4-methyl-1,3-dioxol-2-one | 4427-89-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 4-methyl-1,3-dioxol-2-one
• 英文别名: methylvinylene carbonate
• CAS: 4427-89-8
• 化学式: C₄H₄O₃
• 分子量: 100.074
• InChiKey: HXXOPVULXOEHTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-methyl-1,3-dioxol-2-one 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 以43%的产率得到4-hydroxymethyl-2-oxo-1,3-dioxol-4-ene
  参考文献：
  名称：

  Jung, Michael E.; Blum, Roberto B.; Gaede, Bruce J., Heterocycles, 1989, vol. 28, # 1, p. 93 - 97

  摘要：

  DOI：
• 作为产物：
  描述：

  碳酸丙烯酯 在 氯 作用下， 生成 4-methyl-1,3-dioxol-2-one
  参考文献：
  名称：

  Studies on prodrugs. II. Preparation and characterization of (5-substituted 2-Oxo-1,3-dioxolen-4-yl)methyl esters of ampicillin.

  摘要：

  (5-取代的2-氧基-1,3-二恶烷-4-基)甲酸酯被设计为一种新型的青霉素前药。这些酯类化合物的制备经过确认，在小鼠口服给药后能产生比青霉素三水合物本身更高的血药浓度。那些能显著提高青霉素血药浓度的化合物在体外血液中容易水解。青霉素（5-甲基-2-氧基-1,3-二恶烷-4-基）甲酸酯盐酸盐（KBT-1585）在小鼠中显示出最佳的口服吸收性。

  DOI：

  10.1248/cpb.32.2241

文献信息

• 1,3-Dioxolen-2-one derivatives and process for production thereof
  申请人：Kanebo Ltd.

  公开号：US04342693A1

  公开（公告）日：1982-08-03

  A 1,3-dioxolen-2-one derivative of the general formula ##STR1## wherein R.sub.1 represents a hydrogen atom, a methyl group, or an aryl group, R.sub.2 represents a hydrogen atom, or may be taken together with R.sub.1 to form a divalent carbon chain residue, and x represents a halogen atom. The above compounds can be prepared by reacting a compound of the general formula ##STR2## with a halogenating agent, and are useful as protective group-introducing reagents for introducing protective groups into reagents in various chemical reactions, or as modifiers for prodrug preparation in medicine.

  一种通式为##STR1##的1,3-二氧杂环戊二酮衍生物，其中R.sub.1代表氢原子、甲基基团或芳基，R.sub.2代表氢原子，或者可以与R.sub.1一起形成二价碳链残基，x代表卤原子。上述化合物可通过将通式为##STR2##的化合物与卤化试剂反应制备，并且可用作用于各种化学反应中引入保护基的试剂，或者用作医学中的前药制备修饰剂。
• Novel ampicillin esters and production thereof
  申请人：Kanebo Ltd.

  公开号：US04389408A1

  公开（公告）日：1983-06-21

  A novel Ampicillin ester of the general formula ##STR1## wherein R.sub.1 represents a hydrogen atom, a methyl group or an aryl group, and R.sub.2 represents a hydrogen atom or may be taken together with R.sub.1 to form a divalent carbon chain residue, or its acid addition salt. The novel Ampicillin ester or its acid addition salt is prepared by (1) reacting a corresponding 6-N-acylamino penicillanic acid (II) or its salt with a compound of the formula ##STR2## wherein R.sub.1 and R.sub.2 are as defined above, and X is a halogen atom, or reacting a compound of the formula ##STR3## wherein R.sub.1 and R.sub.2 are as defined above, or its acid addition salt with a corresponding carboxylic acid (VI) or its reactive derivative, (2) thereafter, if required, when the resulting compound has the protected amino group or the group convertible to an amino group, deprotecting the protected amino group or converting said convertible group to an amino group, and (3) if further required, converting the product to an acid addition salt. The present invention provides also an antibacterial agent comprising the novel Ampicillin ester and a method for the treatment of infectious disease.

  一种通式为##STR1##的新型氨苄青霉素酯，其中R.sub.1代表氢原子、甲基基团或芳基，R.sub.2代表氢原子或可能与R.sub.1一起形成双价碳链残基，或其酸加合盐。该新型氨苄青霉素酯或其酸加合盐是通过以下步骤制备的：(1)将相应的6-N-酰氨基青霉素酸（II）或其盐与通式##STR2##的化合物反应，其中R.sub.1和R.sub.2如上定义，X为卤原子；或将通式##STR3##的化合物，其中R.sub.1和R.sub.2如上定义，或其酸加合盐与相应的羧酸（VI）或其活性衍生物反应；(2)然后，如有必要，当所得化合物具有保护氨基或可转化为氨基的基团时，去保护氨基或将可转化基团转化为氨基；(3)如有进一步需要，将产物转化为酸加合盐。本发明还提供了一种包含该新型氨苄青霉素酯的抗菌剂和用于治疗传染病的方法。
• An Organocatalytic Route to <i>endo</i>‐Vinylene Carbonates from Carbon Dioxide‐Based <i>exo</i>‐Vinylene Carbonates
  作者：Chang Qiao、Philipp D. Engel、Levi A. Ziegenhagen、Frank Rominger、Ansgar Schäfer、Peter Deglmann、Peter Rudolf、Peter Comba、A. Stephen K. Hashmi、Thomas Schaub

  DOI：10.1002/adsc.202301374

  日期：2024.1.30

  An organocatalytic route has been developed for the isomerization of exo‐vinylene carbonates (exo‐VCs) to endo‐vinylene carbonates (endo‐VCs). The exo‐VC starting material can easily be obtained from propargylic alcohols via cyclization with carbon dioxide. In this study, these exo‐VCs are shown to isomerize to the thermodynamically more stable endo‐VCs in the presence of an N‐heterocyclic base and phenol. Density functional theory (DFT) studies were conducted to elucidate the mechanism, tackling difficulties of the description of charge separation steps. This isomerization process delivers an ample diversity of endo‐VCs in good to excellent yields and chemoselectivities under mild reaction conditions.

  摘要 开发了一种将外乙烯基碳酸酯（exo-VCs）异构化为内乙烯基碳酸酯（endo-VCs）的有机催化路线。外乙烯基碳酸酯起始原料可以很容易地从丙炔醇中通过与二氧化碳的环化反应获得。本研究表明，在 N-杂环碱和苯酚存在下，这些外-VC 会异构化成热力学上更稳定的内-VC。为了阐明其机理，我们进行了密度泛函理论（DFT）研究，以解决电荷分离步骤描述方面的难题。在温和的反应条件下，这一异构化过程产生了多种多样的内 VCs，产率和化学选择性都非常好。
• A Useful Synthetic Equivalent of a Hydroxyacetone Enolate
  作者：Miljan Bigovic、Veselin Maslak、Zorana Tokic-Vujosevic、Vladimir Divjakovic、Radomir N. Saicic

  DOI：10.1021/ol2019357

  日期：2011.9.2

  Indium promoted allyiation of carbonyl compounds with 4-(bromomethyl)-1,3-dioxol-2-one diastereoselectively affords and-alpha,beta-dihydroxyketones, protected as enol carbonates. These initial products can be deprotected to free dihydroxyketones or transformed under mild conditions Into the corresponding cyclic carbonates, which constitutes a useful approach to hydroxyacetone aldois.
• CN117247368
  申请人：——

  公开号：——

  公开（公告）日：——