(?)-薄荷基(S)-1-[(R)-alpha-甲基苄基]氮丙啶-2-羧酸酯 | 397849-97-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (?)-薄荷基(S)-1-[(R)-alpha-甲基苄基]氮丙啶-2-羧酸酯
• 中文别名: （-）-甲基（S）-1-[（R）-α-甲基苄基]氮丙啶-2-羧酸酯
• 英文名称: N-[(R)-(+)-α-methylbenzyl]-2(S)-carboxylic acid (-)-menthol ester
• 英文别名: N-(R)-α-methylbenzylaziridine-2(S)-carboxylic acid menthyl ester；(2S)-1-[(1R)-1-phenylethyl]-2-aziridine carboxylic acid (-)-menthol ester；[(1R,2S,5R)-5-Methyl-2-propan-2-ylcyclohexyl] (2S)-1-[(1R)-1-phenylethyl]aziridine-2-carboxylate
• CAS: 397849-97-7
• 化学式: C₂₁H₃₁NO₂
• 分子量: 329.483
• InChiKey: BLLGOPLLCDRJQD-OOYAWMOSSA-N

物化性质

• 熔点：
  68-72°C (lit.)
• 沸点：
  398.7±35.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (?)-薄荷基(S)-1-[(R)-alpha-甲基苄基]氮丙啶-2-羧酸酯 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 2(S)-{N-[(R)-α-methylbenzyl]amino}-3-O-acetyl-1,1-diphenyl-1,3-propanediol
  参考文献：
  名称：

  Chang, Jae-Won; Ha, Hyun-Joon; Park, Chan Sun, Heterocycles, 2002, vol. 57, # 6, p. 1143 - 1148

  摘要：

  DOI：

文献信息

• Lewis acid-catalyzed stereospecific ring expansion of aziridine-2-carboxylates to imidazolidin-2-ones
  作者：Min Sung Kim、Yong-Woo Kim、Heung Sik Hahm、Jae Won Jang、Won Koo Lee、Hyun-Joon Ha

  DOI：10.1039/b503750f

  日期：——

  Lewis acid-catalyzed ring expansion reaction of chiral aziridine-2-carboxylate proceeds regio- and stereospecifically to yield enantiomerically pure 4-functionalized imidazolidin-2-ones in high yields.

  路易斯酸催化的手性氮丙啶-2-羧酸手性环扩环反应在区域和立体上进行，以高收率产生对映体纯的4-官能化的咪唑烷基-2-酮。
• [EN] SPHINGOLIPID DERIVATIVES AND THE COMPOSITION FOR ANTI-CANCER CONTAINING THE SAME<br/>[FR] DERIVES DE SPHINGOLIPIDES ET COMPOSITION ANTICANCEREUSE CONTENANT LESDITS DERIVES
  申请人：DOOSAN CORP

  公开号：WO2006004359A1

  公开（公告）日：2006-01-12

  Disclosed are a novel sphingolipid derivative having a sphingosine kinase suppressing activity and a composition containing the same. When the newly synthesized sphingolipid derivative of the invention is used, it is possible to maintain concentrations of ceramide and sphingosine to be high by preventing ceramide and sphingosine from being phosphorylated due to sphingosine kinase since an activity of sphingosine kinase is suppressed. In addition, since the apoptosis is induced in a cancer cell by ceramide and sphingosine, it is possible to treat or prevent a cancer or disease related to the cancer. Further, it is possible to treat or prevent a hyper- proliferative disease such as cancer or proliferation-promoting activity of sphingosine kinase. Accordingly, the composition containing the same can be used as a composition for suppressing sphingosine kinase and a composition for treating or preventing a cancer or hyper-proliferative disease.

  本发明揭示了一种具有抑制鞘氨醇激酶活性的新型鞘脂类衍生物以及含有该衍生物的组合物。当使用本发明中新合成的鞘脂类衍生物时，通过抑制鞘氨醇激酶的活性，可以使神经酰胺和鞘氨醇的浓度保持较高水平，从而防止由于鞘氨醇激酶导致神经酰胺和鞘氨醇被磷酸化。此外，由于神经酰胺和鞘氨醇可以在癌细胞中诱导凋亡，因此可以治疗或预防与癌症相关的癌症或疾病。此外，可以治疗或预防癌症或增殖促进活性的鞘氨醇激酶等高增殖性疾病。因此，含有该衍生物的组合物可用作抑制鞘氨醇激酶的组合物以及用于治疗或预防癌症或高增殖性疾病的组合物。
• Structure and conserved function of iso-branched sphingoid bases from the nematode Caenorhabditis elegans
  作者：J. Thomas Hannich、Denia Mellal、Suihan Feng、Andreas Zumbuehl、Howard Riezman

  DOI：10.1039/c6sc04831e

  日期：——

  Nematode-specific iso-branched sphingoid base synthesis: drug-target against parasites and genetic model system for human diseases.

  线虫特异性异支链鞘氨醇基合成：寄生虫药物靶点和人类疾病遗传模型系统。
• A formal synthesis of (−)-swainsonine from a chiral aziridine
  作者：Hwan Geun Choi、Ji Hye Kwon、Jong Chan Kim、Won Koo Lee、Heesung Eum、Hyun-Joon Ha

  DOI：10.1016/j.tetlet.2010.04.069

  日期：2010.6

  A formal synthesis of enantiomerically pure (-)-swainsonine was successfully achieved using intramolecular cyclization of the amino alcohol 4 which was derived from a readily available 1-(R)-alpha-methylbenzylaziridine-2-carboxylic acid (-)-menthol ester 6. (C) 2010 Elsevier Ltd. All rights reserved.
• A Novel Synthesis of 5-Functionalized Oxazolidin-2-ones from Enantiomerically Pure 2-Substituted <i>N</i>-[(<i>R</i>)-(+)-α-Methylbenzyl]aziridines
  作者：Tae Bo Sim、Se Hun Kang、Kun Su Lee、Won Koo Lee、Hoseop Yun、Yongkwan Dong、Hyun-Joon Ha

  DOI：10.1021/jo0261911

  日期：2003.1.1

  5-Funtionalized enantiomerically pure oxazolidin-2-ones were prepared in one pot from commercially available chiral aziridines bearing an electron-withdrawing group at C-2 with retention of the configuration in high yields by regioselective aziridine ring-opening followed by intramolecular cyclization.