4-(tert-butylthio)but-2-ynal | 1189110-55-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(tert-butylthio)but-2-ynal
• 英文别名: 4-Tert-butylsulfanylbut-2-ynal
• CAS: 1189110-55-1
• 化学式: C₈H₁₂OS
• 分子量: 156.249
• InChiKey: SIKHMDOGDBQGIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(tert-butylthio)but-2-ynal 、 (4bR,7R,8aR)-9-(4-methoxybenzyl)-7-(methylthio)-6-(((triethylsilyl)oxy)methyl)-7,8-dihydro-9H-8a,4b-(epiminoethano)carbazole 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.12h， 以96%的产率得到[(1R,9R,11S)-16-(4-tert-butylsulfanylbut-2-ynyl)-8-[(4-methoxyphenyl)methyl]-11-methylsulfanyl-8,16-diazatetracyclo[7.4.3.01,9.02,7]hexadeca-2,4,6,12-tetraen-12-yl]methoxy-triethylsilane
  参考文献：
  名称：

  Nine-Step Enantioselective Total Synthesis of (+)-Minfiensine

  摘要：

  An enantioselective total synthesis of the Strychnos alkaloid (+)-minfiensine has been accomplished. Prominent features of this synthesis include (i) a new enantioselective organocatalytic Diels-Alder/amine cyclization sequence to build the central tetracyclic pyrroloindoline framework in four steps from commercial materials and (ii) a 6-exo-dig radical cyclization to forge the final piperidinyl ring system. This total synthesis of (+)-minfiensine was completed in nine chemical steps and 21% overall yield.

  DOI：

  10.1021/ja906472m
• 作为产物：
  描述：

  4-(tert-butylthio)but-2-yn-1-ol 在 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以452 mg的产率得到4-(tert-butylthio)but-2-ynal
  参考文献：
  名称：

  Nine-Step Enantioselective Total Synthesis of (+)-Minfiensine

  摘要：

  An enantioselective total synthesis of the Strychnos alkaloid (+)-minfiensine has been accomplished. Prominent features of this synthesis include (i) a new enantioselective organocatalytic Diels-Alder/amine cyclization sequence to build the central tetracyclic pyrroloindoline framework in four steps from commercial materials and (ii) a 6-exo-dig radical cyclization to forge the final piperidinyl ring system. This total synthesis of (+)-minfiensine was completed in nine chemical steps and 21% overall yield.

  DOI：

  10.1021/ja906472m

文献信息

• Nine-Step Enantioselective Total Synthesis of (−)-Vincorine
  作者：Benjamin D. Horning、David W. C. MacMillan

  DOI：10.1021/ja402933s

  日期：2013.5.1

  highly enantioselective total synthesis of the akuammiline alkaloid (-)-vincorine has been accomplished. A key element of the synthesis is a stereoselective organocatalytic Diels-Alder, iminium cyclization cascade sequence, which serves to construct the tetracyclic alkaloid core architecture in one step from simple achiral precursors. The challenging seven-membered azepanyl ring system is installed by way

  已经完成了 akuammiline 生物碱 (-)-vincorine 的简洁且高度对映选择性的全合成。该合成的一个关键要素是立体选择性有机催化 Diels-Alder、亚胺鎓环化级联序列，其用于从简单的非手性前体一步构建四环生物碱核心结构。具有挑战性的七元氮杂环系统是通过从酰基碲化物前体引发的单个电子介导的环化事件安装的。(-)-vincorine 的全合成是通过 9 个步骤和 9% 的总产率从市售起始材料中实现的。
• Nine-Step Enantioselective Total Synthesis of (+)-Minfiensine
  作者：Spencer B. Jones、Bryon Simmons、David W. C. MacMillan

  DOI：10.1021/ja906472m

  日期：2009.9.30

  An enantioselective total synthesis of the Strychnos alkaloid (+)-minfiensine has been accomplished. Prominent features of this synthesis include (i) a new enantioselective organocatalytic Diels-Alder/amine cyclization sequence to build the central tetracyclic pyrroloindoline framework in four steps from commercial materials and (ii) a 6-exo-dig radical cyclization to forge the final piperidinyl ring system. This total synthesis of (+)-minfiensine was completed in nine chemical steps and 21% overall yield.