3-(3'-iodopropyl)furan | 195703-11-8

• 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: 3-(3'-iodopropyl)furan
• 英文别名: 3-(3-Iodopropyl)furan
• CAS: 195703-11-8
• 化学式: C₇H₉IO
• 分子量: 236.052
• InChiKey: HZWVGONLCSCGTE-UHFFFAOYSA-N

物化性质

• 沸点：
  213.5±23.0 °C(Predicted)
• 密度：
  1.681±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  3-(3'-iodopropyl)furan 在 sodium cyanide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以99%的产率得到4-(3-furyl)-1-butanenitrile
  参考文献：
  名称：

  The first enantioselective synthesis of palinurin

  摘要：

  从市售的呋喃甲醛和 (R)-3- 羟基-2-甲基丙酸甲酯开始，首次完成了对映体选择性合成 Palinurin；合成的关键步骤包括使用手性吡咯烷生成手性四分子，以及通过 Horner-Wadsworth-Emmons、Wittig 和 Wittig-Horner 反应构建烯单元。

  DOI：

  10.1039/b822679b
• 作为产物：
  描述：

  3-(3'-hydroxypropyl)furan mesylate 在 lithium iodide 作用下， 以 丙酮 为溶剂， 反应 7.0h， 以83%的产率得到3-(3'-iodopropyl)furan
  参考文献：
  名称：

  Oxidative Cyclizations:  The Asymmetric Synthesis of (−)-Alliacol A

  摘要：

  A tandem anodic coupling-Friedel-Crafts alkylation strategy has been used to rapidly complete the asymmetric synthesis of alliacol A. The anodic oxidation reaction allowed for the generation of a new bond between two nucleophiles. In the synthesis, the absolute stereochemistry of the final natural product is set relative to a methyl group that is incorporated early in the sequence using an asymmetric Michael reaction.

  DOI：

  10.1021/ja048085h

文献信息

• Furan derivatives, method of synthesis and uses thereof
  申请人：Neuropharma S.A.

  公开号：EP1939191A1

  公开（公告）日：2008-07-02

  The present invention relates to furan derivatives of formula (I), their method of synthesis and uses thereof. Concretely, the compounds disclosed have proved to be inhibitors of glycogen synthase kinase 3β, GSK-3 β, which is known to be involved in different disease and conditions, such as Alzheimer's disease or non-insulin dependent diabetes mellitus. The present invention also relates to pharmaceutical compositions comprising the same. Further, the present invention is directed to the use of the compounds in the manufacture of a medicament for the treatment and/or prevention of a GSK-3 mediated disease or condition.

  本发明涉及式(I)的呋喃衍生物，其合成方法及用途。具体来说，所披露的化合物已被证明是糖原合成酶激酶3β（GSK-3β）的抑制剂，GSK-3β已知参与不同疾病和病况，如阿尔茨海默病或非胰岛素依赖型糖尿病。本发明还涉及包含这些化合物的药物组合物。此外，本发明旨在将这些化合物用于制造治疗和/或预防GSK-3介导的疾病或病况的药物。
• Ruthenium-Catalyzed Asymmetric Dehydrative Allylic Cyclization of Five-Membered Chalcogen Heteroaromatics
  作者：Shinji Tanaka、Masato Kitamura、Shoutaro Iwase、Sena Kanda、Marie Kato、Yutaro Kiriyama

  DOI：10.1055/a-1523-6826

  日期：2021.9

  intramolecular allylation reactions of furan and thiophene were performed using a cationic cyclopentadienyl-ruthenium (CpRu) complex of a chiral pyridine carboxylic acid, namely Cl-Naph-PyCOOH. Both furan and thiophene tethered with an allylic alcohol gave the corresponding bicyclic compounds in high yields and enantioselectivities using 0.1–5 mol% of the catalyst. The reaction was found to proceed via

  呋喃和噻吩的不对称脱水分子内烯丙基化反应使用手性吡啶羧酸（即 Cl-Naph-PyCOOH）的阳离子环戊二烯基-钌 (CpRu) 络合物进行。呋喃和噻吩与烯丙醇相连，使用 0.1-5 mol% 的催化剂以高产率和对映选择性得到相应的双环化合物。发现该反应通过与我们小组先前报道的类似的对映面选择机制进行，除了生成中间体 σ-烯丙基复合物外，还涉及卤素和氢键的形成。
• Total syntheses of the furanosesquiterpenes crassifolone and dihydrocrassifolone via an Au(i)-catalysed intramolecular Michael addition reaction
  作者：Rajeev S. Menon、Martin G. Banwell

  DOI：10.1039/c0ob00487a

  日期：——

  The racemic modifications of title natural products 1 and 2 have been synthesised for the first time. The key step was the Au(I)-catalysed conversion of the furanyl-substituted ynone 13 into the annulated furan 14.

  标题天然产物1和2的外消旋体修饰是首次合成。关键步骤是Au（I）催化的呋喃基取代的炔酮13转化为环状呋喃14。
• Type II Intramolecular [5+2] Cycloaddition: Facile Synthesis of Highly Functionalized Bridged Ring Systems
  作者：Guangjian Mei、Xin Liu、Chuang Qiao、Wei Chen、Chuang-chuang Li

  DOI：10.1002/anie.201410806

  日期：2015.2.2

  formation of various highly functionalized and synthetically challenging bridged seven‐membered ring systems (such as bicyclo[4.4.1]undecane, bicyclo[4.3.1]decane, bicyclo[5.4.1]dodecane, and bicyclo[6.4.1]]tridecane). This simple, thermal, direct transformation has a broad substrate scope and is high yielding, with high functional‐group tolerance and unique endo selectivity. The highly strained tricyclic

  II型分子内氧化吡啶介导的[5 + 2]环加成反应可有效且非对映选择性地形成各种高度官能化且具有合成挑战性的桥连七元环系统（例如双环[4.4.1]十一烷，双环[4.3.1]）癸烷，双环[5.4.1]十二烷和双环[6.4.1]]十三烷）。这种简单，热，直接的转化具有广泛的底物范围，产量高，具有较高的官能团耐受性和独特的内在选择性。使用这种方法可高效合成非对映异构体，其中包括丁二酸丁二醇酯（吡啶）和环柠檬醇的高应变三环核。
• Synthesis and phosphatase inhibitory activity of analogs of sulfircin
  作者：Regina E. Cebula、Jill L. Blanchard、Michael D. Boisclair、Kollol Pal、Nicholas J. Bockovich

  DOI：10.1016/s0960-894x(97)00357-0

  日期：1997.8

  Analogs of sulfircin (1) were synthesized and tested for inhibitory activity against a panel of phosphatases. We attempted to optimize the potency and selectivity of sulfircin for Cdc25A by modifying three structural areas of the molecule. An anionic group is required for potency and malonate was found to be an effective substitute for sulfate. (C) 1997 Elsevier Science Ltd.