(S)-(4-cyclopropyl-1-isopropyl-2-oxo-but-3-ynyl)-carbamic acid tert-butyl ester | 1414917-88-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-(4-cyclopropyl-1-isopropyl-2-oxo-but-3-ynyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(3S)-6-cyclopropyl-2-methyl-4-oxohex-5-yn-3-yl]carbamate
• CAS: 1414917-88-6
• 化学式: C₁₅H₂₃NO₃
• 分子量: 265.353
• InChiKey: YQOBYLAOENWGAU-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(4-cyclopropyl-1-isopropyl-2-oxo-but-3-ynyl)-carbamic acid tert-butyl ester 在 potassium carbonate 、 platinum(II) chloride 作用下， 反应 0.5h， 以98%的产率得到5-cyclopropyl-2-isopropyl-3-oxo-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Pyrrolin-4-ones by Pt-Catalyzed Cycloisomerization in PEG under Microwaves

  摘要：

  The unprecedented eco-friendly Pt-catalyzed 5-endo-dig cycloisomerization of readily available a-amino ynones is reported under microwave irradiation in PEG-3400 as reaction matrix. The corresponding pure pyrrolin-4-ones were obtained in excellent yields (80-98%) directly after a straightforward precipitation-filtration workup, thus avoiding any chromatographic purification. The catalytic system was recycled and the chiral purity of all the products was also investigated.

  DOI：

  10.1021/jo302474r
• 作为产物：
  描述：

  环丙乙炔 、 2-甲基-2-丙基(4S)-4-异丙基-2,5-二氧代-1,3-恶唑烷-3-羧酸酯 在 正丁基锂 、 lithium bromide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.5h， 以94%的产率得到(S)-(4-cyclopropyl-1-isopropyl-2-oxo-but-3-ynyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Preparation of enantioenriched iodinated pyrrolinones by iodocyclization of α-amino-ynones

  摘要：

  前所未有的电亲核碘介导的α-氨基-炔酮环化反应在温和条件下以优异的产率获得了对映体富集的β-碘吡咯林-4-酮。起始的取代α-氨基-炔酮是通过对光学纯的氨基酸N保护的羧酸酸酐（UNCA）选择性单加成有机锂化合物获得的。

  DOI：

  10.1039/c2ob26427g

文献信息

• Preparation of enantioenriched iodinated pyrrolinones by iodocyclization of α-amino-ynones
  作者：Rosella Spina、Evelina Colacino、Bartolo Gabriele、Giuseppe Salerno、Jean Martinez、Frédéric Lamaty

  DOI：10.1039/c2ob26427g

  日期：——

  The unprecedented electrophilic iodo-mediated cyclization of α-amino-ynones afforded enantiomerically enriched β-iodopyrrolin-4-ones in excellent yields under mild conditions. The starting substituted α-amino-ynones were obtained from the chiral pool by selective mono-addition of an organolithium to optically pure N-protected carboxyanhydrides of amino acids (UNCAs).

  前所未有的电亲核碘介导的α-氨基-炔酮环化反应在温和条件下以优异的产率获得了对映体富集的β-碘吡咯林-4-酮。起始的取代α-氨基-炔酮是通过对光学纯的氨基酸N保护的羧酸酸酐（UNCA）选择性单加成有机锂化合物获得的。
• Synthesis of Pyrrolin-4-ones by Pt-Catalyzed Cycloisomerization in PEG under Microwaves
  作者：Rosella Spina、Evelina Colacino、Bartolo Gabriele、Giuseppe Salerno、Jean Martinez、Frédéric Lamaty

  DOI：10.1021/jo302474r

  日期：2013.3.15

  The unprecedented eco-friendly Pt-catalyzed 5-endo-dig cycloisomerization of readily available a-amino ynones is reported under microwave irradiation in PEG-3400 as reaction matrix. The corresponding pure pyrrolin-4-ones were obtained in excellent yields (80-98%) directly after a straightforward precipitation-filtration workup, thus avoiding any chromatographic purification. The catalytic system was recycled and the chiral purity of all the products was also investigated.