tert-butyl 3-methyl-2-oxo-3-(phenylselanyl)-1-pyrrolidinecarboxylate | 171017-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl 3-methyl-2-oxo-3-(phenylselanyl)-1-pyrrolidinecarboxylate
• 英文别名: 1-tert-butoxycarbonyl-3-methyl-3-phenylselenyl-2-pyrrolidinone；Tert-butyl 3-methyl-2-oxo-3-phenylselanylpyrrolidine-1-carboxylate
• CAS: 171017-19-9
• 化学式: C₁₆H₂₁NO₃Se
• 分子量: 354.308
• InChiKey: PHZLUASVLFGVRA-UHFFFAOYSA-N

物化性质

• 熔点：
  86-88 °C
• 沸点：
  459.9±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-methyl-2-oxo-3-(phenylselanyl)-1-pyrrolidinecarboxylate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 溶剂黄146 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 4.5h， 生成 (1-tert-butoxycarbonyl-3-methyl-3-pyrrolin)-5-yl-phosphonic acid diethyl ester
  参考文献：
  名称：

  Total Synthesis of (+)-Ampullicin and (+)-Isoampullicin:  Two Fungal Metabolites with Growth Regulatory Activity Isolated from Ampulliferina Sp. 27

  摘要：

  The total synthesis of the growth regulators (+)-ampullicin 1 and (+)-isoampullicin 2 from (R)(-)-carvone 5 was accomplished by application of an 18-step sequence with 4.5% overall yield. The crucial step of the synthetic strategy lies on the internal displacement of tosylate 13 by means of the lactone enolate. In this way, access was opened to the tricyclic core present in these biologically active sesquiterpenic amides. A Horner-Emmons reaction between the carbaldehyde 16 and the phosphonate 22 led us to the stereoselective preparation of (+)-ampullicin 1. Standard transformation of I into the thermodynamically more stable geometric isomer (+)-isoampullicin 2 was trivial. The absolute configuration of both amides was established by X-ray analysis of a sample of synthetic (+)-isoampullicin 2.

  DOI：

  10.1021/jo010527+
• 作为产物：
  描述：

  3-甲基-2-吡咯烷酮 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl 3-methyl-2-oxo-3-(phenylselanyl)-1-pyrrolidinecarboxylate
  参考文献：
  名称：

  分子内环化N-酰基亚胺离子的分子内环化反应，合成α，β-不饱和螺内酰胺。

  摘要：

  （±）-6-苄基-3-甲基-3-en-1,6-二氮杂螺[4.5]癸烷-2,7-二酮（18）（（±）-pandamarine的螺部分）的合成已实现（15a）和（15b）的5-（N-苄基-4-羧酰胺基丁烯基）-3-甲基-3-en-pvrrolin-2-one的（Z）和（E）异构体的氧化环化。还讨论了两种丁烯前体在分子内环化中显示的立体选择性。

  DOI：

  10.1016/0040-4039(95)01568-3

文献信息

• Synthesis of α,β-unsaturated spirolactams by intramolecular cyclization of endocyclic N-Acyliminium ions.
  作者：Maria J. Martín、Francisco Bermejo

  DOI：10.1016/0040-4039(95)01568-3

  日期：1995.10

  The synthesis of (±)-6-benzyl-3-methyl-3-en-1,6-diazaspiro[4.5]decane-2,7-dione (18), the spiro moiety of (±)-pandamarine has been achieved by oxidative cyclization of the (Z) and (E) isomers of 5-(N-benzyl-4-carboxamido-butylidene)-3-methyl-3-en-pvrrolin-2-one (15a) and (15b). The stereoselectivity exhibited in the intramolecular cyclization by both butylidene precursors has also been discussed.

  （±）-6-苄基-3-甲基-3-en-1,6-二氮杂螺[4.5]癸烷-2,7-二酮（18）（（±）-pandamarine的螺部分）的合成已实现（15a）和（15b）的5-（N-苄基-4-羧酰胺基丁烯基）-3-甲基-3-en-pvrrolin-2-one的（Z）和（E）异构体的氧化环化。还讨论了两种丁烯前体在分子内环化中显示的立体选择性。
• Aglairubine—discrepancies during the course of structure elucidation
  作者：Richard Detterbeck、Manfred Hesse

  DOI：10.1016/s0040-4039(02)00869-9

  日期：2002.5

  A short synthesis of the originally proposed structure 1 for the putrescine alkaloid aglairubine is presented as well as for a conceivable structure alternative 11. Due to the ascertained mismatch of spectroscopical data for synthetic and natural compounds, the published aglairubine structure has to be revised. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Total Synthesis of (+)-Ampullicin and (+)-Isoampullicin:  Two Fungal Metabolites with Growth Regulatory Activity Isolated from <i>Ampulliferina</i> Sp. 27
  作者：Francisco A. Bermejo、Rosario Rico-Ferreira、S. Bamidele-Sanni、Santiago García-Granda

  DOI：10.1021/jo010527+

  日期：2001.12.1

  The total synthesis of the growth regulators (+)-ampullicin 1 and (+)-isoampullicin 2 from (R)(-)-carvone 5 was accomplished by application of an 18-step sequence with 4.5% overall yield. The crucial step of the synthetic strategy lies on the internal displacement of tosylate 13 by means of the lactone enolate. In this way, access was opened to the tricyclic core present in these biologically active sesquiterpenic amides. A Horner-Emmons reaction between the carbaldehyde 16 and the phosphonate 22 led us to the stereoselective preparation of (+)-ampullicin 1. Standard transformation of I into the thermodynamically more stable geometric isomer (+)-isoampullicin 2 was trivial. The absolute configuration of both amides was established by X-ray analysis of a sample of synthetic (+)-isoampullicin 2.