1-(1-selenoxo-4-pentenyl)pyrrolidine | 209978-95-0

• 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: 1-(1-selenoxo-4-pentenyl)pyrrolidine
• 英文别名: 1-Pyrrolidin-1-ylpent-4-ene-1-selone
• CAS: 209978-95-0
• 化学式: C₉H₁₅NSe
• 分子量: 216.185
• InChiKey: CINQYDSGQXBMRF-UHFFFAOYSA-N

物化性质

• 沸点：
  258.9±33.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1-selenoxo-4-pentenyl)pyrrolidine 在 氧化环己烯 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.67h， 生成
  参考文献：
  名称：

  Reaction of lithium eneselenolates derived from selenoamides with ketones: a highly diastereoselective synthetic route to β,β-disubstituted β-hydroxy selenoamides

  摘要：

  The reaction of lithium eneselenolates generated from selenoamides with a variety of ketones proceeded smoothly at -78degreesC to give the corresponding beta,beta-disubstituted beta-hydroxy selenoamides in moderate to good yields. The reaction showed high diastereoselectivity. The products obtained were converted to the corresponding amides by reacting them with cyclohexene oxide. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02877-0
• 作为产物：
  描述：

  1-(1-selenoxo-2-trimethylsilyl-4-pentenyl)pyrrolidine 在 四丁基氟化铵 作用下， 以87%的产率得到1-(1-selenoxo-4-pentenyl)pyrrolidine
  参考文献：
  名称：

  4-戊烯硒酰胺的高效合成方法：末端乙炔、硒、胺和烯丙基溴的四组分偶联反应

  摘要：

  由末端乙炔、丁基锂和硒生成的烷基烯醇酸锂与胺和烯丙基溴在 67°C 下在 THF 中顺利进行反应，以中等至高产率得到 4-戊烯硒酰胺。该反应可以通过带有烯丙基基团的硒烯中间体进行，然后是胺的攻击以得到产物。脂肪族和芳香族乙炔、甲硅烷基乙炔和烯炔用作末端乙炔。一摩尔量的仲胺是有效的，而过量的伯胺是必要的。与 2-丁烯基溴的反应表现出高区域选择性，尽管它们产生立体异构混合物。炔丙醇的甲硅烷基醚反应生成α,β-不饱和硒酰胺作为产物。

  DOI：

  10.1246/bcsj.71.1193

文献信息

• Sequential Addition Reactions of Lithium Acetylides and Grignard Reagents to Selenoiminium Salts Leading to 2-Propynyl Tertiary Amines Bearing a Tetrasubstituted Carbon Center
  作者：Toshiaki Murai、Sho Nogawa、Yuichiro Mutoh

  DOI：10.1246/bcsj.80.2220

  日期：2007.11.15

  Selenoiminium salts generated in situ from selenoamides and MeOTf were reacted sequentially with lithium acetylides and Grignard reagents to give 2-propynyl tertiary amines bearing a tetrasubstitut...

  由硒酰胺和 MeOTf 原位生成的硒亚胺盐依次与乙炔锂和格氏试剂反应，得到带有四取代基的 2-丙炔基叔胺。
• Reactions of Lithium Eneselenolates of Selenoamides with Carbonyl Compounds
  作者：Toshiaki Murai、Akiko Suzuki、Mai Takagi、Shinzi Kato

  DOI：10.1080/10426500108046640

  日期：2001.5

  Abstract The reaction of lithium eneselenolates and dieneselenolates derived form selenoamides with a variety of carbonyl compounds has been described. In the reaction with α,β-unsaturated esters and ketones Michael addition reaction took place very rapidly, whereas the reaction with α,β-unsaturated aldehydes gave selectively 1,2-adducts. As for the reaction of lithium dieneselenolates ally1 group

  摘要 已经描述了由硒酰胺衍生的烯醇酸锂和二烯醇酸锂与多种羰基化合物的反应。在与α,β-不饱和酯和酮的反应中，迈克尔加成反应发生得非常迅速，而与α,β-不饱和醛的反应则选择性地生成1,2-加合物。至于二烯醇锂的反应，烯丙基和醛被选择性地引入到硒羰基的α位。
• Aldol-type condensation reactions of lithium eneselenolates generated from selenoamides with aldehydes
  作者：Toshiaki Murai、Akiko Suzuki、Shinzi Kato

  DOI：10.1039/b100198l

  日期：2001.10.11

  Aldol-type condensation reactions of α-monosubstituted selenoamides with a variety of aldehydes are examined to furnish β-hydroxy selenoamides in good to high yields. The use of selenoamides derived from dibenzylamine exhibits high stereoselectivity. As for the reaction with aliphatic aldehydes selenoamides show better yields and selectivity compared with ordinary amides. Conversion of the resulting β-hydroxy selenoamides to 1,3-amino alcohols is also described.

  研究了 α-单取代硒酰胺与多种醛的醛醇型缩合反应，从而以良好到较高的收率制备出 β-羟基硒酰胺。使用二苄胺衍生的硒酰胺具有很高的立体选择性。与普通酰胺相比，硒酰胺与脂肪醛的反应具有更好的产率和选择性。此外，还介绍了将β-羟基硒酰胺转化为 1,3-氨基醇的情况。
• An Efficient Synthetic Method of 4-Penteneselenoamides: Four-Component Coupling Reaction of Terminal Acetylenes, Selenium, Amines, and Allylic Bromides
  作者：Toshiaki Murai、Tatsuya Ezaka、Shinzi Kato

  DOI：10.1246/bcsj.71.1193

  日期：1998.5

  The reaction of lithium alkyneselenolates generated from terminal acetylenes, butyllithium, and selenium with amines and allylic bromides proceeded smoothly in THF at 67 °C to give 4-penteneselenoamides in moderate to high yields. The reaction may proceed via selenoketene intermediates bearing an allylic group, followed by the attack of amines to give the products. Aliphatic and aromatic acetylenes

  由末端乙炔、丁基锂和硒生成的烷基烯醇酸锂与胺和烯丙基溴在 67°C 下在 THF 中顺利进行反应，以中等至高产率得到 4-戊烯硒酰胺。该反应可以通过带有烯丙基基团的硒烯中间体进行，然后是胺的攻击以得到产物。脂肪族和芳香族乙炔、甲硅烷基乙炔和烯炔用作末端乙炔。一摩尔量的仲胺是有效的，而过量的伯胺是必要的。与 2-丁烯基溴的反应表现出高区域选择性，尽管它们产生立体异构混合物。炔丙醇的甲硅烷基醚反应生成α,β-不饱和硒酰胺作为产物。
• Reaction of lithium eneselenolates derived from selenoamides with ketones: a highly diastereoselective synthetic route to β,β-disubstituted β-hydroxy selenoamides
  作者：Toshiaki Murai、Masato Ishizuka、Akiko Suzuki、Shinzi Kato

  DOI：10.1016/s0040-4039(02)02877-0

  日期：2003.2

  The reaction of lithium eneselenolates generated from selenoamides with a variety of ketones proceeded smoothly at -78degreesC to give the corresponding beta,beta-disubstituted beta-hydroxy selenoamides in moderate to good yields. The reaction showed high diastereoselectivity. The products obtained were converted to the corresponding amides by reacting them with cyclohexene oxide. (C) 2003 Elsevier Science Ltd. All rights reserved.