(E)-5-(呋喃-3-基)-2-甲基戊-2-烯酸乙酯 | 180334-02-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (E)-5-(呋喃-3-基)-2-甲基戊-2-烯酸乙酯
• 英文名称: (E)-5-(furan-3-yl)-2-methylpent-2-enoic acid ethyl ester
• 英文别名: ethyl (E)-5-(3'-furyl)-2-methyl-2-pentenoate；ethyl (E)-5-(furan-3-yl)-2-methylpent-2-enoate
• CAS: 180334-02-5
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: UPNBHMQZKXFDOM-BJMVGYQFSA-N

物化性质

• 沸点：
  289.4±28.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-(呋喃-3-基)-2-甲基戊-2-烯酸乙酯 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(E)-5-(呋喃-3-基)-2-甲基戊-2-烯-1-醇
  参考文献：
  名称：

  A highly convergent enantioselective total synthesis of marine natural product, furanoterpene

  摘要：

  实现了海洋呋喃萜烯 1 的对映选择性全收敛合成，并发现唯一存在的四元立体中心的绝对构型为 S。

  DOI：

  10.1039/cc9960001357
• 作为产物：
  描述：

  trans-3-呋喃丙烯酸 在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 0.5h， 生成 (E)-5-(呋喃-3-基)-2-甲基戊-2-烯酸乙酯
  参考文献：
  名称：

  Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization – electrophilic aromatic substitution

  摘要：

  1,4-二烯-3-酮，其C-1位上连接有悬垂的芳基乙基侧链，可从取代的二氢肉桂醛中方便地制备。在低温下使用TiCl4处理，可在5分钟内实现多米诺Nazarov电环化-芳环捕捉反应，以近定量的产率和完全的非对映选择性得到外消旋苯并吲哚酮。关键词：多米诺过程，亲电芳香取代，路易斯酸，Nazarov环化。

  DOI：

  10.1139/v03-203

文献信息

• Highly Efficient Trapping of the Nazarov Intermediate with Substituted Arenes
  作者：Cindy C. Browder、Fredrik P. Marmsäter、F. G. West

  DOI：10.1021/ol010159w

  日期：2001.9.1

  [GRAPHICS]1,4-Dien-3-ones bearing pendant arylethyl side chains were readily prepared from substituted dihydrocinnamaldehydes. When treated with TiCl4 at low temperature, these compounds underwent domino cyclization to give benzohydrindenones in near-quantitative yield and with complete diastereoselectivity.
• 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.
• NOVEL PRENYLARENE COMPOUND AND USE THEREOF
  申请人：Kobayashi Motomasa

  公开号：US20130065937A1

  公开（公告）日：2013-03-14

  A compound represented by the general formula (C): (wherein R 101 represents a substituted or unsubstituted aromatic heterocyclic group, R 102 , R 103 , R 104 and R 105 may be the same or different, and each represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms, or a haloalkyl group having 1 to 3 carbon atoms, and R 106 represents a hydrogen atom, or a saturated or unsaturated hydrocarbon group which is a straight or branched chain having 1 to 12 carbon atoms, but excluded is the case where R 101 is a 3-furyl group, R 102 , R 103 , R 104 and R 105 are all methyl groups, and R 106 is a methyl group, a 4-methyl-3-pentenyl group or a 4,8-dimethyl-3,7-nonadienyl group); or a pharmaceutically acceptable salt thereof has selective inhibitory activity on hypoxic cell growth in a broad range of the concentration and therefore is useful as an active ingredient of a medicament for cancer prevention or treatment.
• US9371301B2
  申请人：——

  公开号：US9371301B2

  公开（公告）日：2016-06-21