5-甲基-2-苯基-4,5-二氢-1,3-噻唑 | 23062-75-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-甲基-2-苯基-4,5-二氢-1,3-噻唑
• 英文名称: 5-Methyl-2-phenyl-2-thiazoline
• 英文别名: phenyl-2 methyl-5 thiazoline；5-methyl-2-phenylthiazoline；5-methyl-2-phenyl-4,5-dihydro-thiazole；5-Methyl-2-phenyl-4,5-dihydro-thiazol；2-Phenyl-5-methyl-2-thiazolin；5-methyl-2-phenyl-4,5-dihydro-1,3-thiazole
• CAS: 23062-75-1
• 化学式: C₁₀H₁₁NS
• 分子量: 177.27
• InChiKey: ICCYFBRBECDTKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  5-甲基-2-苯基-4,5-二氢-1,3-噻唑 生成 甲基半胱胺
  参考文献：
  名称：

  The Cyclization of N-Alkenylthionamides to Thiazolines and Dihydrothiazines

  摘要：

  DOI：

  10.1021/jo01063a038
• 作为产物：
  描述：

  N-丙-2-烯基苯甲酰胺 在 对甲苯磺酸 劳森试剂 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 23.0h， 生成 5-甲基-2-苯基-4,5-二氢-1,3-噻唑
  参考文献：
  名称：

  Organoselenium- and proton-mediated cyclization reactions of allylic amides and thioamides. Syntheses of 2-oxazolines and 2-thiazolines

  摘要：

  A variety of allylic amides and thioamides were treated with phenylselenenyl bromide in chloroform to give, via 5-exo cyclization, 2-oxazolines and 2-thiazolines, respectively, carrying a (phenylselenenyl)methyl substituent in the 5-position. In some cases (N-crotyl- and N-cinnamylamides/thioamides), dihydro-1,3-oxazines/-thiazines were formed via 6-endo cyclization. The phenylselenenyl group of the cyclofunctionalization products was slowly eliminated by treatment with m-chloroperbenzoic acid to introduce unsaturation in the resulting oxazoline/thiazoline. Reductive removal of the phenylselenenyl group was effected by treatment with triphenyltin hydride. This reaction was sometimes accompanied by a rearrangement of the heterocyclic ring. Proton-induced cyclizations of allylic thioamides to give 2-thiazolines was slowly but efficiently effected in boiling toluene containing a catalytic amount of p-toluenesulfonic acid.

  DOI：

  10.1021/jo00010a045

文献信息

• Thioenamide photochemistry
  作者：Axel Couture、Regine Dubiez、Alain Lableche-Combier

  DOI：10.1039/c39820000842

  日期：——

  In contrast with their oxo-analogues, thioenamides undergo photochemical cyclization to yield isoquinolinethione derivatives which are easily converted into isoquinolones and tetrahydroisoquinolines by treatment with benzeneseleninic anhydride and EtO3BF4–NaBH4, respectively.

  与它们的羰基类似物相反，硫烯酰胺经过光化学环化反应生成异喹啉硫酮衍生物，通过分别用苯硒二酸酐和EtO 3 BF 4 -NaBH 4处理，异硫氰酸衍生物很容易转化为异喹啉酮和四氢异喹啉。
• Divergent regioselectivity in photoredox-catalyzed hydrofunctionalization reactions of unsaturated amides and thioamides
  作者：Peter D. Morse、David A. Nicewicz

  DOI：10.1039/c4sc02331e

  日期：——

  A direct method to construct 2-oxazolines and 2-thiazolines from corresponding allylic amides and thioamides is reported. The redox-neutral intramolecular hydrofunctionalization is enabled by a dual catalyst system comprised of 9-mesityl-N-methyl acridinium tetrafluoroborate and phenyl disulphide and exhibits complete selectivity for the anti-Markovnikov regioisomeric products. The cyclization of allylic

  报道了从相应的烯丙基酰胺和硫代酰胺构建2-恶唑啉和2-噻唑啉的直接方法。氧化还原中性分子内氢官能化是通过由9-异三甲苯基-N-甲基吖啶鎓四氟硼酸盐和二硫化苯基组成的双催化剂系统实现的，并且对反马尔可夫尼科夫区域异构产物表现出完全选择性。假设烯丙基硫代酰胺的环化是通过改进的机制进行的，其中硫代酰胺的氧化而不是烯烃的氧化导致了观察到的反应性。
• Robbe; Fernandez; Chapat, European Journal of Medicinal Chemistry, 1985, vol. 20, # 1, p. 16 - 24
  作者：Robbe、Fernandez、Chapat、et al.

  DOI：——

  日期：——
• Reaction of (1,ω)-<i>N</i>-Acylamino Alcohols with Lawesson's Reagent:  Synthesis of Sulfur-Containing Heterocycles
  作者：Takehiko Nishio

  DOI：10.1021/jo961704n

  日期：1997.2.1

  Lawesson's reagent [LR: 2,4-bis(p-methoxyphenyl)-1,3,2,4-dithiaphosphetane 2,4-disulfide] is shown to be a valuable reagent for the ready access of sulfur-containing heterocycles: thiazolines 2 starting from the (1,2)-N-acylamino alcohols 1 and benzothiazines 14 from [2-(N-acylamino)phenyl]alkanols 12. Treatment of (1,2)-N-acylamino secondary alcohols 1a-p with LR gave the thiazolines 1a-p via direct conversion of the alcohols to the respective thiols, and the subsequent thionation of the amide carbonyl, followed by cyclization with the elimination of hydrogen sulfide. However, reaction of (1,2)-N-acylamino tertiary alcohols 1q-u with LR yielded the dehydration products 5-7 and 9. Treatment of [2-(N-acylamino)phenyl]alkanols 12a-f with a molar equivalent of LR yielded the 3,1-benzothiazines 14a-f. In this reaction, the [2-(N-acylamino)phenyl]alkanethiols 13a-e were isolated when the corresponding alcohols 12a-e were treated with 0.5 equiv of LR. Further thionation of 13c with LR also gave 3,1-benzothiazine 14c.
• Salomon, Chemische Berichte, 1893, vol. 26, p. 1322
  作者：Salomon

  DOI：——

  日期：——