Z-2-Methyl-3-thiocyanatocrotonaldehyd | 49571-43-9

• 分子结构分类: 有机化合物
• 英文名称: Z-2-Methyl-3-thiocyanatocrotonaldehyd
• 英文别名: 2-Methyl-3-thiocyanatocrotonaldehyde；(Z)-α-β-Dimethyl-β-thiocyanato-vinylaldehyd；Z-α-Methyl-β-thiocyanato-crotonaldehyd；2,3-Dimethyl-3-thiocyanatopropenal；[(Z)-3-methyl-4-oxobut-2-en-2-yl] thiocyanate
• CAS: 49571-43-9
• 化学式: C₆H₇NOS
• 分子量: 141.194
• InChiKey: DYOYHSLVTLMKKQ-WAYWQWQTSA-N

物化性质

• 沸点：
  259.1±32.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Z-2-Methyl-3-thiocyanatocrotonaldehyd 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 45.0h， 生成 2-(2,6-dichlorophenyl)-2,3-dihydro-3-hydroperoxy-4,5-dimethylisothiazole 1,1-dioxide
  参考文献：
  名称：

  Synthesis of Monocyclic Hydroperoxy- and Hydroxy-Substituted Sulfin- and Sulfonamides by Oxidation of 4,5-Dimethylisothiazolium Salts

  摘要：

  The isothiazolium salts 10, easily accessible by cyclocondensation of the thiocyanates 8 with the anilines 9, yielded with H,02 as the oxidant the first stable hydroperoxides of the 2-aryl-2,3-dihydroisothiazole 1-oxides rac-cis-13, the 1,1-dioxides 15, and their reduced 3-hydroxy derivatives rac-cis-14 and 16, respectively. The oxidation of 10 to new isothiazol-3(2H)-one 1,1-dioxides (17) is also described. For the first time, an aryl-bridged bis[isothiazolium salt] 11 was synthesized and oxidized.

  DOI：

  10.1002/1522-2675(200201)85:1<183::aid-hlca183>3.0.co;2-5

文献信息

• Synthesis and elastase-inhibiting activity of 2-pyridinyl-isothiazol-3(2H)-one 1,1-dioxides
  作者：Alexander Eilfeld、Camino M. González Tanarro、Maxim Frizler、Joachim Sieler、Bärbel Schulze、Michael Gütschow

  DOI：10.1016/j.bmc.2008.07.049

  日期：2008.9

  The synthesis of a series of new isothiazol-3(2H)-one 1,1-dioxides with halogenated (mostly fluorinated) pyridinyl and pentafluorophenyl substituents at 2-position is reported. These compounds (18-24) became easily accessible from 2-thiocyanato-1-carboxaldehydes and aminopyridines, pentafluoroaniline, respectively, by an isothiazolium cyclization-oxidation route. Compound 21 exhibited an IC(50) value

  报道了一系列新的异噻唑-3（2H）-1，1-二氧化物与2-位卤代（大部分氟化）吡啶基和五氟苯基取代基的合成。这些化合物（18-24）可以通过异噻唑鎓环化-氧化途径轻松地分别从2-thiocyanato-1-caraldehydes和氨基吡啶，五氟苯胺获得。化合物21对人白细胞弹性蛋白酶的IC（50）值为3.1 microM。蛋白酶组织蛋白酶G，胰蛋白酶，组织蛋白酶L和血管紧张素转化酶以及丝氨酸酯酶乙酰胆碱酯酶和胆固醇酯酶均不受21的抑制。
• Synthesis of 2-Phenylisothiazol-3(2H)-One 1,1-Dioxides: Inhibitors of Human Leukocyte Elastase
  作者：Michael Gütschow、Markus Pietsch、Kathleen Taubert、Tonia H. E. Freysoldt、Bärbel Schulze

  DOI：10.1515/znb-2003-0115

  日期：2003.1.1

  Abstract A series of 2-phenylisothiazol-3(2H)-one 1,1-dioxides 14a - q were synthesized by oxidation of isothiazolium perchlorates 12. The inhibition of the serine proteases cathepsin G, chymotrypsin and human leukocyte elastase (HLE) by 14 was investigated. Some 4,5-diphenyl substituted derivatives ( 14i - k) were found to inhibit HLE in a time-dependent manner and exhibited kobs/[I] values > 500

  摘要 通过氧化异噻唑鎓高氯酸盐 12 合成了一系列 2-苯基异噻唑-3(2H)-one 1,1-二氧化物 14a - q。14 对丝氨酸蛋白酶组织蛋白酶 G、糜蛋白酶和人白细胞弹性蛋白酶 (HLE) 的抑制作用被调查。发现一些 4,5-二苯基取代的衍生物 (14i - k) 以时间依赖性方式抑制 HLE，并表现出 kobs/[I] 值 > 500 M-1s-1。14k (kobs/[I] = 2400 M−1s−1)，是该系列中最有效的 HLE 抑制剂。动力学研究得出的结论是，2-苯基异噻唑-3(2H)-one 1,1-二氧化物在活性位点和另一个结合位点与 HLE 相互作用，导致复杂类型的抑制。
• Nitrogen-15 NMR, 2D NMR and ESCA characterization of a new stable 6a-thia(SIV)-1,6-diazapentalene
  作者：Lutz Weber、Rüdiger Szargan、Bärbel Schulze、Manfred Mühlstädt

  DOI：10.1002/mrc.1260280507

  日期：1990.5

  2‐methyl‐3‐thiocyanatocrotonaldehyde with aniline hydrochloride and subsequent addition of dicyclohexylamine afforded a new 6a‐thia(SIV)‐1,6‐diazapentalene. The presence of the NSN bond was verified through the N 1s and S 2p binding energies and the nitrogen‐nitrogen coupling constant in the doubly 15N‐labelled compound, prepared by using [15N]aniline hydrochloride.

  2-甲基-3-硫氰基巴豆醛与盐酸苯胺反应，随后加入二环己胺，得到新的 6a-硫杂 (SIV)-1,6-二氮杂戊烯。NSN键的存在是通过使用[15N]苯胺盐酸盐制备的双15N标记化合物中的N 1s和S 2p结合能和氮-氮偶联常数来验证的。
• Synthesis of N,N′-Linked Bisazaheterocycles with Sulfonamide Structure via Oxidation of S,N-Heteroaromatic Cations
  作者：Bärbel Schulze、Valerija Zakharova、Camino González Tanarro、Michael Gütschow、Lothar Hennig、Joachim Sieler

  DOI：10.1055/s-2008-1066984

  日期：——

  3-hydroperoxy-, 3-hydroxy- and 3-oxoisothiazole 1,1-dioxides have been synthesized by the sequence of oxidation reactions from N,N′-linked isothiazolium perchlorates with hydrogen peroxide, MMPP, and pyridinium dichromate. Isothiazolium salts without acceptor substituents did not give N-substituted sultams. Novel N,N′-bisazaheterocycles were investigated as inhibitors of acetylcholinesterase (AChE) and human leukocyte

  N-邻苯二甲酰亚胺基和 N-喹唑啉基取代的 3-氢过氧、3-羟基和 3-氧代异噻唑 1,1-二氧化物已通过 N,N'-连接的高氯酸异噻唑鎓与过氧化氢的一系列氧化反应合成， MMPP和重铬酸吡啶鎓。没有受体取代基的异噻唑盐不产生N-取代的磺胺嘧啶。研究了新型 N,N'-双氮杂杂环化合物作为乙酰胆碱酯酶 (AChE) 和人白细胞弹性蛋白酶 (HLE) 的抑制剂。发现两种 2,3-dihydro-3-hydroperoxy-2-(phthalimid-1-yl)isothiazole 1,1-dioxides 可抑制 AChE。
• Schulze, Baerbel; Hilbig, Jens; Weber, Lutz, Zeitschrift fur Chemie, 1988, vol. 28, # 8, p. 287 - 288
  作者：Schulze, Baerbel、Hilbig, Jens、Weber, Lutz、Rosenbaum, Karen、Muehlstaedt, Manfred

  DOI：——

  日期：——