3-<3-<(4-Methylbenzenesulfonyl)oxy>propyl>furan | 111931-57-8

• 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-<3-<(4-Methylbenzenesulfonyl)oxy>propyl>furan
• 英文别名: 3-(furan-3-yl)propyl p-toluenesulfonate；3-(furan-3-yl)propyl 4-methylbenzenesulfonate
• CAS: 111931-57-8
• 化学式: C₁₄H₁₆O₄S
• 分子量: 280.345
• InChiKey: NYVPAVGGJQHCJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  56.51
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-<3-<(4-Methylbenzenesulfonyl)oxy>propyl>furan 在 lithium bromide 作用下， 以 丙酮 、 苯 为溶剂， 反应 68.0h， 生成 <3-(3-Furyl)propyl>triphenylphosphonium Bromide
  参考文献：
  名称：

  Total synthesis of dehydroambliol-A and its unnatural Z isomer

  摘要：

  Convergent total syntheses of dehydroambliol-A (1a), its unnatural Z isomer 1b, and ambliofuran (2) are described. The syntheses utilized 2-(3'-furyl)-1,3-dithiane (6) as a common intermediate. Analysis of their proton and carbon magnetic resonance spectra confirm that in the natural product dehydroambliol-A and in synthetic dehydroambliol-A the DELTA-7-bond possesses the E geometry, while in the unnatural isomer of dehydroambliol-A, the DELTA-7-bond is of the Z configuration.

  DOI：

  10.1021/jo00009a033
• 作为产物：
  描述：

  3-<3-(Tetrahydropyran-2-yloxy)propyl>furan 在 吡啶 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 48.25h， 生成 3-<3-<(4-Methylbenzenesulfonyl)oxy>propyl>furan
  参考文献：
  名称：

  Total synthesis of dehydroambliol-A and its unnatural Z isomer

  摘要：

  Convergent total syntheses of dehydroambliol-A (1a), its unnatural Z isomer 1b, and ambliofuran (2) are described. The syntheses utilized 2-(3'-furyl)-1,3-dithiane (6) as a common intermediate. Analysis of their proton and carbon magnetic resonance spectra confirm that in the natural product dehydroambliol-A and in synthetic dehydroambliol-A the DELTA-7-bond possesses the E geometry, while in the unnatural isomer of dehydroambliol-A, the DELTA-7-bond is of the Z configuration.

  DOI：

  10.1021/jo00009a033

文献信息

• Anodic Cyclizations, Seven‐Membered Rings, and the Choice of Radical Cation vs. Radical Pathways
  作者：Robert J. Perkins、Ruozhu Feng、Qingquan Lu、Kevin D. Moeller

  DOI：10.1002/cjoc.201900132

  日期：2019.7

  the rest of the sequence is futile. We report here that the key to the cyclization is channeling the reaction down the correct pathway. Some reactions require the use of a radical pathway and some require the use of a radical cation pathway. An example of each is provided along with a strategy for accessing both pathways using a common intermediate.

  尽管氧化环化反应中的许多步骤可能很重要，但环化步骤本身才是中心作用。如果此步骤无法顺利进行，则其余序列的优化是徒劳的。我们在这里报告，环化的关键是引导反应沿着正确的途径进行。一些反应需要使用自由基途径，而某些则需要使用自由基阳离子途径。提供了每个示例的示例，以及使用公用中间体访问两个路径的策略。
• MAGATTI, CHARLES V.;KAMINSKI, JAMES J.;ROTHBERG, IRVIN, J. ORG. CHEM., 56,(1991) N, C. 3102-3108
  作者：MAGATTI, CHARLES V.、KAMINSKI, JAMES J.、ROTHBERG, IRVIN

  DOI：——

  日期：——
• Concise synthesis and structure–activity relationship of furospinosulin-1, a hypoxia-selective growth inhibitor from marine sponge
  作者：Naoyuki Kotoku、Shinichi Fujioka、Chiaki Nakata、Masaki Yamada、Yuji Sumii、Takashi Kawachi、Masayoshi Arai、Motomasa Kobayashi

  DOI：10.1016/j.tet.2011.05.009

  日期：2011.9

  Structure activity relationship of furospinosulin-1 (1), a hypoxia-selective growth inhibitor isolated from marine sponge, was investigated. Concise synthetic method of 1 was developed, and some structurally modified analogues were prepared. Biological evaluation of them revealed that the whole chemical structure was important for the hypoxia-selective growth inhibitory activity of 1. Among prepared, the desmethyl analogue 30 showed excellent hypoxia-selective inhibitory activity similar to that of 1 and also exhibited in vivo anti-tumor activity with oral administration. (C) 2011 Elsevier Ltd. All rights reserved.
• Total synthesis of dehydroambliol-A and its unnatural Z isomer
  作者：Charles V. Magatti、James J. Kaminski、Irvin Rothberg

  DOI：10.1021/jo00009a033

  日期：1991.4

  Convergent total syntheses of dehydroambliol-A (1a), its unnatural Z isomer 1b, and ambliofuran (2) are described. The syntheses utilized 2-(3'-furyl)-1,3-dithiane (6) as a common intermediate. Analysis of their proton and carbon magnetic resonance spectra confirm that in the natural product dehydroambliol-A and in synthetic dehydroambliol-A the DELTA-7-bond possesses the E geometry, while in the unnatural isomer of dehydroambliol-A, the DELTA-7-bond is of the Z configuration.