(R)-5-(tert-butyldiphenylsiloxy)methylpyrrolidin-2-thione | 142890-14-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-5-(tert-butyldiphenylsiloxy)methylpyrrolidin-2-thione
• 英文别名: (5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]pyrrolidine-2-thione
• CAS: 142890-14-0
• 化学式: C₂₁H₂₇NOSSi
• 分子量: 369.603
• InChiKey: WODZCUOBHXYEJJ-QGZVFWFLSA-N

物化性质

• 熔点：
  116-117 °C(Solv: hexane (110-54-3))
• 沸点：
  434.2±41.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-5-(tert-butyldiphenylsiloxy)methylpyrrolidin-2-thione 在 盐酸 、 sodium hydroxide 、 正丁基锂 、 四丁基氟化铵 、 氢溴酸 、 双氧水 、 四丁基硫酸氢铵 、 氯化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 187.5h， 生成 [(R)-2-(4-Fluoro-phenyl)-3-(2-propylamino-pyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-5-yl]-methanol
  参考文献：
  名称：

  The neuroprotective action of JNK3 inhibitors based on the 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole scaffold

  摘要：

  Imidazole-based structures of p38 inhibitors served as a starting point for the design of JNK3 inhibitors. Construction of a 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole scaffold led to the synthesis of the (S)-enantiomers, which exhibited p38/JNK3 IC50 ratio of up to 10 and were up to 20 times more potent inhibitors of JNK3 than the relevant (R)-enantiomers. The JNK3 inhibitory potency correlated well with inhibition of c-Jun phosphorylation and neuroprotective properties of the compounds in low K+-induced cell death of rat cerebellar granule neurotics. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.076
• 作为产物：
  描述：

  (R)-(-)-5-羟甲基-2-吡咯烷酮 在 劳森试剂 、 咪唑 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.33h， 生成 (R)-5-(tert-butyldiphenylsiloxy)methylpyrrolidin-2-thione
  参考文献：
  名称：

  Synthesis, Chemical Reactivity, and Cytotoxicity of 2-Bis(alkoxycarbonyl)methyliden-1-azabicyclo[3.1.0]hexane Systems Related to Antitumor Antibiotic Carzinophilin A

  摘要：

  以(S)-焦谷氨酸和(R)-焦谷氨酸为起点，合成了标题化合物的对映体。研究发现，它们易受氮丙啶分子的亲核开环作用影响，体外细胞毒性较弱。

  DOI：

  10.1246/cl.1992.975

文献信息

• Synthetic studies of carzinophilin. Part 1: Synthesis of 2-methylidene-1-azabicyclo[3.1.0]hexane systems related to carzinophilin
  作者：Masaru Hashimoto、Miyoko Matsumoto、Shiro Terashima

  DOI：10.1016/s0040-4020(03)00377-6

  日期：2003.4

  Synthesis of the model compounds of carzinophilin carrying 2-methylidene-1-aza-bicyclo[3.1.0]hexane systems was achieved. Formation of malonylidenes or N-acyl-glycinylidenepyrrolidines was carried out by utilizing Eschenmoser's sulfide contraction or Herdeis's condensation between the 2-methylthio-Δ1-pyrrolone derivatives and ethyl nitroacetate, respectively. The 1-azabicyclo-[3.1.0]hexane systems

  合成了带有2-亚甲基-1-氮杂-双环[3.1.0]己烷体系的卡那菲林模型化合物。malonylidenes或形成ñ酰基-glycinylidenepyrrolidines通过利用Eschenmoser的硫化物的收缩或Herdeis的2-甲硫-Δ之间的缩合进行1个分别-pyrrolone衍生物和硝基乙酸乙酯。1-氮杂双环-[3.1.0]己烷体系是通过碱促进的氮丙啶形成而构建的。
• Synthesis, Chemical Reactivity, and Cytotoxicity of 2-Bis(alkoxycarbonyl)methyliden-1-azabicyclo[3.1.0]hexane Systems Related to Antitumor Antibiotic Carzinophilin A
  作者：Masaru Hashimoto、Kaoru Yamada、Shiro Terashima

  DOI：10.1246/cl.1992.975

  日期：1992.6

  Enantiomeric pairs of the title compounds were synthesized starting from (S)-and (R)-pyroglutamic acid. They were found to be susceptible to nucleophilic ring opening of aziridine moieties and to exhibit weak in vitro cytotoxicity.

  以(S)-焦谷氨酸和(R)-焦谷氨酸为起点，合成了标题化合物的对映体。研究发现，它们易受氮丙啶分子的亲核开环作用影响，体外细胞毒性较弱。
• The neuroprotective action of JNK3 inhibitors based on the 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole scaffold
  作者：Piotr P. Graczyk、Afzal Khan、Gurpreet S. Bhatia、Vanessa Palmer、Darren Medland、Hirotoshi Numata、Hitoshi Oinuma、Jacqueline Catchick、Angela Dunne、Moira Ellis、Caroline Smales、Jonathan Whitfield、Stephen J. Neame、Bina Shah、Daniel Wilton、Louise Morgan、Toshal Patel、Raymond Chung、Howard Desmond、James M. Staddon、Nobuaki Sato、Atsushi Inoue

  DOI：10.1016/j.bmcl.2005.07.076

  日期：2005.11

  Imidazole-based structures of p38 inhibitors served as a starting point for the design of JNK3 inhibitors. Construction of a 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole scaffold led to the synthesis of the (S)-enantiomers, which exhibited p38/JNK3 IC50 ratio of up to 10 and were up to 20 times more potent inhibitors of JNK3 than the relevant (R)-enantiomers. The JNK3 inhibitory potency correlated well with inhibition of c-Jun phosphorylation and neuroprotective properties of the compounds in low K+-induced cell death of rat cerebellar granule neurotics. (c) 2005 Elsevier Ltd. All rights reserved.