7-(mercaptomethyl)trideca-5,8-diyn-7-ol | 1393655-55-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(mercaptomethyl)trideca-5,8-diyn-7-ol
• 英文别名: 7-mercaptomethyl-trideca-5,8-diyn-7-ol；7-(Sulfanylmethyl)trideca-5,8-diyn-7-ol；7-(sulfanylmethyl)trideca-5,8-diyn-7-ol
• CAS: 1393655-55-4
• 化学式: C₁₄H₂₂OS
• 分子量: 238.394
• InChiKey: BGTBCBOWRHWTLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  21.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(mercaptomethyl)trideca-5,8-diyn-7-ol 在 potassium iodide 、 palladium(II) iodide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以52%的产率得到2-butyl-4-hex-1-ynylthiophene
  参考文献：
  名称：

  Synthesis of Substituted Thiophenes by Palladium-Catalyzed Heterocyclodehydration of 1-Mercapto-3-yn-2-ols in Conventional and Nonconventional Solvents

  摘要：

  A variety of readily available 1-mercapto-3-yn-2-ols 5 were conveniently converted into the corresponding thiophenes 6 in good to high yields in MeOH as the solvent at 50-100 degrees C in the presence of catalytic amounts (1-2%) of PdI2 in conjunction with KI (KI:PdI2 molar ratio = 10). The catalyst could be made recyclable employing an ionic liquid, such as BmimBF(4), as the solvent under suitable conditions.

  DOI：

  10.1021/jo301943k
• 作为产物：
  描述：

  巯基乙酸乙酯 、 1-己炔 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 4.25h， 以51%的产率得到7-(mercaptomethyl)trideca-5,8-diyn-7-ol
  参考文献：
  名称：

  An Iodocyclization Approach to Substituted 3-Iodothiophenes

  摘要：

  A novel approach to 3-iodothiophenes by direct iodocyclization of alkynylthiol derivatives is presented. A variety of 1-mercapto-3-yn-2-ols 5 (readily available from alkynylation of the corresponding alpha-mercapto ketones or alpha-mercapto esters) were smoothly converted into the corresponding 3-iodothiophene derivatives 6 in good yields by reaction with molecular iodine in the presence of NaHCO3 at room temperature in MeCN as the solvent.

  DOI：

  10.1021/jo301001j

文献信息

• An Iodocyclization Approach to Substituted 3-Iodothiophenes
  作者：Bartolo Gabriele、Raffaella Mancuso、Giuseppe Salerno、Richard C. Larock

  DOI：10.1021/jo301001j

  日期：2012.9.7

  A novel approach to 3-iodothiophenes by direct iodocyclization of alkynylthiol derivatives is presented. A variety of 1-mercapto-3-yn-2-ols 5 (readily available from alkynylation of the corresponding alpha-mercapto ketones or alpha-mercapto esters) were smoothly converted into the corresponding 3-iodothiophene derivatives 6 in good yields by reaction with molecular iodine in the presence of NaHCO3 at room temperature in MeCN as the solvent.
• Synthesis of Substituted Thiophenes by Palladium-Catalyzed Heterocyclodehydration of 1-Mercapto-3-yn-2-ols in Conventional and Nonconventional Solvents
  作者：Bartolo Gabriele、Raffaella Mancuso、Lucia Veltri、Vito Maltese、Giuseppe Salerno

  DOI：10.1021/jo301943k

  日期：2012.11.2

  A variety of readily available 1-mercapto-3-yn-2-ols 5 were conveniently converted into the corresponding thiophenes 6 in good to high yields in MeOH as the solvent at 50-100 degrees C in the presence of catalytic amounts (1-2%) of PdI2 in conjunction with KI (KI:PdI2 molar ratio = 10). The catalyst could be made recyclable employing an ionic liquid, such as BmimBF(4), as the solvent under suitable conditions.