prop-2-ynyl N-cyclohexyl-2-methoxybuta-2,3-dienimidothioate | 1600501-20-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚氨硫酯类
• 英文名称: prop-2-ynyl N-cyclohexyl-2-methoxybuta-2,3-dienimidothioate
• CAS: 1600501-20-9
• 化学式: C₁₄H₁₉NOS
• 分子量: 249.377
• InChiKey: PPBNALWSHGSNMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  prop-2-ynyl N-cyclohexyl-2-methoxybuta-2,3-dienimidothioate 反应 0.17h， 以96%的产率得到N-cyclohexyliden-2-methoxy-1-(prop-2-ynylsulfanyl)buta-1,3-dien-1-amine
  参考文献：
  名称：

  Structural reorganization of (allyl-, benzyl-, and propargylsulfanyl)-substituted 2-aza-1,3,5-trienes in t-BuOK/THF/DMSO: access to rare functionalized 2-thiazolines

  摘要：

  Treatment of (allyl-, benzyl-, and propargylsulfanyl)-substituted 2-aza-1,3,5-trienes, which are readily accessible from lithiated methoxyallene, isopropyl isothiocyanate, and allyl, benzyl, or propargyl bromide, respectively, with t-BuOK in THF/DMSO resulted in the unexpected formation of 2-thiazoline derivatives along with seven-membered azaheterocycles [in the case of (allyl- and benzylsulfanyl)-substituted 2-aza-1,3,5-trienes]. An unprecedented structural reorganization of the azatrienes into 2-thiazolines presumably occurs via alpha-deprotonation of the substituents at the sulfur atom followed by intramolecular [1,5]-cyclization. Deprotonation of the ketimine fragment of the same molecule followed by [1,71-electrocyclization resulted in azepine ring formation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.015
• 作为产物：
  描述：

  1-甲氧基-1,2-丙二烯 、 3-溴丙炔 、 环己基异硫氰酸脂 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 prop-2-ynyl N-cyclohexyl-2-methoxybuta-2,3-dienimidothioate
  参考文献：
  名称：

  Structural reorganization of (allyl-, benzyl-, and propargylsulfanyl)-substituted 2-aza-1,3,5-trienes in t-BuOK/THF/DMSO: access to rare functionalized 2-thiazolines

  摘要：

  Treatment of (allyl-, benzyl-, and propargylsulfanyl)-substituted 2-aza-1,3,5-trienes, which are readily accessible from lithiated methoxyallene, isopropyl isothiocyanate, and allyl, benzyl, or propargyl bromide, respectively, with t-BuOK in THF/DMSO resulted in the unexpected formation of 2-thiazoline derivatives along with seven-membered azaheterocycles [in the case of (allyl- and benzylsulfanyl)-substituted 2-aza-1,3,5-trienes]. An unprecedented structural reorganization of the azatrienes into 2-thiazolines presumably occurs via alpha-deprotonation of the substituents at the sulfur atom followed by intramolecular [1,5]-cyclization. Deprotonation of the ketimine fragment of the same molecule followed by [1,71-electrocyclization resulted in azepine ring formation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.015

文献信息

• (Propargylsulfanyl)-2-aza-1,3,5-trienes as a direct source for novel family of highly functionalized 4,5-dihydro-1,3-thiazoles
  作者：Nina A. Nedolya、Ol'ga A. Tarasova、Alexander I. Albanov、Lyudmila V. Klyba、Boris A. Trofimov

  DOI：10.1016/j.tet.2016.12.064

  日期：2017.2

  2-(1-alkoxyprop-1-enyl)-5-ethenylidene-4,5-dihydro-1,3-thiazoles has been disclosed through the reaction of (propargylsulfanyl)-2-aza-1,3,5-trienes (readily available from alkoxyallenes, isothiocyanates, and propargyl bromide) with potassium or sodium tert-butoxide (1.1–1.4 equiv) under mild conditions [DMSO/THF (∼1:4–5), ca. −30 °C, 15–30 min]. The process proceeds through deprotonation of an activated SCH2 group

  通过（炔丙基硫烷基）-2-氮杂-1的反应，已经公开了一种新颖的，简单的2-（1-烷氧基丙-1-烯基）-5-乙烯基-1,4-亚乙基-1,3-噻唑的方法。在温和条件下[ 3,5-三烯（可从烷氧基烯，异硫氰酸酯和炔丙基溴中得到）]与叔丁醇钾或叔丁醇钠（1.1-1.4当量）[DMSO / THF（〜1：4-5），约。−30°C，15–30分钟]。该过程通过激活的SCH 2基团的去质子化，然后进行分子内[1,5]环闭合来进行。与烷基，苄基和烯丙基硫烷基类似物不同，未观察到七元氮杂杂环的排他性或竞争性形成。