2-<3,4-(Methylenedioxy)phenyl>tetrahydrofuran | 52302-44-0

• 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: 2-<3,4-(Methylenedioxy)phenyl>tetrahydrofuran
• 英文别名: 5-(tetrahydrofuran-2-yl)benzo[d][1,3]dioxole；2-<3.4-Methylendioxy-phenyl>-tetrahydrofuran；5-tetrahydro[2]furyl-benzo[1,3]dioxole；5-Tetrahydro[2]furyl-benzo[1,3]dioxol；(3,4-Methylenedioxyphenyl)tetrahydrofuran；5-(oxolan-2-yl)-1,3-benzodioxole
• CAS: 52302-44-0
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: QCJOBFOJNSHFBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  107-109 °C(Press: 0.01 Torr)
• 密度：
  1.2226 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-((phenylthio)methyl)benzo[d][1,3]dioxole 在 正丁基锂 、 tris(2,2'-bipyridyl)ruthenium dichloride 、 四甲基乙二胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 硝基甲烷 、 正己烷 为溶剂， 反应 11.0h， 生成 2-<3,4-(Methylenedioxy)phenyl>tetrahydrofuran
  参考文献：
  名称：

  富电子苯基苄基硫化物的可见光诱导环化：四氢呋喃和四氢吡喃的合成

  摘要：

  描述了一种通过光氧化还原催化过程制备四氢呋喃和四氢吡喃的新方法。苯硫基辅助基团的引入使底物易于氧化以形成用于连续分子内环化的阳离子中间体。该方法反应条件温和，操作简单。

  DOI：

  10.1055/s-0035-1561393

文献信息

• v. Bruchhausen; Lingner, Archiv der Pharmazie, 1957, vol. 290, p. 1,11
  作者：v. Bruchhausen、Lingner

  DOI：——

  日期：——
• Kuraoka; Sugawara, Nippon Kagaku Zasshi, 1958, vol. 79, p. 1161
  作者：Kuraoka、Sugawara

  DOI：——

  日期：——
• Photoinduced Molecular Transformations. 157. A New Stereo- and Regioselective Synthesis of 2,6-Diaryl-3,7-dioxabicyclo[3.3.0]octane Lignans Involving a .beta.-Scission of Alkoxyl Radicals as the Key Step. New Total Syntheses of (.+-.)-Sesamin, (.+-.)-Eudesmin, and (.+-.)-Yangambin
  作者：Hiroshi Suginome、Masataka Ishikawa、Kaoru Yorita、Noriaki Shimoyama、Takahiro Sasaki、Kazuhiko Orito

  DOI：10.1021/jo00115a021

  日期：1995.5

  New total syntheses of naturally occurring 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans, (+/-)-sesamin and (+/-)-eudesmin, and the first total synthesis of (+/-)-yangambin were achieved according to a general method devised by Suginome and colleagues for replacing the carbonyl group of the cyclopentanone ring with an oxygen atom to give a corresponding tetrahydrofuran ring involving a regioselective beta-scission of alkoxyl radicals; arylation of dimethyl, diallyl, or dibenzyl 3,7-dioxobicyclo[3.3.0]octane-2,6-dicarbonate (18 and 19a,b) with aryllead triacetate 9a-c, followed by dealkoxycarbonylation of the resulting arylated product 20a-f, gave 2,6-diaryl-3,7-dioxobicyclo-[3.3.0]octane 21a-c. A regioselective Baeyer-Villiger oxidation of 21a-e with m-CPBA-NaHCO3 or -K2CO3 gave the corresponding delta-lactone 22a-c, which was reduced with DIBAL to give the corresponding lactol 23a-c. The irradiation of a solution of the hypoiodite of 23a-c, generated in situ with mercury(II) oxide-iodine, in benzene with Pyrex-filtered light resulted in a regioselective beta-scission of the corresponding alkoxyl radical to give iodo formate 24a-c. Heating 24a-c in MeOH with NaBH4 gave (+/-)-sesamin (25a), (+/-)-eudesmin (25b), or (+/-)-yangambin (25c).
• DE953878
  申请人：——

  公开号：——

  公开（公告）日：——
• Visible-Light-Induced Cyclization of Electron-Enriched Phenyl Benzyl Sulfides: Synthesis of Tetrahydrofurans and Tetrahydropyrans
  作者：Wujiong Xia、Wei Li、Chao Yang、Guo-Lin Gao

  DOI：10.1055/s-0035-1561393

  日期：——

  A new approach to the preparation of tetrahydrofurans and tetrahydropyrans through a photoredox catalytic process is described. The introduction of a phenylsulfanyl auxiliary group permits the substrates to be readily oxidized to form cationic intermediates for sequential intramolecular cyclization. The method features mild reaction conditions and operational simplicity.

  描述了一种通过光氧化还原催化过程制备四氢呋喃和四氢吡喃的新方法。苯硫基辅助基团的引入使底物易于氧化以形成用于连续分子内环化的阳离子中间体。该方法反应条件温和，操作简单。