2-(β-cyanoethyl)-4,4,6-trimethyl-5,6-dihydro-(4H)-1,3-oxazine | 99167-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-(β-cyanoethyl)-4,4,6-trimethyl-5,6-dihydro-(4H)-1,3-oxazine
• 英文别名: 3-(4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-propionitrile；3-(4,4,6-Trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-propionitril；4.4.6-Trimethyl-2-<2-cyan-aethyl>-Δ¹-dihydro-1.3-oxazin；2-(β-Cyanaethyl)-4.4.6-trimethyl-5.6-dihydro-1.3-oxazin；3-(4,4,6-trimethyl-5,6-dihydro-1,3-oxazin-2-yl)propanenitrile
• CAS: 99167-22-3
• 化学式: C₁₀H₁₆N₂O
• 分子量: 180.25
• InChiKey: NLVNRTLXOALJMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  45.38
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(β-cyanoethyl)-4,4,6-trimethyl-5,6-dihydro-(4H)-1,3-oxazine 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
• 作为产物：
  描述：

  2-甲基-2,4-戊二醇 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 生成 2-(β-cyanoethyl)-4,4,6-trimethyl-5,6-dihydro-(4H)-1,3-oxazine
  参考文献：
  名称：

  Notes- The Structure of the Addition Product from Hydrogen Cyanide and a 2-Vinyldihydro-1,3-oxazine

  摘要：

  DOI：

  10.1021/jo01071a609

文献信息

• 2-Alkenyl-4,4,6-trimethyl-5,6-dihydro-1,3-oxazines
  作者：John Lynn

  DOI：10.1021/jo01087a613

  日期：1959.5
• 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.