(3-bromofuran-2-yl)trimethylsilane | 38611-21-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3-bromofuran-2-yl)trimethylsilane
• 英文别名: 2-trimethylsilyl-3-bromofuran；(3-bromofuran-2-yl)-trimethylsilane
• CAS: 38611-21-1
• 化学式: C₇H₁₁BrOSi
• 分子量: 219.153
• InChiKey: VDRYRSSOANYBEA-UHFFFAOYSA-N

物化性质

• 沸点：
  183.3±25.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  10
• 可旋转键数：
  1
• 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-奎宁环酮 、 (3-bromofuran-2-yl)trimethylsilane 在 lithium diisopropyl amide 作用下， 生成 3-(4-Bromo-5-trimethylsilanyl-furan-2-yl)-1-aza-bicyclo[2.2.2]octan-3-ol
  参考文献：
  名称：

  Antimuscarinic 3-(2-Furanyl)quinuclidin-2-ene Derivatives:  Synthesis and Structure−Activity Relationships

  摘要：

  A series of 25 derivatives of the muscarinic antagonist 3-(2-furanyl)quinuclidin-2-ene (4) was synthesized and evaluated for muscarinic and antimuscarinic properties. Substitution at all three positions of the furan ring has been investigated. The affinities of the new compounds were determined by competition experiments in homogenates of cerebral cortex, heart, parotid gland, and urinary bladder from guinea pigs using (-)-[H-3]-3-quinuclidinyl benzilate as the radioligand, and the antimuscarinic potency was determined in a functional assay on isolated guinea pig urinary bladder using carbachol as the agonist. Several of the novel derivatives displayed high muscarinic affinities. Whereas the affinity of lead compound 4 for cortical muscarinic receptors is moderate (K-i 300 nM), it is much higher for the 6-methyl (49; K-i = 12 nM), 5-ethyl (52; K-i = 7.4 nM), 5-bromo (33; K-i = 6.4 nM), and 3-phenyl (49; K-i = 2.8 nM) substituted derivatives. The substituent-induced increases in affinity do not appear to be additive as a 5-bromo-3-phenyl (54), and a 5-methyl-3-phenyl (55) substitution pattern only slightly increases affinity (K-i = 1.55 and 2.39 nM, respectively). The conformational preferences of the 3-phenyl (49) and 5-phenyl (51) derivatives were studied by X-ray crystallography and molecular mechanics calculations. Because of the observed high affinity of 49, a series of 16 meta-and para-substituted analogues of 49 was synthesized and tested. derivative (68) exhibited more than 10-fold improvement in affinity as compared to 49. The structure-activity relationships of the new series are well described with QSAR and CoMFA models.

  DOI：

  10.1021/jm970346t
• 作为产物：
  描述：

  2,4-二溴-5-(三甲基甲硅烷基)呋喃 在 正丁基锂 、 水 作用下， 生成 (3-bromofuran-2-yl)trimethylsilane
  参考文献：
  名称：

  Two syntheses of manoalide via heteroatom-assisted alkyne carbometallation

  摘要：

  Two approaches to the sesterterpenoid phospholipase A(2) inhibitors seco-manoalide (3) and manoalide (1) are described based on carbometallation of propargylic alcohols to generate the functionalised C6-C7 trisubstituted alkene. Both syntheses also deploy the photooxidation of a furan in order to generate a 4-substituted-5-hydroxy-2(5H)-furanone moiety.

  DOI：

  10.1016/s0040-4020(01)85353-9

文献信息

• Urokinase inhibitors
  申请人：Abbott Laboratories

  公开号：US06258822B1

  公开（公告）日：2001-07-10

  Compounds having the formula are inhibitors of urokinase and are useful in the treatment of diseases in which urokinase plays a role. Also disclosed are urokinase-inhibiting compositions and a method of inhibiting urokinase in a mammal.

  具有该公式的化合物是尿激酶的抑制剂，对于尿激酶在其中发挥作用的疾病的治疗是有用的。还公开了抑制尿激酶的组合物和在哺乳动物中抑制尿激酶的方法。
• Ukokinase inhibitors
  申请人：Abbott Laboratories

  公开号：US06284796B1

  公开（公告）日：2001-09-04

  Compounds having the formula are inhibitors of urokinase and are useful in the treatment of diseases in which urokinase plays a role. Also disclosed are urokinase-inhibiting compositions and a method of inhibiting urokinase in a mammal.

  具有该化学式的化合物是尿激酶的抑制剂，对于尿激酶在某些疾病治疗中起作用是有用的。还公开了抑制尿激酶的组合物和在哺乳动物中抑制尿激酶的方法。
• Interaction with the S1β-pocket of urokinase: 8-heterocycle substituted and 6,8-disubstituted 2-naphthamidine urokinase inhibitors
  作者：Michael D. Wendt、Andrew Geyer、William J. McClellan、Todd W. Rockway、Moshe Weitzberg、Xumiao Zhao、Robert Mantei、Kent Stewart、Vicki Nienaber、Vered Klinghofer、Vincent L. Giranda

  DOI：10.1016/j.bmcl.2004.04.030

  日期：2004.6

  Several 8-substituted 2-naphthamidine-based inhibitors of the serine protease urokinase plasminogen activator (uPA) are described. Direct attachment of five-membered saturated or unsaturated rings improved inhibitor performance; substitution with sulfones further improved binding profiles. Combination of these substituents or of previously described NH-linked heteroaromatic rings with 6-phenyl amide substituents provided further enhancements to potency and selectivity. (C) 2004 Elsevier Ltd. All rights reserved.
• Directed metalation and regioselective functionalization of 3-bromofuran and related heterocycles with NaHMDS
  作者：Hang Zhao、John W. Dankwardt、Stefan G. Koenig、Surendra P. Singh

  DOI：10.1016/j.tetlet.2011.10.158

  日期：2012.1

  A mild and regioselective functionalization protocol for 3-bromofuran and analogs has been developed. Selective metalation and functionalization of C2 can be achieved as a result of the directing effect of the adjacent electron-withdrawing bromo group. In addition, the C5 position can also be selectively functionalized by blocking the C2 position via silylation or by simply controlling the reaction temperature. These functionalized compounds bearing a C3 bromo substituent may be further elaborated by utilizing a Suzuki-Miyaura cross-coupling procedure. (C) 2011 Elsevier Ltd. All rights reserved.
• General Strategies for the Synthesis of the Major Classes of <i>C</i>-Aryl Glycosides
  作者：David E. Kaelin、Omar D. Lopez、Stephen F. Martin

  DOI：10.1021/ja0108640

  日期：2001.7.1