2-(β-cyanoethyl)-4,4,6-trimethyl-tetrahydro-(2H)-1,3-oxazine | 292041-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-(β-cyanoethyl)-4,4,6-trimethyl-tetrahydro-(2H)-1,3-oxazine
• 英文别名: 3-(4,4,6-Trimethyl-1,3-oxazinan-2-yl)propanenitrile
• CAS: 292041-48-6
• 化学式: C₁₀H₁₈N₂O
• 分子量: 182.266
• InChiKey: MJSPJCAFXITHJS-UHFFFAOYSA-N

物化性质

• 沸点：
  294.2±25.0 °C(Predicted)
• 密度：
  0.914±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl N-benzyl-L-tryptophanate 、 2-(β-cyanoethyl)-4,4,6-trimethyl-tetrahydro-(2H)-1,3-oxazine 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 30.0h， 生成 cis-methyl 1-(β-cyanoethyl)-N_b-benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate 、 trans-methyl 1-(β-cyanoethyl)-N_b-benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Pictet–Spengler reaction: is carbonyl the best choice? A highly diastereoselective alternative approach to trans-1,3-disubstituted tetrahydro-β-carbolines

  摘要：

  Unprecedented 1,2,3-trisubstituted tetrahydro-beta-carbolines (THBCs) have been synthesized via a short and highly diastereoselective synthetic route. The key step of the sequence is a flexible variant of the Pictet-Spengler reaction employing synthetic equivalents of several non-available carbonyl compounds. Using one such synthon, the resultant THBC could be further ring-closed to a tetracyclic indole alkaloidal skeleton. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00751-6
• 作为产物：
  描述：

  2-甲基-2,4-戊二醇 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2-(β-cyanoethyl)-4,4,6-trimethyl-tetrahydro-(2H)-1,3-oxazine
  参考文献：
  名称：

  Pictet–Spengler reaction: is carbonyl the best choice? A highly diastereoselective alternative approach to trans-1,3-disubstituted tetrahydro-β-carbolines

  摘要：

  Unprecedented 1,2,3-trisubstituted tetrahydro-beta-carbolines (THBCs) have been synthesized via a short and highly diastereoselective synthetic route. The key step of the sequence is a flexible variant of the Pictet-Spengler reaction employing synthetic equivalents of several non-available carbonyl compounds. Using one such synthon, the resultant THBC could be further ring-closed to a tetracyclic indole alkaloidal skeleton. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00751-6

文献信息

• Modified Pictet–Spengler reaction. A highly diastereoselective approach to 1,2,3-trisubstituted-1,2,3,4-tetrahydro-β-carbolines using perhydro-1,3-heterocycles
  作者：Kamaljit Singh、Prasant K Deb、P Venugopalan

  DOI：10.1016/s0040-4020(01)00763-3

  日期：2001.9

  A flexible variant of the Pictet-Spengler reaction employing oxazinanes as synthetic equivalents of several carbonyl compounds has been developed. Using acid catalyzed one pot condensation of perhydro-1,3-heterocycles various 1,3-disubstituted and 1,2,3-trisubstituted-1,2,3,4-tetrahydro-beta -carbolines (THBCs) have been synthesized diastereoselectively. (C) 2001 Elsevier Science Ltd. All rights reserved.