(Ss,3S)-(+)-N-(tert-butylsulfinyl)-3-amino-5-(2-methyl-1,3-dioxolan-2-yl)pentanal | 1360562-74-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Ss,3S)-(+)-N-(tert-butylsulfinyl)-3-amino-5-(2-methyl-1,3-dioxolan-2-yl)pentanal
• 英文别名: (S)-2-methyl-N-[(3S)-1-(2-methyl-1,3-dioxolan-2-yl)-5-oxopentan-3-yl]propane-2-sulfinamide
• CAS: 1360562-74-8
• 化学式: C₁₃H₂₅NO₄S
• 分子量: 291.412
• InChiKey: VTAKWCXUQCNISP-WLRWDXFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  83.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Ss,3S)-(+)-N-(tert-butylsulfinyl)-3-amino-5-(2-methyl-1,3-dioxolan-2-yl)pentanal 在 盐酸 、 过氧化脲素 、 甲基三氧化铼(VII) 、 aluminum tri-tert-butoxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 133.0h， 生成 (-)-methyl (1S,2R,3R,6S)-3-methyl-7-aza-8-oxatricyclo[4.2.1.0(3,7)]-nonane-2-carboxylate
  参考文献：
  名称：

  Enantioselective Synthesis of Cocaine C-1 Analogues using Sulfinimines (N-Sulfinyl Imines)

  摘要：

  The first examples of cocaine analogues having substituents (methyl, ethyl, n-propyl, n-pentyl, and phenyl) at the C-1 position of the cocaine tropane skeleton were prepared by heating sulfinimine-derived alpha,beta-unsaturated pyrrolidine nitrones. In the presence of the Lewis acid Al((OBu)-Bu-t)(3) the nitrones undergo an intramolecular [3 + 2] cycloaddition to give tricyclic isoxazolidines that were transformed in three steps to the cocaine analogues. In the absence of the Lewis acid, lactams were formed resulting from rearrangement of the nitrone to an oxaziridine. A novel Pd-and base-promoted rearrangement of methanesulfonate salts of isoxazolidine to bridge bicyclic[4.2.1]isoxazolidines was discovered.

  DOI：

  10.1021/jo202652f
• 作为产物：
  描述：

  3-(2-甲基-1,3-二氧戊环-2-基)丙醛 在 titanium(IV) tetraethanolate 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 27.17h， 生成 (Ss,3S)-(+)-N-(tert-butylsulfinyl)-3-amino-5-(2-methyl-1,3-dioxolan-2-yl)pentanal
  参考文献：
  名称：

  Enantioselective Synthesis of Cocaine C-1 Analogues using Sulfinimines (N-Sulfinyl Imines)

  摘要：

  The first examples of cocaine analogues having substituents (methyl, ethyl, n-propyl, n-pentyl, and phenyl) at the C-1 position of the cocaine tropane skeleton were prepared by heating sulfinimine-derived alpha,beta-unsaturated pyrrolidine nitrones. In the presence of the Lewis acid Al((OBu)-Bu-t)(3) the nitrones undergo an intramolecular [3 + 2] cycloaddition to give tricyclic isoxazolidines that were transformed in three steps to the cocaine analogues. In the absence of the Lewis acid, lactams were formed resulting from rearrangement of the nitrone to an oxaziridine. A novel Pd-and base-promoted rearrangement of methanesulfonate salts of isoxazolidine to bridge bicyclic[4.2.1]isoxazolidines was discovered.

  DOI：

  10.1021/jo202652f

文献信息

• [EN] COCAINE ANALOGS AND METHODS OF PREPARATION AND USES THEREOF<br/>[FR] ANALOGUES DE COCAÏNE ET LEURS PROCÉDÉS DE PRÉPARATION ET D'UTILISATION
  申请人：UNIV TEMPLE

  公开号：WO2012009263A1

  公开（公告）日：2012-01-19

  The invention provides novel cocaine analogs. The invention also provides a method of preparing cocaine analogs with control over the substituents installed at the C-1, C-2, C-3, C-4 and N-8 positions of the tropane bicyclic scaffold. The invention further provides a method of providing anesthesia to a subject in need thereof comprising administering to the subject a pharmaceutical composition comprising a compound of the invention. The invention also provides a method of blocking reuptake of a monoamine neurotransmitter in a subject in need thereof, to a subject in need thereof comprising administering to the subject a pharmaceutical composition comprising a compound of the invention.

  该发明提供了新型可卡因类似物。该发明还提供了一种制备可卡因类似物的方法，该方法可以控制在Tropane双环支架的C-1、C-2、C-3、C-4和N-8位置安装的取代基。该发明还提供了一种给需要麻醉的受试者提供麻醉的方法，包括向受试者注射包含该发明化合物的药物组合物。该发明还提供了一种阻止需要单胺神经递质再摄取的受试者的方法，包括向受试者注射包含该发明化合物的药物组合物。
• Enantioselective Synthesis of Cocaine C-1 Analogues using Sulfinimines (<i>N</i>-Sulfinyl Imines)
  作者：Franklin A. Davis、Narendra V. Gaddiraju、Naresh Theddu、Joshua R. Hummel、Sandeep K. Kondaveeti、Michael J. Zdilla

  DOI：10.1021/jo202652f

  日期：2012.3.2

  The first examples of cocaine analogues having substituents (methyl, ethyl, n-propyl, n-pentyl, and phenyl) at the C-1 position of the cocaine tropane skeleton were prepared by heating sulfinimine-derived alpha,beta-unsaturated pyrrolidine nitrones. In the presence of the Lewis acid Al((OBu)-Bu-t)(3) the nitrones undergo an intramolecular [3 + 2] cycloaddition to give tricyclic isoxazolidines that were transformed in three steps to the cocaine analogues. In the absence of the Lewis acid, lactams were formed resulting from rearrangement of the nitrone to an oxaziridine. A novel Pd-and base-promoted rearrangement of methanesulfonate salts of isoxazolidine to bridge bicyclic[4.2.1]isoxazolidines was discovered.