(S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methylsulfanyl-3,4-dihydro-2H-pyrrole | 852674-75-0

• 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: (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methylsulfanyl-3,4-dihydro-2H-pyrrole
• 英文别名: tert-butyl-[[(2S)-5-methylsulfanyl-3,4-dihydro-2H-pyrrol-2-yl]methoxy]-diphenylsilane
• CAS: 852674-75-0
• 化学式: C₂₂H₂₉NOSSi
• 分子量: 383.63
• InChiKey: VSVZRJGNIXSFHM-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methylsulfanyl-3,4-dihydro-2H-pyrrole 在 sodium hydroxide 、 四丁基氟化铵 、 氢溴酸 、 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 、 乙酸乙酯 为溶剂， 反应 38.0h， 生成 (5S)-2-(4-fluorophenyl)-5-[(4-methoxyphenyl)methoxymethyl]-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole
  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：

  (5S)-5-[[[叔丁基二苯基硅基]氧]甲基]-2-吡咯烷酮 在 劳森试剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methylsulfanyl-3,4-dihydro-2H-pyrrole
  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

文献信息

• An <i>N</i>-Acyliminium Cyclization Approach to a Total Synthesis of (+)-Cylindricine C
  作者：Jia Liu、Jacob J. Swidorski、Scott D. Peters、Richard P. Hsung

  DOI：10.1021/jo0501846

  日期：2005.5.1

  the development of an enantioselective total synthesis of (+)-cylindricine C are described here. The total synthesis itself was accomplished in 8 steps, featuring an N-acyliminium cyclization strategy, the seldom-used Wharton rearrangement, and a key epimerization at C5.

  在此描述在开发（+）-cylindricine C的对映选择性全合成过程中遇到的问题和解决方案的详细信息。总的合成本身以8个步骤完成，具有N-酰基环化策略，很少使用的沃顿重排以及C5上的关键差向异构化。
• Annulation of Thioimidates and Vinyl Carbodiimides to Prepare 2-Aminopyrimidines, Competent Nucleophiles for Intramolecular Alkyne Hydroamination. Synthesis of (−)-Crambidine
  作者：Nicholas R. Perl、Nathan D. Ide、Sudeep Prajapati、Hahdi H. Perfect、Sergio G. Durón、David Y. Gin

  DOI：10.1021/ja910831k

  日期：2010.2.17

  A convergent synthesis of(-)-crambidine is reported. The sequence Capitalizes on two novel key transformations, including.(I) a [4+2] annulation of thioimidates with vinyl carbodiimides and an alkyne hydroamination employing 2-aminopyrimidine nucleophiles.
• 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.