(+/-)-3-(triisopropylsilyloxy)-4-(2-(4-(triisopropylsilyloxy)phenethyl)-1,3-dithian-2-yl)butanal | 1240715-23-4

• 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: (+/-)-3-(triisopropylsilyloxy)-4-(2-(4-(triisopropylsilyloxy)phenethyl)-1,3-dithian-2-yl)butanal
• CAS: 1240715-23-4
• 化学式: C₃₄H₆₂O₃S₂Si₂
• 分子量: 639.167
• InChiKey: JOCUUKNEEKAVFV-UHFFFAOYSA-N

物化性质

• 沸点：
  619.2±55.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.28
• 重原子数：
  41.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+/-)-3-(triisopropylsilyloxy)-4-(2-(4-(triisopropylsilyloxy)phenethyl)-1,3-dithian-2-yl)butanal 、 1-三苯基膦-2-丙酮 以 甲苯 为溶剂， 以94%的产率得到(+/-)-(E)-6-(triisopropylsilyloxy)-7-(2-(4-(triisopropylsilyloxy)phenethyl)-1,3-dithian-2-yl)hept-3-en-2-one
  参考文献：
  名称：

  Hypervalent iodine(III)-mediated tandem oxidative reactions: application for the synthesis of bioactive polyspirocyclohexa-2,5-dienones

  摘要：

  In 2002, we reported the first total syntheses of potent antimalarial natural products, the aculeatins, employing the concept of tandem oxidative reactions mediated by hypervalent iodine(III) reagent to access to polyspirocyclohexa-2,5-dienone cores in very concise manner. Efforts in this field have allowed to identify cyclohexa-2,5-dienone group as a new potent class of pharmacophoric group for treating malaria disease. This article sums up recent contributions devoted to the synthesis of complex and diverse polycyclic structures using the concept of tandem oxidative activations, with p-phenol as co-reactant. More recently, we have explored a variant of the new tandem oxidative reactions that employs a catalytic amount of 4-iodotoluene in the presence of mCPBA as the stoichiometric oxidant (Kita's procedure). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.135
• 作为产物：
  描述：

  (+/-)-tert-butyl 3-(triisopropylsilyloxy)-4-(2-(4-(triisopropylsilyloxy)phenethyl)-1,3-dithian-2-yl)butanoate 在 二异丁基氢化铝 、 水 、 sodium hydroxide 作用下， 以 甲苯 、 甲醇 为溶剂， 以82%的产率得到(+/-)-3-(triisopropylsilyloxy)-4-(2-(4-(triisopropylsilyloxy)phenethyl)-1,3-dithian-2-yl)butanal
  参考文献：
  名称：

  Hypervalent iodine(III)-mediated tandem oxidative reactions: application for the synthesis of bioactive polyspirocyclohexa-2,5-dienones

  摘要：

  In 2002, we reported the first total syntheses of potent antimalarial natural products, the aculeatins, employing the concept of tandem oxidative reactions mediated by hypervalent iodine(III) reagent to access to polyspirocyclohexa-2,5-dienone cores in very concise manner. Efforts in this field have allowed to identify cyclohexa-2,5-dienone group as a new potent class of pharmacophoric group for treating malaria disease. This article sums up recent contributions devoted to the synthesis of complex and diverse polycyclic structures using the concept of tandem oxidative activations, with p-phenol as co-reactant. More recently, we have explored a variant of the new tandem oxidative reactions that employs a catalytic amount of 4-iodotoluene in the presence of mCPBA as the stoichiometric oxidant (Kita's procedure). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.135