2-methylamino-2-thiazoline | 10416-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-methylamino-2-thiazoline
• 英文别名: 2-Methylamino-2-thiazolin；N-Methyl-4,5-dihydro-1,3-thiazol-2-amine；N-methyl-1,3-thiazolidin-2-imine
• CAS: 10416-51-0
• 化学式: C₄H₈N₂S
• mdl: MFCD11109093
• 分子量: 116.187
• InChiKey: KOFXNMVSVWDBKN-UHFFFAOYSA-N

物化性质

• 熔点：
  89-90 °C
• 沸点：
  186.8±23.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methylamino-2-thiazoline 在 溶剂黄146 、 sodium nitrite 作用下， 生成 3-Nitroso-2-methylimino-1,3-thiazolidin
  参考文献：
  名称：

  The Reaction of 2-Amino-Δ²-thiazoline and Related Compounds with Nitrous Acid^1a

  摘要：

  DOI：

  10.1021/jo01020a517
• 作为产物：
  描述：

  N-(2-hydroxyethyl)-N'-methylthiourea 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以87%的产率得到2-methylamino-2-thiazoline
  参考文献：
  名称：

  通过N-（2-羟乙基）-N'-甲基-硫脲的Mitsunobu反应有效合成2-甲基氨基噻唑啉

  摘要：

  通过分子内的Mitsunobu反应从N-（2-羟乙基）-硫脲2选择性地合成2-甲基氨基噻唑啉3。

  DOI：

  10.1016/s0040-4039(99)00457-8

文献信息

• N-Acyl-4,5-dihydro-4,4-dimethyl-N-methyl-2-thiazolamine as a chemoselective acylating agent
  作者：Taek Hyeon Kim、Garp-Yeol Yang

  DOI：10.1016/s0040-4039(02)02414-0

  日期：2002.12

  2-Methylamino-2-thiazoline reacted with alkyl acyl halides to produce N-acyl-2-methylamino-2-thiazolines, exo-acylated product regioselectively, which were found to be highly chemoselective acylating agents for primary amine in the presence of secondary amine and for the less sterically hindered of two different primary amines.

  2-甲基氨基-2-噻唑啉与烷基酰卤反应以产生Ñ酰基-2-甲基氨基-2-噻唑啉，外切-acylated产品区域选择性，这被认为是在仲胺的存在下伯胺高度化学选择性的酰化剂以及两种不同的伯胺在空间上受阻较小。
• Study on the structures of 2-substituted iminothiazolidine derivatives
  作者：Masatoshi Sakae、Masanori Katsurada、Mayumi Watanabe、Fumio Yoneda、Sadao Nishigaki、Toshimasa Ishida

  DOI：10.1002/jhet.5570340125

  日期：1997.1

  together with two kinds of byproducts, 3-(N-methylthiocar-bamoyl)-2-methyliminothiazolidine 4 and N,N′-dimethyl-N-(2-thiazolin-2-yl)thiourea 5. Thermal isomer-ization of 5 to 4 was observed. The structures of the byproducts were confirmed by X-ray crystallography.

  2-溴乙胺1与甲基异硫氰酸酯2在温和的条件下反应，以2-甲基-氨基-2-噻唑啉3为主要产物，并与两种副产物3-（N-甲基硫代氨基苯甲酰基）-2-甲基亚氨基噻唑烷4和N，N′-二甲基-N-（2-噻唑啉-2-基）硫脲5。观察到5至4的热异构化。通过X射线晶体学证实了副产物的结构。
• Studies on thiazoline and thiazolidine derivatives. XI. Synthesis of 3-N-alkylthiocarbamoyl-2-alkyliminothiazolidines.
  作者：YUICHI YAMAMOTO、REIKO YODA、MAKIKO MATSUMURA

  DOI：10.1248/cpb.23.2134

  日期：——

  The compounds synthesized through the route (a) and the route (b) as shown in Chart 1 have been assigned by S. Gabriel in the past and by E. Cherbuliez, et al. recently to Type A, N-alkyl-N'-alkyl-N'-(2-thiazolin-2-yl) thiourea (5). We had some doubt in the structure of the above compounds synthesized through the route (a) and (b), so they were hydrolyzed with 15% H2SO4 to give Type B, 3-N-alkylthiocarbamoyl-2-oxothiazolidine (6) which was assigned with infrared spectrum (IR), Mass Spectra and nuclear magnetic resonance (NMR) data and confirmed by synthesis of 6 through the route (c). Thus, it was confirmed that the compounds obtained by our synthesis through the route (a) and (b) possessed the Type B structure ; 3-N-alkylthiocarbamoyl-2-alkyliminothiazolidine (4), instead of the Type A structure. The data for ultraviolet spectrum (UV), IR, MS and NMR are shown in Table I, II and III.

  通过图1所示的路线(a)和路线(b)合成的化合物过去已由S. Gabriel和E. Cherbuliez等人分配。最近到A型，N-烷基-N'-烷基-N'-(2-噻唑啉-2-基)硫脲(5)。我们对上述路线(a)和(b)合成的化合物的结构有些疑问，因此用15% H2SO4水解得到B型，3-N-烷硫基氨基甲酰基-2-氧代噻唑烷(6)，即用红外光谱(IR)、质谱和核磁共振(NMR)数据指定并通过路线(c)合成6来证实。由此，证实我们通过路线(a)和(b)合成得到的化合物具有B型结构； 3-N-烷硫基氨基甲酰基-2-烷基亚氨基噻唑烷(4)，代替A型结构。紫外光谱(UV)、IR、MS和NMR的数据如表I、II和III所示。
• Cinnamides as selective small-molecule inhibitors of a cellular model of breast cancer stem cells
  作者：Andrew R. Germain、Leigh C. Carmody、Partha P. Nag、Barbara Morgan、Lynn VerPlank、Cristina Fernandez、Etienne Donckele、Yuxiong Feng、Jose R. Perez、Sivaraman Dandapani、Michelle Palmer、Eric S. Lander、Piyush B. Gupta、Stuart L. Schreiber、Benito Munoz

  DOI：10.1016/j.bmcl.2013.01.025

  日期：2013.3

  A high-throughput screen (HTS) was conducted against stably propagated cancer stem cell (CSC)-enriched populations using a library of 300,718 compounds from the National Institutes of Health (NIH) Molecular Libraries Small Molecule Repository (MLSMR). A cinnamide analog displayed greater than 20-fold selective inhibition of the breast CSC-like cell line (HMLE_sh_Ecad) over the isogenic control cell line (HMLE_sh_eGFP). Herein, we report structure-activity relationships of this class of cinnamides for selective lethality towards CSC-enriched populations. (C) 2013 Published by Elsevier Ltd.
• Mizrakh, L. I.; Polonskaya, L. Yu.; Gvozdetskii, A. N., Journal of general chemistry of the USSR, 1988, vol. 58, # 10, p. 1999 - 2003
  作者：Mizrakh, L. I.、Polonskaya, L. Yu.、Gvozdetskii, A. N.、Vasil'ev, A. M.、Karpunina, L. B.

  DOI：——

  日期：——