5-methylene-2-phenyl-1,3-dioxolan-4-one | 101822-11-1

• 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-methylene-2-phenyl-1,3-dioxolan-4-one
• 英文别名: 1,3-Dioxolan-4-one, 5-methylene-2-phenyl-；5-methylidene-2-phenyl-1,3-dioxolan-4-one
• CAS: 101822-11-1
• 化学式: C₁₀H₈O₃
• 分子量: 176.172
• InChiKey: FBGYODLWYLEBCM-UHFFFAOYSA-N

物化性质

• 熔点：
  33-34 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  90 °C(Press: 2.0 Torr)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-Bromomethyl-2-phenyl-1,3-dioxolan-4-on 在 4-甲氧基苯酚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以78%的产率得到5-methylene-2-phenyl-1,3-dioxolan-4-one
  参考文献：
  名称：

  Synthese und Polymerisation von 2-Aryl-5-methylen-1,3-dioxolan-4-onen und Arylbis(5-methylen-1,3-dioxolan-2-yl-4-on)en

  摘要：

  DOI：

  10.1002/prac.199533701102

文献信息

• 5-Methylene-1,3-dioxolan-4-one derivatives, process for their production, polymers of the derivatives, resist compositions, and pattern formation process
  申请人：——

  公开号：US20040248031A1

  公开（公告）日：2004-12-09

  The 5-methylene-1,3-dioxolan-4-one derivative of the present invention is represented by the formula (1) indicated below, and it is a novel monomer from which a homopolymer and a copolymer excellent in light transparency and heat stability are obtained. Moreover, the polymer obtained by (co)polymerizing a monomer composition comprising the derivative represented by the formula (1) indicated below is excellent in the resist performance such as sensitivity, resolution and dry etching resistance, and solubility in an organic solvent, also having little line edge roughness, and thus it is preferably used as a resin for a resist composition. 1 wherein R 1 represents a bridged cyclic hydrocarbon group containing 4 to 16 carbon atoms, or a linear or branched alkyl group containing 1 to 6 carbon atoms which has a bridged cyclic hydrocarbon group containing 4 to 16 carbon atoms as a substituent; R 2 represents a hydrogen atom, or a linear or branched alkyl group containing 1 to 6 carbon atoms; or R 1 and R 2 represent a bridged cyclic hydrocarbon group containing 4 to 16 carbon atoms together with the carbon atom to which they are bound, provided that the alkyl group and the bridged cyclic hydrocarbon group may have at least one substituent selected from a group consisting of a linear or branched alkyl group containing 1 to 6 carbon atoms which may be optionally substituted, a hydroxy group, a carboxy group, an acyl group containing 2 to 6 carbon atoms, an alkoxy group containing 1 to 6 carbon atoms, and a carboxy group esterified with an alcohol containing 1 to 6 carbon atoms.

  本发明的5-亚甲基-1,3-二氧杂环戊酮衍生物的化学式如下所示，是一种新型单体，可制备出具有优异光透明度和热稳定性的均聚物和共聚物。此外，通过聚合由下式表示的衍生物组成的单体混合物得到的聚合物具有优异的感光性、分辨率、干法蚀刻抗性和有机溶剂溶解性，同时具有较小的线边粗糙度，因此它可作为光刻胶组分的树脂。其中，R1代表含有4到16个碳原子的桥环烃基，或含有4到16个碳原子的桥环烃基作为取代基的线性或支链烷基，R2代表氢原子，或含有1到6个碳原子的线性或支链烷基，或R1和R2与它们所连接的碳原子一起代表含有4到16个碳原子的桥环烃基，前提是烷基和桥环烃基可以具有至少一个选自以下一组的取代基：含有1到6个碳原子的线性或支链烷基（可以选择性地被取代）、羟基、羧基、含有2到6个碳原子的酰基、含有1到6个碳原子的烷氧基和含有1到6个碳原子的醇酯化的羧基。
• Degradable polymers
  申请人：Matyjaszewski Krzysztof

  公开号：US20070155926A1

  公开（公告）日：2007-07-05

  Polymers comprising a polymer backbone comprising one or more degradable units are described. The polymer may additionally comprise two or more polymer segments comprising radically (co)polymerizable vinyl monomer units. The degradable units may be independently selected from, but not limited to, at least one of hydrodegradable, photodegradable and biodegradable units between the polymer segments and dispersed along the polymer backbone. The degradable units may be derived from one or more monomers comprising a heterocyclic ring that is capable of undergoing radical ring opening polymerization, a coupling agent, or from a polymerization initiator, radically polymerizable monomers, as well as other reactive sources. Embodiments of the degradable polymer of claim are capable of degrading by at least one of a hydrodegradation, photodegradation or biodegradation mechanisms to form at least one of telechelic oligomer and telechelic polymeric fragments of the polymer. The degradable polymer may be able to degrade into polymer fragments having a molecular weight distribution of less than 5, or in certain applications it may be preferable for embodiments of the polymer to be capable of forming polymer fragments having a molecular weight distribution of the polymer fragments less than 3.0 or even less than 2.5. Embodiments of the present invention also include methods of producing degradable polymers.

  本发明涉及一种聚合物，其聚合骨架包含一个或多个可降解单元。该聚合物可能还包括两个或更多聚合物片段，其中包括自由基（共）聚合性乙烯单体单元。可降解单元可以独立选择，但不限于，在聚合物片段之间和沿聚合物骨架分散的至少一种水解降解、光降解和生物降解单元。可降解单元可以来源于一个或多个单体，包括能够经历自由基开环聚合的杂环环、偶联剂或聚合引发剂、自由基聚合性单体以及其他反应源。该可降解聚合物的实施例能够通过至少一种水解降解、光降解或生物降解机制降解，形成聚合物的末端寡聚物和末端聚合物片段。该可降解聚合物可以降解成分子量分布小于5的聚合物片段，或在某些应用中，最好是实施例能够形成分子量分布小于3.0甚至小于2.5的聚合物片段。本发明的实施例还包括制备可降解聚合物的方法。
• 5-METHYLENE-1,3-DIOXOLAN-4-ONE DERIVATIVES, PROCESS FOR THEIR PRODUCTION, POLYMERS OF THE DERIVATIVES, RESIST COMPOSITIONS, AND PATTERN FORMATION PROCESS
  申请人：MITSUBISHI RAYON CO., LTD.

  公开号：EP1447403B1

  公开（公告）日：2016-02-03
• Controlled Radical Polymerization and Copolymerization of 5-Methylene-2-phenyl-1,3-dioxolan-4-one by ATRP
  作者：Quinn Smith、Jinyu Huang、Krzysztof Matyjaszewski、Yueh-Lin Loo

  DOI：10.1021/ma050393s

  日期：2005.6.1

  The polymerization and copolymerization of a cyclic acrylate, 5-methylene-2-phenyl-1,3dioxolan-4-one (MPDO), by conventional radical polymerization and atom transfer radical polymerization (ATRP), were determined to occur by 1,2-vinyl addition according to C-13 NMR spectroscopy. Copolymerization of MPDO with methyl methacrylate (MMA) or styrene (S) led to copolymers with a much higher MPDO content than originally in the feed, suggesting high reactivity due to its captodative structure. PMPDO-PS copolymers were stable to UV irradiation and basic environments, confirming that copolymerization of MPDO also proceeded by 1,2-vinyl addition rather than ring opening. DSC heating scans of PMPDO-PMMA copolymers show a single T-g that increases with increasing MPDO content.
• Synthesis of Degradable Poly(methyl methacrylate) via ATRP:  Atom Transfer Radical Ring-Opening Copolymerization of 5-Methylene-2-phenyl-1,3-dioxolan-4-one and Methyl Methacrylate
  作者：Im Sik Chung、Krzysztof Matyjaszewski

  DOI：10.1021/ma034029+

  日期：2003.5.1