(1E)-oct-1-en-1-yl phenyl selenone | 1203602-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1E)-oct-1-en-1-yl phenyl selenone
• 英文别名: [(1E)-oct-1-en-1-ylselenonyl]benzene；(E)-oct-1-en-yl phenyl selenone；[(E)-oct-1-enyl]selenonylbenzene
• CAS: 1203602-50-9
• 化学式: C₁₄H₂₀O₂Se
• 分子量: 299.272
• InChiKey: QVQVPSIAKVWBOE-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1E)-oct-1-en-1-yl phenyl selenone 、 ethyl 2-cyano-2-(4-methoxyphenyl)acetate 在 C₂₉H₃₀F₆N₄O₂ 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  通过有机催化迈克尔加成到乙烯基硒酮上的一种新的立体选择性合成含季立体中心的环丙烷的方法

  摘要：

  报道了一种新型的有机催化方法，用于立体选择性合成高度取代的环丙烷。通过将α-取代的氰基乙酸酯加到由双官能尿素催化剂催化的易于获得的乙烯基硒酮中生成的迈克尔加合物，通过由脱乙氧基羰基化过程诱导的分子内烷基化而平滑地环化。的单釜序列生成环丙烷轴承相邻的叔和季立体中心为单Ž -异构体在较高产率和良好的对映体过量。

  DOI：

  10.1002/adsc.200900222
• 作为产物：
  描述：

  (E)-1-phenylseleno-1-octene 在 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以77%的产率得到(1E)-oct-1-en-1-yl phenyl selenone
  参考文献：
  名称：

  Preparation of both enantiomers of cyclopropane derivatives from the reaction of vinyl selenones with di-(−)-bornyl malonate

  摘要：

  The reaction of vinyl selenones with di-(-)-bornyl malonate and sodium hydride occurred with low diastereoselectivity and afforded a mixture of two diastereomeric cyclopropane derivatives in comparable yields. These, however, could be easily separated by chromatography. Removal of the bornyl group afforded highly enantiomerically enriched cyclopropanes. An example of the simple conversions of these cyclopropanes into useful cyclopropane alpha-amino acids is also illustrated. The syntheses of several vinyl selenides and selenones are also described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.05.019

文献信息

• One-pot synthesis of aziridines from vinyl selenones and variously functionalized primary amines
  作者：Silvia Sternativo、Francesca Marini、Francesca Del Verme、Antonella Calandriello、Lorenzo Testaferri、Marcello Tiecco

  DOI：10.1016/j.tet.2010.06.055

  日期：2010.8

  Variously substituted aziridines were conveniently prepared by an aza-Michael Initiated Ring Closure (aza-MIRC) reaction starting from vinyl selenones and primary amines, aminoalcohols or diamines. The reactions proceed in very high yields at room temperature in toluene or water. A significant rate acceleration was observed under aqueous conditions.

  各种取代的氮丙啶可方便地通过aza-Michael引发的闭环（aza-MIRC）反应从乙烯基硒酮和伯胺，氨基醇或二胺开始制备。反应在室温下在甲苯或水中以非常高的产率进行。在水性条件下观察到明显的速率加速。
• Oxone-Mediated Oxidation of Vinyl Selenides in Water
  作者：Martina Palomba、Francesco Trappetti、Luana Bagnoli、Claudio Santi、Francesca Marini

  DOI：10.1002/ejoc.201800498

  日期：2018.8.7

  A simple and practical procedure for the oxidation of vinyl selenides to the corresponding selenones using Oxone in water at 60 °C has been reported.

  据报道，在60°C的水中使用Oxone可以简单，实用的方法将乙烯基硒化物氧化为相应的硒酮。
• Preparation of both enantiomers of cyclopropane derivatives from the reaction of vinyl selenones with di-(−)-bornyl malonate
  作者：Luana Bagnoli、Catalina Scarponi、Lorenzo Testaferri、Marcello Tiecco

  DOI：10.1016/j.tetasy.2009.05.019

  日期：2009.7

  The reaction of vinyl selenones with di-(-)-bornyl malonate and sodium hydride occurred with low diastereoselectivity and afforded a mixture of two diastereomeric cyclopropane derivatives in comparable yields. These, however, could be easily separated by chromatography. Removal of the bornyl group afforded highly enantiomerically enriched cyclopropanes. An example of the simple conversions of these cyclopropanes into useful cyclopropane alpha-amino acids is also illustrated. The syntheses of several vinyl selenides and selenones are also described. (C) 2009 Elsevier Ltd. All rights reserved.
• A New Stereoselective Synthesis of Cyclopropanes Containing Quaternary Stereocentres via Organocatalytic Michael Addition to Vinyl Selenones
  作者：Francesca Marini、Silvia Sternativo、Francesca Del Verme、Lorenzo Testaferri、Marcello Tiecco

  DOI：10.1002/adsc.200900222

  日期：——

  organocatalytic method for the stereoselective synthesis of highly substituted cyclopropanes is reported. The Michael adducts, generated through the addition of α-substituted cyanoacetates to easily accessible vinyl selenones catalyzed by a bifunctional ureidic catalyst, smoothly cyclize by intramolecular alkylation induced by a de-ethoxycarbonylation process. The one-pot sequence generates cyclopropanes

  报道了一种新型的有机催化方法，用于立体选择性合成高度取代的环丙烷。通过将α-取代的氰基乙酸酯加到由双官能尿素催化剂催化的易于获得的乙烯基硒酮中生成的迈克尔加合物，通过由脱乙氧基羰基化过程诱导的分子内烷基化而平滑地环化。的单釜序列生成环丙烷轴承相邻的叔和季立体中心为单Ž -异构体在较高产率和良好的对映体过量。