(R)-3-(N,N-dibenzylamino)-1-pentanol

• 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)-3-(N,N-dibenzylamino)-1-pentanol
• 英文别名: (3R)-3-(dibenzylamino)pentan-1-ol
• 化学式: C₁₉H₂₅NO
• 分子量: 283.414
• InChiKey: AYJLHJHBUPAYIE-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-戊烯-1-醇 在 4-二甲氨基吡啶 、 (S)-(+)-5,5'-双[二(3,5-二叔丁基-4-甲氧基苯基)膦]-4,4'-二-1,3-苯并二氧戊环 、 diethoxymethylsilane 、 (triphenylphosphine)copper(I) hydride hexamer 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 98.0h， 生成 (R)-3-(N,N-dibenzylamino)-1-pentanol
  参考文献：
  名称：

  未活化内部烯烃的区域选择性，不对称形式加氢胺化

  摘要：

  我们报告了由DTBM-SEGPHOS连接的铜催化剂催化的不对称内部烯烃的区域选择性和对映体选择性加氢胺化反应。反应的区域选择性由在均烯丙基位置的醚，酯和磺酰胺基团的电子效应控制。观察到的选择性强调了远程取代基的感应作用对在烃基上发生的催化过程的选择性的影响，该方法可直接获得各种具有高对映选择性的1,3-氨基醇衍生物。

  DOI：

  10.1002/anie.201509235

文献信息

• Practical EPC synthesis of 1,2- and 1,3-amino alcohols
  作者：Peter Gmeiner、Annerose Kärtner、Dagmar Junge

  DOI：10.1016/s0040-4039(00)79340-3

  日期：1993.7

  An efficient synthesis of enantiomerically pure 1,2- and 1,3-amino alcohols (4,10) through the key intermediates 2 and 8a,b, obtained from L-aspartic acid, is reported. Using 4d as an example it is shown that the products can serve as precursors for unusual amino aldehydes and nonproteinogenic amino acids.

  据报道，通过从L-天冬氨酸获得的关键中间体2和8a，b有效合成了对映体纯的1，2-和1，3-氨基醇（4，10）。以4d为例，表明该产品可以用作不寻常的氨基醛和非蛋白氨基酸的前体。
• Enantiomerically Pure Amino Alcohols and Diamino Alcohols from L-Aspartic Acid. Application to the Synthesis of Epi- and Diepislaframine
  作者：Peter Gmeiner、Dagmar Junge、Annerose Kaertner

  DOI：10.1021/jo00101a042

  日期：1994.11

  Starting from natural aspartic acid (6) a practical method for the synthesis of enantiomerically pure 3-amino alcohols 8 including 3,4-diamino derivatives is described. After perbenzylation of 6 and reduction of both carboxylates, position 4 of the resultant (dibenzylamino)butanediol (11) could be regioselectively blocked to afford the silyloxy-protected intermediate 12a. Functionalization of position 1 was accomplished by nucleophilic displacement reactions including a 2-fold migration of the dibenzylamino substituent or by reductive amination of the amino aldehyde 15. Both routes proceeded under complete preservation of the optical purity. For envisioned SAR studies, we, furthermore, report on the application of this method to a chirospecific synthesis of epi- and diepislaframine (9a and 9b) as diastereomers of the highly bioactive indolizidine alkaloid slaframine (9c). Our first approach including reductive coupling of the chiral amino aldehyde 15 with 5-hydroxypyrrolidine failed when formation of a quaternary ammonium salt occurred, preventing the anticipated anionic cyclization. Therefore, we turned out attention to methodology developed by Wasserman. In fact, introduction of a 3-hydroxypyrrole-2-carboxylate fragment gave a cyclization precursor (30b) which could be successfully transformed into epi- and diepislaframine.