(Z)-3-butylsulfanyl-6-(4-chlorophenyl)-2-methylhex-3-en-5-yn-2-ol | 1403835-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-butylsulfanyl-6-(4-chlorophenyl)-2-methylhex-3-en-5-yn-2-ol
• CAS: 1403835-78-8
• 化学式: C₁₇H₂₁ClOS
• 分子量: 308.872
• InChiKey: BUSJSZHHXYNWOW-PXNMLYILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-3-butylsulfanyl-6-(4-chlorophenyl)-2-methylhex-3-en-5-yn-2-ol 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以78%的产率得到2-(5-(4-chlorophenyl)-4-iodothiophen-2-yl)propan-2-ol
  参考文献：
  名称：

  Synthesis of 3-iodothiophenes via iodocyclization of (Z)-thiobutenynes

  摘要：

  A simple synthesis of 3-iodothiophenes was demonstrated using a wide range of (Z)-thioenynes. The key step in the iodocyclofunctionalization was the selective reduction of the triple bond in (Z)-thioenynes by the addition of iodine as an electrophilic agent. The 3-iodothiophenes were obtained in good to excellent yields of 61-92%. The 3-iodothiophenes were used as substrates in Sonogashira cross-coupling reactions to obtain thiophene acetylenes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.118
• 作为产物：
  描述：

  丁硫醇 、 6-(4-chlorophenyl)-2-methylhexa-3,5-diyn-2-ol 在 四丁基氢氧化铵 作用下， 以 乙醇 、 水 为溶剂， 以92%的产率得到(Z)-3-butylsulfanyl-6-(4-chlorophenyl)-2-methylhex-3-en-5-yn-2-ol
  参考文献：
  名称：

  Improvement in the synthesis of (Z)-organylthioenynes via hydrothiolation of buta-1,3-diynes: a comparative study using NaOH or TBAOH as base

  摘要：

  Hydrothiolation of symmetrical and unsymmetrical buta-1,3-diynes with sodium organylthiolate anions in reflux, generated in situ by reacting C4H9SH with NaOH, afforded (Z)-organylthioenynes in low to good yields (25-80%). By using tetrabutylammonium hydroxide (TBAOH) as base instead of NaOH, the hydrothiolation of buta-1,3-diynes was more rapid and efficient, providing (Z)-organylthioenynes in good to excellent yields (70-95%). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.003

文献信息

• Improvement in the synthesis of (Z)-organylthioenynes via hydrothiolation of buta-1,3-diynes: a comparative study using NaOH or TBAOH as base
  作者：Amanda S. Santana、Diego B. Carvalho、Nadla S. Casemiro、Gabriela R. Hurtado、Luiz H. Viana、Nájla M. Kassab、Sandro L. Barbosa、Francisco A. Marques、Palimécio G. Guerrero、Adriano C.M. Baroni

  DOI：10.1016/j.tetlet.2012.08.003

  日期：2012.10

  Hydrothiolation of symmetrical and unsymmetrical buta-1,3-diynes with sodium organylthiolate anions in reflux, generated in situ by reacting C4H9SH with NaOH, afforded (Z)-organylthioenynes in low to good yields (25-80%). By using tetrabutylammonium hydroxide (TBAOH) as base instead of NaOH, the hydrothiolation of buta-1,3-diynes was more rapid and efficient, providing (Z)-organylthioenynes in good to excellent yields (70-95%). (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of 3-iodothiophenes via iodocyclization of (Z)-thiobutenynes
  作者：Amanda S. Santana、Diego B. Carvalho、Nadla S. Cassemiro、Luiz H. Viana、Gabriela R. Hurtado、Marcos S. Amaral、Najla M. Kassab、Palimécio G. Guerrero、Sandro L. Barbosa、Miguel J. Dabdoub、Adriano C.M. Baroni

  DOI：10.1016/j.tetlet.2013.10.118

  日期：2014.1

  A simple synthesis of 3-iodothiophenes was demonstrated using a wide range of (Z)-thioenynes. The key step in the iodocyclofunctionalization was the selective reduction of the triple bond in (Z)-thioenynes by the addition of iodine as an electrophilic agent. The 3-iodothiophenes were obtained in good to excellent yields of 61-92%. The 3-iodothiophenes were used as substrates in Sonogashira cross-coupling reactions to obtain thiophene acetylenes. (C) 2013 Elsevier Ltd. All rights reserved.