(2S)-2-[1-phenyl-2-(phenylseleno)ethoxy]propanal | 944125-05-7

• 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: (2S)-2-[1-phenyl-2-(phenylseleno)ethoxy]propanal
• 英文别名: (2S)-2-(1-phenyl-2-phenylselanylethoxy)propanal
• CAS: 944125-05-7
• 化学式: C₁₇H₁₈O₂Se
• 分子量: 333.289
• InChiKey: BEDSBEDXBMURDJ-MBIQTGHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-[1-phenyl-2-(phenylseleno)ethoxy]propanal 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 2.0h， 以38%的产率得到3-ethoxy-3-phenylpropanal
  参考文献：
  名称：

  Intramolecular addition of carbon radicals to aldehydes: synthesis of enantiopure tetrahydrofuran-3-ols

  摘要：

  A simple and efficient substrate-controlled asymmetric synthesis of enantiopure tetrahydrofuran-3-ols by a 5-exo-trig radical cyclization is described. This cyclization occurs when a delta-carbon radical adds intramolecularly to the carbonyl group of an aldehyde. The delta-carbon radicals can be efficiently produced from the tin hydride mediated deselenenylation of 5-phenylseleno-3-oxapentanals, which were easily prepared starting from commercially available enantiopure epoxides or chlorohydrins. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.047
• 作为产物：
  描述：

  苯基硒基三氟甲烷磺酸酯 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.5h， 生成 (2S)-2-[1-phenyl-2-(phenylseleno)ethoxy]propanal
  参考文献：
  名称：

  Intramolecular addition of carbon radicals to aldehydes: synthesis of enantiopure tetrahydrofuran-3-ols

  摘要：

  A simple and efficient substrate-controlled asymmetric synthesis of enantiopure tetrahydrofuran-3-ols by a 5-exo-trig radical cyclization is described. This cyclization occurs when a delta-carbon radical adds intramolecularly to the carbonyl group of an aldehyde. The delta-carbon radicals can be efficiently produced from the tin hydride mediated deselenenylation of 5-phenylseleno-3-oxapentanals, which were easily prepared starting from commercially available enantiopure epoxides or chlorohydrins. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.047

文献信息

• Intramolecular addition of carbon radicals to aldehydes: synthesis of enantiopure tetrahydrofuran-3-ols
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Silvia Sternativo、Claudio Santi、Luana Bagnoli、Andrea Temperini

  DOI：10.1016/j.tet.2007.04.047

  日期：2007.6

  A simple and efficient substrate-controlled asymmetric synthesis of enantiopure tetrahydrofuran-3-ols by a 5-exo-trig radical cyclization is described. This cyclization occurs when a delta-carbon radical adds intramolecularly to the carbonyl group of an aldehyde. The delta-carbon radicals can be efficiently produced from the tin hydride mediated deselenenylation of 5-phenylseleno-3-oxapentanals, which were easily prepared starting from commercially available enantiopure epoxides or chlorohydrins. (c) 2007 Elsevier Ltd. All rights reserved.