4,4-Dimethyl-3-methylene-1-oxetan-2-one | 136066-39-2

• 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: 4,4-Dimethyl-3-methylene-1-oxetan-2-one
• 英文别名: 1-methyl-2-butyn-1-ol；4,4-Dimethyl-3-methylideneoxetan-2-one
• CAS: 136066-39-2
• 化学式: C₆H₈O₂
• 分子量: 112.128
• InChiKey: JRCXMUNSIYQDTA-UHFFFAOYSA-N

物化性质

• 沸点：
  194.6±9.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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：

  4-methylene-5,5-dimethyl-1,2-dioxolan-3-one 在 三苯基膦 作用下， 以 氯仿 为溶剂， 生成 4,4-Dimethyl-3-methylene-1-oxetan-2-one
  参考文献：
  名称：

  Synthesis of .alpha.-methylene .beta.-lactones, novel heterocycles

  摘要：

  Triphenylphosphine deoxygenation of beta-alkyl, beta,beta-dialkyl-, and beta,beta-spirocycloalkyl-substituted alpha-methylene-beta-peroxy lactones 3a-k, which are readily available by photooxygenation of the corresponding alpha,beta-unsaturated carboxylic acids 1, and cyclization of the resulting alpha-methylene-beta-hydroperoxy acids 2 constitute a convenient method for the preparation of a variety of alpha-methylene beta-lactones 5. Alternatively, the alpha-methylene-beta-hydroxy carboxylic acids 4 can be directly cyclized by benzenesulfonyl chloride in pyridine into these novel four-membered ring heterocycles 5.

  DOI：

  10.1021/jo00020a016

文献信息

• Ligand‐Controlled Palladium‐Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of α‐Methylene‐β‐Lactones
  作者：Yao Ge、Fei Ye、Jiawang Liu、Ji Yang、Anke Spannenberg、Haijun Jiao、Ralf Jackstell、Matthias Beller

  DOI：10.1002/anie.202006550

  日期：2020.11.23

  The first general and regioselective Pd‐catalyzed cyclocarbonylation to give α‐methylene‐β‐lactones is reported. Key to the success for this process is the use of a specific sterically demanding phosphine ligand based on N‐arylated imidazole (L11) in the presence of Pd(MeCN)2Cl2 as pre‐catalyst. A variety of easily available alkynols provide under additive‐free conditions the corresponding α‐methylene‐β‐lactones

  报道了第一个普通的和区域选择性的Pd催化的环羰基化反应，生成α-亚甲基-β-内酯。该工艺成功的关键是在Pd（MeCN）2 Cl 2作为预催化剂的情况下，使用基于N-芳基化咪唑（L11）的特定空间要求的膦配体。在无添加剂条件下，各种容易获得的炔醇以中等至良好的产率提供相应的α-亚甲基-β-内酯，具有出色的区域选择性和非对映选择性。这种新方法的适用性通过包括天然产物在内的生物活性分子的直接羰基化得以展示。
• Carbonylation of alkynols catalyzed by Pd(II)/2-PyPPh 2 dissolved in organic solvents and in ionic liquids: a facile entry to α-methylene γ- and δ-lactones
  作者：Crestina S Consorti、Gunter Ebeling、Jaı̈rton Dupont

  DOI：10.1016/s0040-4039(01)02309-7

  日期：2002.1

  The carbonylation of terminal 3-alkyn-1-ols and 1-alkyn-4-ols by Pd(OAc)(2) associated with 2-(diphenylphosphino)pyridine (2-PyPPh2) dissolved in organic solvents or in 1-n-butyl-3-methyl imidazolium ionic liquids affords quantitatively and selectively exo-alpha-methylene gamma- and delta-lactones, respectively. In the case of the reactions performed in ionic liquids (biphasic conditions), the lactones were isolated by simple distillation and the ionic catalyst solution can be reused. (C) 2002 Elsevier Science Ltd. All rights reserved.
• POLYMER AND CHEMICALLY AMPLIFIED RESIST COMPOSITION COMPRISING THE SAME
  申请人：FUJI Yusuke

  公开号：US20090264565A1

  公开（公告）日：2009-10-22

  The present invention provides a polymer comprising a structural unit represented by the formula (Ia) or (Ib): wherein R 1 represents a hydrogen atom etc., R 2 represents a linear, branched chain or cyclic C1-C8 alkyl group, R 3 represents a methyl group, n represents an integer of 0 to 14, Z 1 represents a single bond etc., k represents an integer of 1 to 4, R 4 and R 5 each independently represents a hydrogen atom etc., and m represents an integer of 1 to 3, a structural unit represented by the formula (II): wherein R 6 and R 7 each independently represents a hydrogen atom etc., R 8 represents a methyl group, R 9 represents a hydrogen atom etc., Z 2 represents a single bond etc., k′ represents an integer of 1 to 4, Z′ represents a group capable to eliminate by an action of an acid, and a structural unit represented by the formula (III): wherein R 10 represents a carboxyl group etc., l′ represents an integer of 0 to 3, Z 3 represents a single bond etc., and k″ represents an integer of 1 to 4.
• US7981985B2
  申请人：——

  公开号：US7981985B2

  公开（公告）日：2011-07-19
• US8048612B2
  申请人：——

  公开号：US8048612B2

  公开（公告）日：2011-11-01