2-(7-Bromo-heptyl)-2-ethyl-[1,3]dioxolane | 155505-91-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(7-Bromo-heptyl)-2-ethyl-[1,3]dioxolane
• 英文别名: 2-(7-Bromoheptyl)-2-ethyl-1,3-dioxolane
• CAS: 155505-91-2
• 化学式: C₁₂H₂₃BrO₂
• 分子量: 279.217
• InChiKey: FSWSERHVCFBXAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  312.2±17.0 °C(predicted)
• 密度：
  1.162±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(7-Bromo-heptyl)-2-ethyl-[1,3]dioxolane 在 palladium on activated charcoal 盐酸 、 正丁基锂 、 氢气 、 三苯基膦 作用下， 以 乙醇 、 水 为溶剂， 生成 12-[(2R,5R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-1-(toluene-4-sulfonyl)-piperidin-2-yl]-dodecan-3-one
  参考文献：
  名称：

  Asymmetric total synthesis of (−)-prosophylline

  摘要：

  The asymmetric total synthesis of (-)-prosophylline from D-glucal via (2S)-hydroxymethyl-dihydropyridone 6 by a 17-step synthesis and 12% overall yield is presented. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01387-8
• 作为产物：
  描述：

  8-溴-1-辛醇 在 硫酸 、 pyridinium chlorochromate 作用下， 生成 2-(7-Bromo-heptyl)-2-ethyl-[1,3]dioxolane
  参考文献：
  名称：

  氮杂-环化反应是羟基化生物碱脂质的一种途径。（±）-脯氨酸的合成

  摘要：

  描述了（±）-propinpinine的总合成。使用氮杂环化法生成六元氮杂环，通过使用δ-内酰胺模板实现立体化学控制，内酰胺的同系物在哌啶环上引入了烷基链取代基。

  DOI：

  10.1016/0040-4039(94)88315-7

文献信息

• Glycolactam compounds, process for preparation and uses thereof
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US10774043B2

  公开（公告）日：2020-09-15

  The present invention discloses compounds of Formula I, wherein each of R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from H, OBn, OH, CH2OBn, CH2OH, CH3; R9 is selected from alkyl, substituted alkyl, hydroxyl alkyl, alkenyl, benzyl; process for preparation of N-alkylated glycolactam compounds of Formula I and their use for the synthesis of piperidine alkaloids and their analogues.

  本发明公开了式 I 的化合物、 其中R1、R2、R3、R4、R5、R6、R7和R8各自独立地选自H、OBn、OH、CH2OBn、CH2OH、CH3；R9选自烷基、取代烷基、羟基烷基、烯基、苄基；式I的N-烷基化糖内酰胺化合物的制备工艺及其用于合成哌啶生物碱及其类似物的工艺。
• Construction of Hydroxylated Alkaloids (.+-.)-Mannonolactam, (.+-.)-Deoxymannojirimycin, and (.+-.)-Prosopinine through Aza-Annulation
  作者：Gregory R. Cook、Lars G. Beholz、John R. Stille

  DOI：10.1021/jo00092a015

  日期：1994.7

  The aza-annulation of beta enamino carbonyl substrates with acrylate derivatives provides an efficient and convenient route for the regioselective construction of delta-lactams. This two-step ring-forming sequence involved initial generation of the benzyl enamine through either a condensation or conjugate addition reaction with BnNH(2), followed by aza-annulation with acryloyl chloride or acrylic anhydride. Controlled by the rigid framework of the intermediate lactam, introduction of ring substituents was accomplished with high relative stereoselectivity. The carbonyl functionality, which was necessary to direct the regioselectivity of the aza-annulation reaction, was then transformed into a protected hydroxyl substituent through Baeyer-Villiger oxidation. The resultant delta-lactam product was used as a valuable intermediate in the synthesis of three natural products. Subsequent modification of this delta-lactam gave the naturally occurring alpha-mannosidase inhibitors (+/-)-mannonolactam and (+/-)deoxymannojirimycin, while synthesis of the alkaloid (+/-)-prosopinine was accomplished through homologation of the lactam carbonyl.
• GLYCOLACTAM COMPOUNDS, PROCESS FOR PREPARATION AND USES THEREOF
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US20190194133A1

  公开（公告）日：2019-06-27

  The present invention discloses compounds of Formula I, Wherein, R 1 ═R 2 ═R 3 ═R 4 ═R 5 ═R 6 ═R 7 ═R 8 and is selected from H, OBn, OH, CH 2 OH, CH 2 OH, CH 3 ; R 9 is selected front alkyl, substituted alkyl, hydroxyl alkyl, alkenyl, benzyl; process for preparation of N-alkylated glycolactain compounds of Formula I and their use for the synthesis of piperidine alkaloids and their analogues.
• [EN] GLYCOLACTAM COMPOUNDS, PROCESS FOR PREPARATION AND USES THEREOF<br/>[FR] COMPOSÉS GLYCOLACTAME, PROCÉDÉ POUR LEUR PRÉPARATION ET UTILISATIONS ASSOCIÉES
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2017191657A1

  公开（公告）日：2017-11-09

  The present invention discloses compounds of Formula I, Wherein, R1 = R2 = R3 = R4 = R5 = R6 = R7 = R8 and is selected from H, OBn, OH, CH2OBn, CH2OH, CH3; R9 is selected from alkyl, substituted alkyl, hydroxyl alkyl, alkenyl, benzyl; process for preparation of N-alkylated glycolactam compounds of Formula I and their use for the synthesis of piperidine alkaloids and their analogues.