2-hexylsulfanyl-propionaldahyde

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-hexylsulfanyl-propionaldahyde
• 英文别名: α-hexylthiopropanal；2-(Hexylthio)propanal；2-hexylsulfanylpropanal
• 化学式: C₉H₁₈OS
• 分子量: 174.307
• InChiKey: AFQCTTFBZPGLJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  11.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  四溴化碳 、 2-hexylsulfanyl-propionaldahyde 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以94%的产率得到1,1-dibromo-3-pentylsulfanyl-but-1-ene
  参考文献：
  名称：

  通过亚磺酰亚胺[2,3]-适体重排的对映体的对映体选择性合成。

  摘要：

  通过炔丙基硫酰亚胺的[2,3]-σ重排，制备具有高水平对映体纯度的手性烯丙酰胺。所需的支链炔丙基硫化物是通过对映选择性有机催化醛α-亚磺酰基化，然后进行Corey-Fuchs炔基化反应制得的。

  DOI：

  10.1021/ol900146s
• 作为产物：
  描述：

  2-Hexylthio-propionsaeureethylester 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以96%的产率得到2-hexylsulfanyl-propionaldahyde
  参考文献：
  名称：

  通过亚磺酰亚胺[2,3]-适体重排的对映体的对映体选择性合成。

  摘要：

  通过炔丙基硫酰亚胺的[2,3]-σ重排，制备具有高水平对映体纯度的手性烯丙酰胺。所需的支链炔丙基硫化物是通过对映选择性有机催化醛α-亚磺酰基化，然后进行Corey-Fuchs炔基化反应制得的。

  DOI：

  10.1021/ol900146s

文献信息

• Regiospecific conversion of alkenyl sulphides to α-sulphenylated carbonyl compounds by oxygenation in the presence of thiophenol
  作者：Jun-ichi Yoshida、Shogo Nakatani、Sachihiko Isoe

  DOI：10.1039/c39880001468

  日期：——

  Regiospecific conversion of alkenyl sulphides to α-sulphenylated carbonyl compounds was achieved by oxygenation in the presence of thiophenol; electrolysis was found to be quite effective for initiation of the reaction.

  在硫酚的存在下，通过氧化实现烯基硫的区域特异性转化为α-磺苯基化的羰基化合物。发现电解对于引发反应是非常有效的。
• Enantioselective Synthesis of α-Aminophosphonates via Organocatalytic Sulfenylation and [2,3]-Sigmatropic Sulfimide Rearrangement
  作者：Alan Armstrong、Neil Deacon、Craig Donald

  DOI：10.1055/s-0030-1260309

  日期：2011.10

  γ-Unsaturated-α-aminophosphonates are prepared in enantiomerically enriched form via organocatalytic aldehyde α-sulfenylation/olefination followed by oxaziridine-mediated sulfimidation and sulfimide [2,3]-sigmatropic rearrangement. Subsequent N-deprotection and amino acid coupling are also accomplished. asymmetric catalysis - amination - rearrangement - organocatalysis - oxaziridine

  β，γ-不饱和-α-氨基膦酸酯的制备是通过有机催化醛α-亚磺酰基化/烯烃化，然后恶唑烷介导的磺酰亚胺化和磺酰亚胺[2,3]-σ重排而以对映体富集的形式进行。随后的N-脱保护和氨基酸偶联也完成了。 不对称催化-胺化-重排-有机催化-恶唑烷
• Electroinitiated oxygenation of alkenyl sulfides and alkynes in the presence of thiophenol
  作者：Junichi Yoshida、Shogo Nakatani、Sachihiko Isoe

  DOI：10.1021/jo00070a021

  日期：1993.8

  Electrolysis of alkenyl sulfides in the presence of thiophenol with bubbling of molecular oxygen gave the corresponding alpha-(phenylthio) carbonyl compounds with the consumption of a catalytic amount of electricity. An electroinitiated radical chain mechanism has been proposed. The reaction also took place without electrochemical initiation, but much (5-50 times) longer reaction time was required for the completion of the reaction. The potential utility of the present reaction in organic synthesis is demonstrated by the net 1,2-transposition of a phenylthio group and a carbonyl group. The electroinitiated oxygenation of ketene dithioacetals also proceeded smoothly to give the corresponding alpha-(phenylthio) thiol esters. It was also found that the electroinitiated oxygenation of alkynes in the presence of thiophenol gave alpha-(phenylthio) carbonyl compounds. A mechanism involving the initial formation of alkenyl sulfides has been proposed.
• Enantioselective Synthesis of Allenamides via Sulfimide [2,3]-Sigmatropic Rearrangement
  作者：Alan Armstrong、Daniel P. G. Emmerson

  DOI：10.1021/ol900146s

  日期：2009.4.2

  Chiral allenamides are prepared with high levels of enantiomeric purity by [2,3]-sigmatropic rearrangement of propargylic sulfimides. The required branched propargylic sulfides are prepared by an enantioselective organocatalytic aldehyde α-sulfenylation followed by Corey−Fuchs alkynylation.

  通过炔丙基硫酰亚胺的[2,3]-σ重排，制备具有高水平对映体纯度的手性烯丙酰胺。所需的支链炔丙基硫化物是通过对映选择性有机催化醛α-亚磺酰基化，然后进行Corey-Fuchs炔基化反应制得的。