(E)-3-(5-bromo-4-methylpent-3-enyl)furan | 131497-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E)-3-(5-bromo-4-methylpent-3-enyl)furan
• 英文别名: 3-[(E)-5-bromo-4-methylpent-3-enyl]furan
• CAS: 131497-07-9
• 化学式: C₁₀H₁₃BrO
• 分子量: 229.117
• InChiKey: NEJONXIIMGKYHR-YCRREMRBSA-N

物化性质

• 沸点：
  269.2±28.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3-(5-bromo-4-methylpent-3-enyl)furan 在 silver trifluoroacetate 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 Dehydrolasiosperman
  参考文献：
  名称：

  A short route to furanosesquiterpenes using a new siloxyfuran building block. The synthesis of freelingnite and dehydrolasiosperman

  摘要：

  DOI：

  10.1016/s0040-4039(00)97946-2
• 作为产物：
  描述：

  3-呋喃甲醇 在 吡啶 、 lithium aluminium tetrahydride 、 四溴化碳 、 三溴化磷 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (E)-3-(5-bromo-4-methylpent-3-enyl)furan
  参考文献：
  名称：

  A short route to furanosesquiterpenes using a new siloxyfuran building block. The synthesis of freelingnite and dehydrolasiosperman

  摘要：

  DOI：

  10.1016/s0040-4039(00)97946-2

文献信息

• 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.
• Synthesis and evaluation of effective photoaffinity probe molecule of furospinosulin-1, a hypoxia-selective growth inhibitor
  作者：Naoyuki Kotoku、Chiaki Nakata、Takashi Kawachi、Takanori Sato、Xiu-Han Guo、Aoi Ito、Yuji Sumii、Masayoshi Arai、Motomasa Kobayashi

  DOI：10.1016/j.bmc.2014.02.026

  日期：2014.4

  The synthesis and evaluation of a photoaffinity probe molecule for furospinosulin-1, a hypoxia-selective growth inhibitor that we identified from marine sponge, was studied. An analogue carrying an alkyne tail showed potent hypoxia-selective inhibitory activity exceeding that of the parent molecule, and exhibited in vivo anti-tumor activity following oral administration. The alkyne moiety in the analogue was also found to be a good anchoring group for the preparation of probe molecules; a photoaffinity probe molecule having an optimized spacer length was selected through the systematic synthesis of several probes and the evaluation of their hypoxia-selective growth inhibitory activity and electrophoretic mobility shift properties. (C) 2014 Elsevier Ltd. All rights reserved.
• SHAPIRO, GIDEON;BUECHLER, DIETER;HENNET, SYLVIE, TETRAHEDRON LETT., 31,(1990) N0, C. 5733-5736
  作者：SHAPIRO, GIDEON、BUECHLER, DIETER、HENNET, SYLVIE

  DOI：——

  日期：——
• US9371301B2
  申请人：——

  公开号：US9371301B2

  公开（公告）日：2016-06-21