Ethyl 3-oxo-4-(3,4,4-trimethyl-1,3-oxazolidin-2-yl)butanoate | 184955-25-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: Ethyl 3-oxo-4-(3,4,4-trimethyl-1,3-oxazolidin-2-yl)butanoate
• CAS: 184955-25-7
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: UTXBFKYPGBQXHB-UHFFFAOYSA-N

物化性质

• 沸点：
  308.7±32.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 3-oxo-4-(3,4,4-trimethyl-1,3-oxazolidin-2-yl)butanoate 在 盐酸 作用下， 以 乙醇 、 溶剂黄146 、 乙腈 为溶剂， 生成 1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolidine-2,4-dione
  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 Ethyl 3-oxo-4-(3,4,4-trimethyl-1,3-oxazolidin-2-yl)butanoate
  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

• A synthetic entry into fused pyran derivatives through carbon transfer reactions of 1,3-oxazinanes and oxazolidines with carbon nucleophiles
  作者：Kamaljit Singh、Jasbir Singh、Harjit Singh

  DOI：10.1016/0040-4020(96)00879-4

  日期：1996.11

  of various 2 substituted 1,3-oxazinanes 3 and 1,3-oxazolidines 4 with cyclic carbon nucleophiles viz. 5,5-dimethyl-1,3-cyclohexanedione and 1,3-cyclohexanedione furnish xanthene derivatives, whereas a Knoevenagel reaction proceeds with acyclic nucleophiles. In case of 4b and 4c, a unique synthesis of functionalised α-tetralones has emerged. Reactions of mixtures of cyclic and acyclic carbon nucleophiles

  各种2个取代的1,3-恶嗪并3和1,3-恶唑烷4与环状碳亲核试剂的酸催化缩合。5,5-二甲基-1,3-环己二酮和1,3-环己二酮提供了x吨衍生物，而Knoevenagel反应则与无环亲核试剂一起进行。在4b和4c的情况下，出现了功能化的α-四氢萘酮的独特合成。环状和无环碳亲核试剂与3的混合物的反应提供了一些官能化的且部分还原的苯并吡喃衍生物。
• 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.