7-Chloro-2-methylhept-5-yn-3-ol | 182324-27-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-Chloro-2-methylhept-5-yn-3-ol
• CAS: 182324-27-2
• 化学式: C₈H₁₃ClO
• mdl: MFCD19234043
• 分子量: 160.644
• InChiKey: ZRZMOYBNFLMKDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Na[W(CO)3(cyclopentadienyl)] 、 7-Chloro-2-methylhept-5-yn-3-ol 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.
• Stereochemical Course in Tungsten-Promoted Cyclocarbonylation Reactions To Form Five-, Six-, and Seven-Membered Lactone Rings
  作者：Chi-Chung Chen、Jang-Shyang Fan、Gene-Hsian Lee、Shie-Ming Peng、Sue-Lang Wang、Rai-Shung Liu

  DOI：10.1021/ja00115a031

  日期：1995.3