2-cyanomethyl-3,4,4-trimethyl-oxazolidine | 182363-02-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2-cyanomethyl-3,4,4-trimethyl-oxazolidine
• 英文别名: 2-cyanomethyl-3,4,4-trimethyloxazolidine；2-(3,4,4-Trimethyl-1,3-oxazolidin-2-yl)acetonitrile
• CAS: 182363-02-6
• 化学式: C₈H₁₄N₂O
• 分子量: 154.212
• InChiKey: LPPDPCHSPBIXOL-UHFFFAOYSA-N

物化性质

• 沸点：
  239.3±20.0 °C(Predicted)
• 密度：
  0.962±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl N-benzyl-L-tryptophanate 、 2-cyanomethyl-3,4,4-trimethyl-oxazolidine 在 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 cis-methyl 1-cyanomethyl-N_b-benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate 、 trans-methyl 1-cyanomethyl-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：

  4,4-二甲基-2-氧唑啉 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 2-cyanomethyl-3,4,4-trimethyl-oxazolidine
  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

• An expedient protocol of the Biginelli dihydropyrimidine synthesis using carbonyl equivalents
  作者：Kamaljit Singh、Jasbir Singh、Prasant K. Deb、Harjit Singh

  DOI：10.1016/s0040-4020(99)00760-7

  日期：1999.10

  A one - pot condensation of perhydro-1,3 heterocycles - aldehyde equivalents with ethyl acetoacetate and ureas provides a convenient synthesis of the title compounds with a variety of substituents at C-4. Yields are equivalent or significantly higher than the conventional methods.

  全氢-1,3杂环-醛当量与乙酰乙酸乙酯和脲的一锅缩合反应可方便地合成标题化合物，其在C-4处具有多个取代基。产率与常规方法相当或相当高。
• Efficient and versatile single pot approach to dipyrromethanes and bis(heterocyclyl)methanes
  作者：Kamaljit Singh、Sonia Behal、Maninder Singh Hundal

  DOI：10.1016/j.tet.2005.04.029

  日期：2005.7

  An efficient single pot route is presented involving the use of 0, N-perhydro 1,3-heterocycles as carbonyl equivalents for the synthesis of 5-substituted dipyrromethanes, 5,10-disubstituted tripyrranes and bis(heterocyclyl)methanes. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.
• Pictet–Spengler reaction: is carbonyl the best choice? A highly diastereoselective alternative approach to trans-1,3-disubstituted tetrahydro-β-carbolines
  作者：Kamaljit Singh、Prasant K Deb

  DOI：10.1016/s0040-4039(00)00751-6

  日期：2000.6

  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.