰胺的构建块，以及环氧酯和ω-烯基酯的前体。通过还原，这些生物基前体可以反应产生（不饱和）聚酯、聚酯多元醇、聚碳酸酯的构建块，以及环氧醚和ω-烯基醚的前体。通过亲核环开和/或酰胺化，这些生物基前体可以反应产生聚酯多元醇、聚氨酯的链延长剂，或聚酯酰胺的构建块。
• Dérivés de pyrrolidines et de thiazolidines, leur procédé de préparation et les utilisation pour le traitement de l'hyperglycémie et du diabète de type II
  申请人：Les Laboratoires Servier

  公开号：EP1598350A1

  公开（公告）日：2005-11-23

  Composé de formule (I) : dans laquelle : X1 représente un atome ou groupement choisi parmi CR4aR4b, O, S(O)q1 et NR5, où R4a, R4b, q1 et R5, m1, m2, n1 et n2 sont tels que définis dans la description, Ak représente une chaîne alkylène éventuellement substituée, p représente zéro, 1 ou 2, R3 représente un atome d'hydrogène ou un groupement cyano, X2 et X3, identiques ou différents, représentent chacun, soit un groupement S(O)q2, soit un groupement CR6aR6b, où q2, R6a, R6b, R1 et R2 sont tels que définis dans la description, la préparation de ces composés et leur utilisation comme inhibiteurs de dipeptidyl-peptidase IV.

  式 (I) 的化合物 其中： X1 代表选自 CR4aR4b、O、S(O)q1 和 NR5 的原子或基团，其中 R4a、R4b、q1 和 R5、m1、m2、n1 和 n2 如说明中所定义、 Ak 代表任选取代的亚烷基链、 p 代表 0、1 或 2、 R3 代表氢原子或氰基、 X2 和 X3 可以相同或不同，各自代表 S(O)q2 基团或 CR6aR6b 基团，其中 q2、R6a、R6b、R1 和 R2 如说明中所定义、 这些化合物的制备及其作为二肽基肽酶 IV 抑制剂的用途。
• Processes for conversion of biologically derived mevalonic acid
  申请人：Visolis, Inc.

  公开号：US10208008B2

  公开（公告）日：2019-02-19

  A process is provided for converting mevalonic acid into various useful products and derivatives. More particularly, the process comprises reacting mevalonic acid, or a solution comprising mevalonic acid, in the presence of a solid catalyst at an elevated temperature and pressure to thereby form various biobased products. The process may also comprise: (a) providing a microbial organism that expresses a biosynthetic mevalonic acid pathway; (b) growing the microbial organism in fermentation medium comprising suitable carbon substrates, whereby biobased mevalonic acid is produced; and (c) reacting the biobased mevalonic acid in the presence of a solid catalyst at an elevated temperature and pressure to yield various biobased products.

  提供了一种将甲羟戊酸转化为各种有用产品和衍生物的工艺。更具体地说，该工艺包括在固体催化剂存在下，在高温高压下使甲羟戊酸或包含甲羟戊酸的溶液发生反应，从而形成各种生物基产品。该工艺还可包括：(a) 提供表达生物合成甲羟戊酸途径的微生物有机体；(b) 在包含适当碳底物的发酵培养基中培养微生物有机体，从而产生生物基甲羟戊酸；(c) 在固体催化剂存在下，在高温高压下反应生物基甲羟戊酸，生成各种生物基产品。