| 163579-73-5

• CAS: 163579-73-5；200074-54-0；135571-90-3；200074-56-2；200074-55-1
• 化学式: C₁₃H₁₂O₄W
• 分子量: 416.086
• InChiKey: UMQVPYXUPRQRPG-OUTKXMMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  在 CF₃SO₃H 、 CF₃COOH 作用下， 以90%的产率得到
  参考文献：
  名称：

  Stereochemical Course in Tungsten-Promoted Cyclocarbonylation Reactions To Form Five-, Six-, and Seven-Membered Lactone Rings

  摘要：

  DOI：

  10.1021/ja00115a031

文献信息

• Tungsten-Promoted Intramolecular Alkoxycarbonylation for Synthesis of Complex Oxygenated Molecules
  作者：Chi-Chung Chen、Jang-Shyang Fan、Su-Ju Shieh、Gene-Hsian Lee、Shie-Ming Peng、Sue-Lang Wang、Rai-Shung Liu

  DOI：10.1021/ja9617808

  日期：1996.1.1

  Intramolecular alkoxycarbonylation of tungsten-propargyl compounds proceeds with excellent diastereoselectivities to form eta(3)-delta- and -epsilon-lactones but for gamma-lactones. With OSi(t-Bu)Me(2) substituted for an or-hydroxy group, eta(3)-gamma-lactones are stereoselectively formed with syn stereoselection. An optically active tungsten eta(3)-gamma-lactone is prepared from D-(+)-xylose to illustrate the stereochemical effect of OSi(t-Bu)Me(2). All these eta(3)-gamma-, -delta-, and -epsilon-lactones are converted to allyl anions that react in situ with aldehydes and ketones to produce various beta-(hydroxylalkyl)-alpha-methylene-gamma-lactones with good diastereoselectivity. This reaction is also applied to the synthesis of chiral alpha-methylene butyrolactones. Organic carbonyls add to the pi-allyl groups of eta(3)-gamma- and -delta-lactones opposite the tungsten fragment, whereas additions occur from the metal side for eta(3)-epsilon-lactones. The stereochemical courses of these reactions are discussed in detail. These two tungsten-promoted reactions efficiently effect stereoselective transformation of chloroalkynols to complex alpha-methylene-gamma-lactones, which are useful materials for syntheses of trisubstituted 1,3-, 1,4-, and 1-5-diols.
• Enantioselective syntheses of α-methylene butyrolactones via asymmetric aminocarbonylation of tungsten–prop-2-ynyl compounds
  作者：Lin Hung Shiu、Sue-Lein Wang、Rai-Shung Liu、Lin Hung Shiu、Ming-Jung Wu

  DOI：10.1039/a706309a

  日期：——

  A tungsten–η1-vinylprop-2-ynyl compound undergoes enantioselective aminocarbonylation to afford an optically pure tungsten–π-γ-lactone; this π-allyl complex is useful for the efficient synthesis of optically pure α-methylene butyrolactone.