(E)-3-(benzo[d][1,3]dioxol-5-ylmethylene)-5-methyldihydrofuran-2(3H)-one | 143700-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (E)-3-(benzo[d][1,3]dioxol-5-ylmethylene)-5-methyldihydrofuran-2(3H)-one
• 英文别名: 5-methyl-3-piperonylidene-dihydro-furan-2-one；5-Methyl-3-piperonyliden-dihydro-furan-2-on；(E)-3-(3,4-methylenedioxyphenyl)methylene-5-methyl-dihydro-2(3H)-furanone；(3E)-3-(1,3-benzodioxol-5-ylmethylidene)-5-methyloxolan-2-one
• CAS: 143700-11-2
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: XUMUEYZNCCUCKW-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-pent-4-enoic acid ethyl ester 在 氢氧化钾 、 硫酸 作用下， 以 乙醇 为溶剂， 反应 7.5h， 生成 (E)-3-(benzo[d][1,3]dioxol-5-ylmethylene)-5-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Efficient Synthesis of α ‐Benzylidene‐ γ ‐methyl‐ γ ‐butyrolactones

  摘要：

  A concise synthesis of alpha-benzylidene-gamma-methyl-gamma-butylolactones 5a-g from substituted benzaldehydes is described. Compounds la-g on reaction with phosphorane 2, provide the pentenoates 3a-g, which can be hydrolyzed to the acids 4a-g. The latter are cyclized to the corresponding butyrolactones 5a-g in excellent yields. The pentenoates 3a-g, on acid catalyzed cyclization, also provide 5a-g in very high yields.

  DOI：

  10.1002/1522-2675(200210)85:10<3525::aid-hlca3525>3.0.co;2-#

文献信息

• Calcium(II)- and Triflimide-Catalyzed Intramolecular Hydroacyloxylation of Unactivated Alkenes in Hexafluoroisopropanol
  作者：Chenxiao Qi、Shengwen Yang、Vincent Gandon、David Lebœuf

  DOI：10.1021/acs.orglett.9b02705

  日期：2019.9.20

  hydroacyloxylation of unactivated alkenes, offering a streamlined access to relevant γ-lactones, which features the utilization of either a calcium(II) salt or triflimide as a catalyst in hexafluoroisopropanol. This method could be applied to the synthesis of natural products and the late-stage functionalization of natural and bioactive molecules. Additionally, DFT computations were used to elucidate the twist

  我们报告了未活化烯烃的有效分子内氢酰氧基化作用，提供了对相关γ-内酯的流线型通道，其特征在于利用了钙盐（II）或三氟甲酰亚胺作为六氟异丙醇中的催化剂。该方法可用于天然产物的合成以及天然和生物活性分子的后期功能化。此外，DFT计算用于阐明在未活化烯烃的加氢酰胺化和加氢酰氧基化之间有关5和6元环形成的反应性扭曲。
• Losanitsch, Monatshefte fur Chemie, 1914, vol. 35, p. 303
  作者：Losanitsch

  DOI：——

  日期：——
• US5416224A
  申请人：——

  公开号：US5416224A

  公开（公告）日：1995-05-16
• Efficient Synthesis of <i>α</i> ‐Benzylidene‐ <i>γ</i> ‐methyl‐ <i>γ</i> ‐butyrolactones
  作者：Raghao S. Mali、Kantipudi N. Babu

  DOI：10.1002/1522-2675(200210)85:10<3525::aid-hlca3525>3.0.co;2-#

  日期：2002.10

  A concise synthesis of alpha-benzylidene-gamma-methyl-gamma-butylolactones 5a-g from substituted benzaldehydes is described. Compounds la-g on reaction with phosphorane 2, provide the pentenoates 3a-g, which can be hydrolyzed to the acids 4a-g. The latter are cyclized to the corresponding butyrolactones 5a-g in excellent yields. The pentenoates 3a-g, on acid catalyzed cyclization, also provide 5a-g in very high yields.