<3-(3-Furyl)propyl>triphenylphosphonium Bromide | 132912-33-5

• 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-Furyl)propyl>triphenylphosphonium Bromide
• 英文别名: [3-(furan-3-yl)propyl]triphenylphosphonium bromide；[3-(3'-furyl)propyl]triphenylphosphonium bromide；3-(Furan-3-yl)propyl-triphenylphosphanium;bromide
• CAS: 132912-33-5
• 化学式: Br*C₂₅H₂₄OP
• 分子量: 451.343
• InChiKey: YYURIUNNRDMGEW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <3-(3-Furyl)propyl>triphenylphosphonium Bromide 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl-[(3S)-4-[2-[(E)-5-(furan-3-yl)-2-methylpent-2-enyl]-1,3-dithian-2-yl]-3-methylbutoxy]-dimethylsilane
  参考文献：
  名称：

  Synthesis of (-)-Untenospongin C, a C21 Furanoterpene Isolated from the Okinawan Sponge Hippospongia Sp.

  摘要：

  Starting with (R)-(+)-citronellol (5), the first enantioselective synthesis of (-)-untenospongin C (1), a C-21 furanoterpene isolated from a marine sponge Hippospongia sp., has been achieved, the present synthesis indicating the absolute configuration of 1 as S.

  DOI：

  10.3987/com-11-12302
• 作为产物：
  描述：

  2-(3'-Furyl)-2-<2-(tetrahydropyran-2-yloxy)ethyl>-1,3-dithiane 在 氨 、 溴 、 sodium 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 48.75h， 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

文献信息

• Studies on furoterpenes: Stereoselective total synthesis of (±)-Ambliol-A and Dendrolasin
  作者：Arindam Chakraborty、Gandhi K Kar、Jayanta K Ray

  DOI：10.1016/s0040-4020(97)00509-7

  日期：1997.6

  (±)-Ambliol-A (1) is totally synthesised with high stereoselectivity starting from α-ionone and [3-(3′-furyl)propyl]triphenylphosphonium bromide (3). In another attempt utilising 3 with the commercially available ketone 11 the total synthesis of Dendrolasin (12) has also been achieved.

  （±）-Ambliol-A（1）以α-紫罗兰酮和[3-（3'-呋喃基）丙基]三苯基溴化（（3）为原料，以高立体选择性完全合成。在利用3与可商购的酮11一起进行的另一尝试中，也已经实现了Dendrolasin（12）的全合成。
• Isolation, Structure Elucidation, and Total Synthesis of Dolichovespulide, a Sesquiterpene from <i>Dolichovespula</i> Yellowjackets
  作者：Weiwu Ren、Regine Gries、Kenji L. Kurita、Catherine S. McCaughey、Santosh K. Alamsetti、Roger G. Linington、Gerhard Gries、Robert Britton

  DOI：10.1021/acs.jnatprod.9b00238

  日期：2019.7.26

  sexual communication in yellowjacket wasps, a novel sesquiterpene was isolated from body surface extracts of virgin bald-faced hornet queens, Dolichovespula maculata. The gross structure of this sesquiterpene was proposed through microscale spectroscopic analyses, and the configuration of the central olefin was subsequently confirmed by total synthesis. This new natural product (termed here dolichovespulide)

  作为一项正在进行的程序的一部分，该程序可识别介导黄夹克黄蜂中性交的性吸引信息素成分，从纯净秃顶的大黄蜂女王Dolichovespula maculata的体表提取物中分离出一种新型倍半萜。该倍半萜烯的总体结构是通过微观光谱分析提出的，随后通过全合成证实了中心烯烃的构型。这种新的天然产物（在这里称为多柔胆素）代表了从分类昆虫类维斯匹虫科中报告的相对少量的萜类化合物的重要添加。
• 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 of (-)-Untenospongin C, a C21 Furanoterpene Isolated from the Okinawan Sponge Hippospongia Sp.
  作者：Yoshihiro Noda、Shuji Ugajin、Akihiko Yamanaka、Natsuki Mamiya

  DOI：10.3987/com-11-12302

  日期：——

  Starting with (R)-(+)-citronellol (5), the first enantioselective synthesis of (-)-untenospongin C (1), a C-21 furanoterpene isolated from a marine sponge Hippospongia sp., has been achieved, the present synthesis indicating the absolute configuration of 1 as S.
• 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.