4-hydroxy-5,5-dimethyl-2(3H)-dihydrofuranone | 133220-72-1

• 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-hydroxy-5,5-dimethyl-2(3H)-dihydrofuranone
• 英文别名: 3-Hydroxy-4,4-dimethyl-gamma-butyrolactone；4-hydroxy-5,5-dimethyloxolan-2-one
• CAS: 133220-72-1
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: SIEVQTNTRMBCHO-UHFFFAOYSA-N

物化性质

• 熔点：
  148-149 °C(Solv: water (7732-18-5))
• 沸点：
  118-120 °C(Press: 1 Torr)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5,5-dimethyl-2(3H)-dihydrofuranone 生成 5,5-二甲基-2(5H)-呋喃酮
  参考文献：
  名称：

  BRIMA, THOMAS S.

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(oxiran-2-yl)propan-2-ol 在 sodium hydroxide 、 oxonium 作用下， 以 甲苯 为溶剂， 生成 4-hydroxy-5,5-dimethyl-2(3H)-dihydrofuranone
  参考文献：
  名称：

  Ring-opening of epoxyalcohols by diethylaluminium cyanide. Regio- and stereoselective synthesis of 1-cyano-2,3-diols

  摘要：

  Diethylaluminium cyanide is a highly selective reagent for the ring opening of 2,3-epoxyalcohols under mild conditions; the reaction takes place at C-3, with inversion of configuration, to give 1-cyano-2,3-diols. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02520-9

文献信息

• Decarboxylation of Paraconic Acids by a Silver(I) Nitrate/Persulfate Combination: An Entry to β-Nitro- and β-Hydroxy γ-Butyrolactones
  作者：Darunee Soorukram、Supasorn Phae-nok、Chutima Kuhakarn、Pawaret Leowanawat、Vichai Reutrakul

  DOI：10.1055/a-1792-7169

  日期：2022.9

  Decarboxylative transformations of paraconic acids, a class of γ-butyrolactones containing a carboxylic acid group at the β-position as their characteristic functionality, by using a combination of AgNO3/K2S2O8 were investigated. The dual function of AgNO3 as an initiator of the decarboxylation process and as a source of nitrogen dioxide radicals that react with aliphatic carboxylic substrates is reported

  通过使用AgNO 3 /K 2 S 2 O 8的组合，研究了对康酸（一类在β-位含有羧酸基团作为其特征官能团的γ-丁内酯）的脱羧转化。AgNO 3的双重功能作为脱羧过程的引发剂和作为与脂肪族羧酸底物反应的二氧化氮自由基的来源首次被报道。从仲康酸开始，在一锅操作中以中等的选择性获得了良好的综合收率 (41-85%) 的 β-硝基和 β-羟基 γ-丁内酯。在γ-丁内酯核可耐受的温和条件下，反应在可接受的反应时间（两小时）内完成。本研究提供了对 β-硝基和 β-羟基 γ-丁内酯的直接和位点特异性入口，它们是有机转化中的重要前体。
• Polymeric compound and resin composition for photoresist
  申请人：——

  公开号：US20020169266A1

  公开（公告）日：2002-11-14

  A photoresist polymeric compound includes a monomer unit represented by following Formula (I): 1 The polymeric compound may further include at least one of monomer units represented by following Formulae (IIa) to 2 wherein R 1 , R 13 , R 14 and R 15 are each a hydrogen atom or methyl group; R 2 and R 3 are each a hydrocarbon group having from 1 to 8 carbon atoms; R 4 , R 5 and R 6 are each a hydrogen atom, hydroxyl group or a methyl group; R 7 and R 8 are each a hydrogen atom, hydroxyl group or —COOR 9 group, where R 9 is a t-butyl group, 2-tetrahydropyranyl group, etc.; R 10 and R 11 are each a hydrogen atom, hydroxyl group or oxo group; R 12 is a hydrocarbon group having a tertiary carbon atom at a bonding site with an oxygen atom indicated in the formula; R 16 is a t-butyl group, 2-tetrahydropyranyl group, etc.; and n denotes an integer from 1 to 3. The photoresist polymeric compound can exhibit high adhesion to substrates and can highly precisely form fine patterns.

  一种光阻聚合物化合物包括以下式(I)所表示的单体单元：1该聚合物化合物还可以包括以下式(IIa)至(IIb)所表示的至少一种单体单元中的至少一种：其中，R1、R13、R14和R15均为氢原子或甲基基团；R2和R3均为具有1至8个碳原子的碳氢基团；R4、R5和R6均为氢原子、羟基或甲基基团；R7和R8均为氢原子、羟基或-COOR9基团，其中R9为叔丁基基团、2-四氢呋喃基团等；R10和R11均为氢原子、羟基或酮基；R12为具有在公式中指示的氧原子与三级碳原子成键位的碳氢基团；R16为叔丁基基团、2-四氢呋喃基团等；n表示1至3的整数。该光阻聚合物化合物可以表现出对基材的高粘附性，并可以高精度地形成细小图案。
• POLYMERIC COMPOUND FOR PHOTORESIST AND RESIN COMPOSITION FOR PHOTORESIST
  申请人：Daicel Chemical Industries, Ltd.

  公开号：EP1172694A1

  公开（公告）日：2002-01-16

  A photoresist polymeric compound includes a monomer unit represented by following Formula (I) : The polymeric compound may further include at least one of monomer units represented by following Formulae (IIa) to (IIg): wherein R1, R13, R14 and R15 are each a hydrogen atom or methyl group; R2 and R3 are each a hydrocarbon group having from 1 to 8 carbon atoms; R4, R5 and R6 are each a hydrogen atom, hydroxyl group or a methyl group; R7 and R8 are each a hydrogen atom, hydroxyl group or -COOR9 group, where R9 is a t-butyl group, 2-tetrahydropyranyl group, etc.; R10 and R11 are each a hydrogen atom, hydroxyl group or oxo group; R12 is a hydrocarbon group having a tertiary carbon atom at a bonding site with an oxygen atom indicated in the formula; R16 is a t-butyl group, 2-tetrahydropyranyl group, etc.; and n denotes an integer from 1 to 3. The photoresist polymeric compound can exhibit high adhesion to substrates and can highly precisely form fine patterns.

  一种光致抗蚀剂聚合化合物包括下式（I）所代表的单体单元： 该聚合化合物还可进一步包括下式（IIa）至（IIg）所代表的单体单元中的至少一种： 其中 R1、R13、R14 和 R15 各为氢原子或甲基；R2 和 R3 各为具有 1 至 8 个碳原子的烃基；R4、R5 和 R6 各为氢原子、羟基或甲基；R7 和 R8 各为氢原子、羟基或-COOR9 基，其中 R9 为叔丁基、2-四氢吡喃基等。R10 和 R11 分别是氢原子、羟基或氧代基团；R12 是烃基，其上的三级碳原子与式中所示的氧原子成键；R16 是叔丁基、2-四氢吡喃基等；n 表示 1 至 3 的整数。 这种光致抗蚀剂聚合物化合物对基底有很高的附着力，并能高度精确地形成精细图案。
• POLYMER FOR PHOTORESISTS AND RESIN COMPOSITIONS FOR PHOTORESISTS
  申请人：Daicel Chemical Industries, Ltd.

  公开号：EP1172384A1

  公开（公告）日：2002-01-16

  A polymeric compound of the invention includes at least one monomer unit selected from the following formulae (I), (II), (III) and (IV): (wherein R1 is a hydrogen atom or a methyl group, R2 and R3 are each a hydrogen atom, a hydroxyl group or a -COOR4 group, where R4 is, e.g., a t-butyl group or a 2-tetrahydropyranyl group; R5 and R6 are each a hydrogen atom, a hydroxyl group or an oxo group; R7, R8 and R9 are each a hydrogen atom or a methyl group; R10 and R11 are each a hydrocarbon group having 1 to 8 carbon atoms; R12, R13 and R14 are each a hydrogen atom, a hydroxyl group or a methyl group, where if all of R12 to R14 are each a hydrogen atom or a hydroxyl group, R10 and R11 are not coincidentally methyl groups) [wherein, when the compound includes, for example, a monomer unit of Formula (III), the compound further includes at least one monomer unit selected from among, for example, a monomer unit represented by the following Formula (V): (wherein R15 and R16 are each a hydrogen atom, a hydroxyl group or a carboxyl group; R17 is a hydroxyl group, an oxo group or a carboxyl group; and R1 has the same meaning as defined above)]. This polymeric compound has high etching resistance, as well as satisfactory transparency, alkali-solubility and adhesion, and is therefore useful as a photoresist resin.

  本发明的聚合化合物包括至少一种选自下式 (I)、(II)、(III) 和 (IV) 的单体单元： (其中 R1 为氢原子或甲基，R2 和 R3 各为氢原子、羟基或-COOR4 基团，其中 R4 例如为R5和R6各自为氢原子、羟基或氧代基团；R7、R8和R9各自为氢原子或甲基；R10和R11各自为具有1至8个碳原子的烃基；R12、R13 和 R14 各为氢原子、羟基或甲基，其中如果所有 R12 至 R14 各为氢原子或羟基，则 R10 和 R11 不同时为甲基）[其中，当该化合物包括例如式（III）的单体单元时，该化合物进一步包括至少一个选自例如下式（V）所代表的单体单元的单体单元： (其中 R15 和 R16 各为氢原子、羟基或羧基；R17 为羟基、氧代基团或羧基；R1 的含义与上述定义相同）]。这种聚合化合物具有很高的抗蚀刻性，以及令人满意的透明度、碱溶解性和粘附性，因此可用作光阻树脂。
• Formation of 3-acyloxy-γ-butyrolactones from 4-pentenols in vanadium-catalyzed oxidations
  作者：Matthias Amberg、Maike Dönges、Georg Stapf、Jens Hartung

  DOI：10.1016/j.tet.2014.05.011

  日期：2014.8

  O-Acyl derivatives of 3-hydroxy-gamma-butyrolactone are formed in up to 20% yield as by-products from 1-alkyl- and 1-phenyl-substituted 4-pentenols and tert-butyl hydroperoxide (TBHP) in vanadium-catalyzed synthesis of (tetrahydrofuran-2-yl)-methanols. The lactones are secondary products formed from (tetrahydrofuran-2-yl)-methanols via hydrogen atom abstraction in positions 4 and 5, as derived from experiments starting from deuterium-labeled alkenols. Stereocenters at tetrahydrofuran carbon 2 and the proximate hydroxyl carbon of the alkanol side chain retain configuration in the course of oxidative tetrahydrofuran conversion. In an atmosphere of nitrogen or argon, no gamma-butyrolactone formation occurs, pointing to dioxygen as terminal oxidant for the secondary oxidation. Adding cyclohexa-1,4-diene or gamma-terpinene to a solution of a 4-pentenol, TBHP, and a vanadium catalyst exposed to air inhibits formation of gamma-butyrolactones. A third approach to prevent gamma-butyrolactones from being formed in oxidative 4-pentenol cyclization uses cis-2,6-bis-(methanol)-piperidine instead of N-salicylidene-ortho-aminophenol as tridentate auxiliary for the vanadium catalyst. (C) 2014 Elsevier Ltd. All rights reserved.

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