5-(1,3-dithian-2-yl)pent-1-en-3-one | 1292793-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 5-(1,3-dithian-2-yl)pent-1-en-3-one
• CAS: 1292793-68-0
• 化学式: C₉H₁₄OS₂
• 分子量: 202.342
• InChiKey: QUKGCBNRVMGZJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(1,3-dithian-2-yl)pent-1-en-3-one 、 (S)-tert-butyl(hept-6-en-2-yloxy)dimethylsilane 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以76%的产率得到(9S,4E)-(9-tert-butyldimethylsilyloxy)-1-(1,3-dithian-2-yl)dec-4-en-3-one
  参考文献：
  名称：

  Formal total synthesis of aspergillide A

  摘要：

  The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C-4-C-14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into beta-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.016
• 作为产物：
  描述：

  3-(1,3-dithian-2-yl)-propanal 在 三氧化硫-三乙胺复合物 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.5h， 生成 5-(1,3-dithian-2-yl)pent-1-en-3-one
  参考文献：
  名称：

  Formal total synthesis of aspergillide A

  摘要：

  The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C-4-C-14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into beta-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.016

文献信息

• Formal total synthesis of aspergillide A
  作者：Yuko Izuchi、Nobuhiro Kanomata、Hiroyuki Koshino、Yayoi Hongo、Tadashi Nakata、Shunya Takahashi

  DOI：10.1016/j.tetasy.2011.01.016

  日期：2011.1

  The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C-4-C-14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into beta-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1. (C) 2011 Elsevier Ltd. All rights reserved.