2-(3,4-(methylenedioxy)phenyl)-3-(hydroxymethyl)-4-methylenetetrahydrofuran | 144918-19-4

• 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)-3-(hydroxymethyl)-4-methylenetetrahydrofuran
• CAS: 144918-19-4
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: SGJHUJIFVKIDQW-MFKMUULPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(3,4-(methylenedioxy)phenyl)-3-(hydroxymethyl)-4-methylenetetrahydrofuran 在 咪唑 、 4-二甲氨基吡啶 、 sodium hydroxide 、 草酰氯 、 四丁基氟化铵 、 双氧水 、 二甲基亚砜 、 三乙胺 、 diborane(6) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 29.5h， 生成 (+/-)-Samin
  参考文献：
  名称：

  Stereoselective total synthesis of (±)-Samin, the general furofuran lignan precursor

  摘要：

  A concise stereoselective synthesis of the general furofuran lignan precursor (+/-)-Samin 1 has been achieved through a radical annulation reaction in good overall yield.

  DOI：

  10.1016/s0040-4039(00)73480-0
• 作为产物：
  描述：

  1-(3,4-(methylenedioxy)phenyl)-1-(prop-2-ynyloxy)-2,3-epoxypropane 在 二氯二茂钛 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以76%的产率得到2-(3,4-(methylenedioxy)phenyl)-3-(hydroxymethyl)-4-methylenetetrahydrofuran
  参考文献：
  名称：

  Stereoselective Synthesis of Polysubstituted Tetrahydrofurans by Radical Cyclization of Epoxides Using a Transition-Metal Radical Source. Application to the Total Synthesis of (±)-Methylenolactocin and (±)-Protolichesterinic Acid

  摘要：

  Radical cyclization reactions of substituted alpha-(prop-2-ynyloxy) epoxides using bis(cyclopentadienyl)-titanium(III) chloride as the radical source resulted in polysubstituted tetrahydrofurans. Titanium(III) species were prepared in situ from commercially available titanocene dichloride and zinc dust in tetrahydrofuran, Upon radical cyclization, 2-aryl epoxides 3a-e afforded only trans products 4a-e whereas the 2-alkyl epoxides 3f-h formed a mixture of isomeric products 4f-h in a ratio of 5:1. Some of the aryl tetrahydrofuran derivatives have already been used for the synthesis of bioactive furofuran lignans. 2-Pentyl-3-(hydroxymethyl)-4-methylenetetrahydrofuran (4f) and 2-tridecyl-3-(hydroxymethyl)-4-methylenetetrahydrofuran (4g) have been transformed to two antitumor antibiotics (+/-)-methylenolactocin (1f) and (+/-)-protolichesterinic acid (1g), respectively, in good overall yield.

  DOI：

  10.1021/jo971526d

文献信息

• Stereoselective total synthesis of (±)-Paulownin and (±)-Isogmelinol through radical annulation route
  作者：Subhas Chandra Roy、Sankar Adhikari

  DOI：10.1016/s0040-4020(01)81924-4

  日期：1993.1

  A highly stereocontrolled synthesis of furofuran lignans, (±)-Paulownin (1a) and (±)-Isogmelinol (1b) is described involving intramolecular radical cyclisation as a key step.

  呋喃呋喃木脂素，（±）-泡桐（1a）和（±）-异美浓醇（1b）的高度立体控制合成被描述为涉及分子内自由基环化的关键步骤。
• Stereoselective radical annulation route to the synthesis of (±)-paulownin and (±)-isogmelinol
  作者：Sankar Adhikari、Subhas Roy

  DOI：10.1016/s0040-4039(00)61118-8

  日期：1992.9

  A highly stereocontrolled synthesis of (+/-)-paulownin (1a) and (+/-)-isogmelinol (1b) is reported involving intramolecular radical cyclisation reaction as a key step.
• Stereoselective total synthesis of (±)-samin and the dimethoxy analogue, the general furofuran lignan precursors
  作者：Gourhari Maiti、Sankar Adhikari、Subhas Chandra Roy

  DOI：10.1016/0040-4020(95)00450-m

  日期：1995.7

  A concise stereoselective synthesis of the general furofuran lignan precursors (+/-)-Samin 1a and its dimethoxy analogue 1b has been achieved through a radical annulation reaction in good overall yield.