(R)-(-)-2-(4-toluenesulfonyloxy)-phenylacetic acid methyl ester | 131981-95-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-(-)-2-(4-toluenesulfonyloxy)-phenylacetic acid methyl ester
• 英文别名: methyl (R)-2-phenyl-2-p-toluenesulfonyloxyacetate；(S)-2-(4-toluenesulfonyloxy)phenylacetic acid methyl ester；methyl (2R)-2-(4-methylphenyl)sulfonyloxy-2-phenylacetate
• CAS: 131981-95-8
• 化学式: C₁₆H₁₆O₅S
• 分子量: 320.366
• InChiKey: AMIOLNZOZKCJKW-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-(4-toluenesulfonyloxy)-phenylacetic acid methyl ester 在 sodium ethanolate 、 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 5.17h， 生成 (4R,8aS)-4-phenyl-perhydropyrrolo[1,2-a]pyrazine-1,3-dione
  参考文献：
  名称：

  The synthesis of new diastereomers of (4S,8aS)- and (4R,8aS)-4-phenyl-perhydropyrrole[1,2-a]pyrazine-1,3-dione

  摘要：

  The synthesis of new (4S,8aS)- and (4R,8aS)-4-phenyl-perhydropyrrole[1,2-a]pyrazine-1,3-diones in the cyclocondensation reaction of the respective derivatives of L-prolineamide is described. The effect of the amount of NaOEt, temperature, and reaction time on the proportions of diastereomers formed in the cyclocondensation reaction was examined. The structures of the diastercomers were confirmed by GC/MS, FIRMS, HPLC; XRD, and H-1 and C-13 NMR investigations. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.08.025
• 作为产物：
  描述：

  (R)-(-)-扁桃酸甲酯 、 对甲苯磺酰氯 在 silver(l) oxide 作用下， 以67%的产率得到(R)-(-)-2-(4-toluenesulfonyloxy)-phenylacetic acid methyl ester
  参考文献：
  名称：

  手性硫代甲基酮与适当的有机金属的反应中的非对面分化

  摘要：

  发现将硫原子而不是氧气引入酮的α位对于有效的非对面分化至关重要。即，可以通过有机金属与衍生自（S）-2-巯基-2-苯基乙醇和α-卤代酮的手性硫代甲基酮的反应获得任何一种叔醇的非对映异构体。例如，从将MeLi攻击SI面取向，而我2的Zn优选重新-facial攻击。另外，利用本方法成功地合成了1，2 - O-异亚丙基-2-甲基-1,2,5-戊三醇的两种对映异构体，所述对映体是合成额叶磷脂的关键中间体。

  DOI：

  10.1016/s0040-4039(00)97877-8

文献信息

• Synthesis and anticonvulsant activity of novel 2,6-diketopiperazine derivatives. Part 1: Perhydropyrrole[1,2-a]pyrazines
  作者：Maciej Dawidowski、Franciszek Herold、Andrzej Chodkowski、Jerzy Kleps、Paweł Szulczyk、Marcin Wilczek

  DOI：10.1016/j.ejmech.2011.07.027

  日期：2011.10

  A number of novel pyrrole[1,2-a]pyrazine derivatives were synthesized and evaluated in in vivo animal models of epilepsy. Among them, several compounds displayed promising seizure protection in the maximal electroshock seizure (MES), subcutaneous metrazol seizure (scMET), 6 Hz and pilocarpine-induced status prevention (PISP) tests, with ED50 values comparable to the reference anticonvulsant drugs (AEDs)

  合成了许多新颖的吡咯[1,2- a ]吡嗪衍生物，并在癫痫的体内动物模型中进行了评估。其中，几种化合物在最大电击惊厥（MES），皮下甲硝唑惊厥（scMET），6 Hz和毛果芸香碱引起的状态预防（PISP）测试中显示出有希望的癫痫保护作用，其ED 50值可与参考抗惊厥药（AEDs）相提并论。 ）。观察到吡咯[1,2- a ]吡嗪核心的立体化学和构象偏好对体内药理活性的关键影响。合成药物的抗惊厥作用机制很可能不是通过抑制电压依赖性钠（Na+）电流。
• 含哌嗪结构化合物在制备LSD1抑制剂中的应 用
  申请人：福建金乐医药科技有限公司

  公开号：CN107174584B

  公开（公告）日：2020-09-01

  本发明公开了一种含有哌嗪结构的化合物在制备组蛋白赖氨酸特异性去甲基化酶（LSD1）抑制剂中的应用，该化合物的结构通式为（其中，A为氢、羰基或硫代羰基）或其构型异构体、药用盐；或为或其药用盐。该化合物对LSD1具有明显抑制作用，可制备成LSD1抑制剂，用于与组蛋白特异性去甲基化酶活性相关的疾病预防和治疗。
• Either diastereofacial differentiation in the reaction of chiral thiomethylketones with appropriate organometallics
  作者：Tamotsu Fujisawa、Isao Takemura、Yutaka Ukaji

  DOI：10.1016/s0040-4039(00)97877-8

  日期：1990.1

  of sulfur atom instead of oxygen into α-position to ketone was found to be crucial for efficient diastereofacial differentiation; i.e., either diastereomer of tertiary alcohol could be obtained by the reaction of organometallics to chiral thiomethylketones derived from (S)-2-mercapto-2-phenylethanol and α-halo ketones. For example, MeLi attacked from si-face, while Me2Zn preferred re-facial attack. In

  发现将硫原子而不是氧气引入酮的α位对于有效的非对面分化至关重要。即，可以通过有机金属与衍生自（S）-2-巯基-2-苯基乙醇和α-卤代酮的手性硫代甲基酮的反应获得任何一种叔醇的非对映异构体。例如，从将MeLi攻击SI面取向，而我2的Zn优选重新-facial攻击。另外，利用本方法成功地合成了1，2 - O-异亚丙基-2-甲基-1,2,5-戊三醇的两种对映异构体，所述对映体是合成额叶磷脂的关键中间体。
• The synthesis and conformational analysis of optical isomers of 4-phenyl-perhydropyrido[1,2-a]pyrazine-1,3-dione: an example of ‘solid state–frozen’ dynamics in nitrogen-bridged bicyclic 2,6-diketopiperazines
  作者：Maciej Dawidowski、Franciszek Herold、Marcin Wilczek、Jerzy Kleps、Irena Wolska、Jadwiga Turło、Andrzej Chodkowski、Paweł Widomski、Anna Bielejewska

  DOI：10.1016/j.tetasy.2009.06.022

  日期：2009.8

  The synthesis, chemical properties, and conformational analysis of enantiopure (4R,9aS)-, (4S,9aR)-, (4S,9aS)-, and (4R,9aR)-4-phenyl-perhydropyrido[1,2-a]pyrazine-1,3-diones having potential biological activity are described. An interesting example of the coexistence of two invertomers of the (4R,9aR)-diastereomer in a single crystal unit cell is reported. The invertomers differ in the cis/trans-relationship between the fused rings and in the absolute configuration at the chiral nitrogen atom. The structure and equilibrium distributions of the respective conformers have been determined by NMR spectroscopy in both polar and non-polar solvents at various temperatures. The NMR spectra show that dynamic processes in the imide parts of the interconverting species are restrained by self-aggregation. The (4S,9aR)-diastereomer exists in a single conformation with insignificant dynamic effects. (c) 2009 Elsevier Ltd. All rights reserved.
• The synthesis of new diastereomers of (4S,8aS)- and (4R,8aS)-4-phenyl-perhydropyrrole[1,2-a]pyrazine-1,3-dione
  作者：Franciszek Herold、Maciej Dawidowski、Irena Wolska、Andrzej Chodkowski、Jerzy Kleps、Jadwiga Turło、Andrzej Zimniak

  DOI：10.1016/j.tetasy.2007.08.025

  日期：2007.9

  The synthesis of new (4S,8aS)- and (4R,8aS)-4-phenyl-perhydropyrrole[1,2-a]pyrazine-1,3-diones in the cyclocondensation reaction of the respective derivatives of L-prolineamide is described. The effect of the amount of NaOEt, temperature, and reaction time on the proportions of diastereomers formed in the cyclocondensation reaction was examined. The structures of the diastercomers were confirmed by GC/MS, FIRMS, HPLC; XRD, and H-1 and C-13 NMR investigations. (C) 2007 Elsevier Ltd. All rights reserved.