4,4-bis(3-methyl-2-thienyl)but-3-en-1-ol | 847233-27-6

• 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: 4,4-bis(3-methyl-2-thienyl)but-3-en-1-ol
• 英文别名: 4,4-bis(3-methyl-2-thienyl)-3-buten-1-ol；4,4-bis(3-methylthiophen-2-yl)but-3-en-1-ol
• CAS: 847233-27-6
• 化学式: C₁₄H₁₆OS₂
• 分子量: 264.412
• InChiKey: ATLROBDAMPSMRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4-bis(3-methyl-2-thienyl)but-3-en-1-ol 在 C₆₃H₇₈IrNOP⁽²⁺⁾*C₃₂H₁₂BF₂₄^(1-) 、 氢气 、 potassium carbonate 、 三乙胺 、 potassium iodide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醚 、 水 、 丙酮 为溶剂， 20.0~60.0 ℃ 、607.99 kPa 条件下， 反应 135.0h， 生成 噻加宾
  参考文献：
  名称：

  铱催化不饱和杂环酸的对映选择性加氢

  摘要：

  螺旋结合：一种高度对映选择性的不饱和杂环羧酸的加氢已经通过使用手性铱/ spirophosphino恶唑啉催化剂开发（参见方案; BAR ˚F - =四[3,5-双（三氟甲基）苯基]硼酸盐，的Boc =叔丁氧羰基） 。该反应提供了制备具有优异对映选择性的旋光杂环酸的有效方法。

  DOI：

  10.1002/anie.201301341
• 作为产物：
  描述：

  1,1-双(3-甲基噻吩-2-基)丁烷-1,4-二醇 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 4,4-bis(3-methyl-2-thienyl)but-3-en-1-ol
  参考文献：
  名称：

  铱催化不饱和杂环酸的对映选择性加氢

  摘要：

  螺旋结合：一种高度对映选择性的不饱和杂环羧酸的加氢已经通过使用手性铱/ spirophosphino恶唑啉催化剂开发（参见方案; BAR ˚F - =四[3,5-双（三氟甲基）苯基]硼酸盐，的Boc =叔丁氧羰基） 。该反应提供了制备具有优异对映选择性的旋光杂环酸的有效方法。

  DOI：

  10.1002/anie.201301341

文献信息

• Ring-chain tautomerism in 2,2-bis(2-thienyl)tetrahydrofurans: preparation of [butene-2H5]-tiagabine
  作者：John M. Herbert、Trevor W. Mathers

  DOI：10.1002/jlcr.1787

  日期：2010.7

  A concise preparation of [butene-2H5]-tiagabine hydrochloride starting from [2H6]-γ-butyrolactone is described. It was necessary to ring-open the labeled γ-butyrolactone precursor before the addition of 2-thienyllithium to avoid cyclisation of the intermediate to a 2,2-bis(2-thienyl)tetrahydrofuran. Copyright © 2010 John Wiley & Sons, Ltd.

  描述了从 [2H6]-γ-丁内酯开始的 [丁烯-2H5]-tiagabine 盐酸盐的简明制备。有必要在添加 2-噻吩基锂之前将标记的 γ-丁内酯前体开环，以避免中间体环化为 2,2-双（2-噻吩基）四氢呋喃。版权所有 © 2010 John Wiley & Sons, Ltd.
• A Highly Efficient Conversion of Primary or Secondary Alcohols into Fluorides with <i>n</i>-Perfluorobutanesulfonyl Fluoride-Tetrabutylammonium Triphenyldifluorosilicate
  作者：Xueqing Zhao、Xiaowen Xue、Weiping Zhuang、Dongsheng Fang、Jingming Zhou

  DOI：10.1055/s-0028-1087931

  日期：——

  Direct fluorination of primary and secondary alcohols by a combination of perfluoro-1-butanesulfonyl fluoride (PBSF) and tetrabutylammonium triphenyldifluorosilicate (TBAT) under mild conditions provides the corresponding fluorides in high yields. With this combination, elimination side reactions could be significantly suppressed and chiral secondary alcohols were less prone to epimerization at the reaction center.

  在温和的条件下，全氟-1-丁磺酰氟（PBSF）和四丁基三苯基氟硅酸铵（TBAT）组合对伯醇和仲醇进行直接氟化反应，可获得高产率的相应氟化物。在这种组合下，消除副反应的效果明显减弱，手性仲醇在反应中心也不易发生缩合反应。
• Selective inhibitors of GABA uptake: synthesis and molecular pharmacology of 4-N-methylamino-4,5,6,7-tetrahydrobenzo[d]isoxazol-3-ol analogues
  作者：Rasmus P. Clausen、Ejner K. Moltzen、Jens Perregaard、Sibylle M. Lenz、Connie Sanchez、Erik Falch、Bente Frølund、Tina Bolvig、Alan Sarup、Orla M. Larsson、Arne Schousboe、Povl Krogsgaard-Larsen

  DOI：10.1016/j.bmc.2004.10.029

  日期：2005.2

  A series of lipophilic diaromatic derivatives of the glia-selective GABA uptake inhibitor (R)-4-amino-4,5,6,7-tetrahydrobenzo[d]isoxazol-3-ol [(R)-exo-THPO, 4] were synthesized via reductive amination of 3-ethoxy-4,5,6,7-tetrahydrobenzo[d]isoxazol-4-one (9) or via N-alkylation of O-alkylatedracemic 4. The effects of the target compounds on GABA uptake mechanisms in vitro were measured using a rat brain synaptosomal preparation or primary cultures of mouse cortical neurons and glia cells (astrocytes), as well as HEK cells transfected with cloned mouse GABA transporter subtypes (GAT1-4). The activity against isoniazid-induced convulsions in mice after subcutaneous administration of the compounds was determined. All of the compounds were potent inhibitors of synaptosomal uptake the most potent compound being (RS)-4-[N-(1,1-diphenylbut-1-4-en-yl)amino]-4,5,6,7-tetrahydrobenzo[d]isoxazol-3-ol (17a, IC50 = 0.14 muM). The majority of the compounds showed a weak preference for glial, as compared to neuronal, GABA uptake. The highest degree of selectivity was 10-fold corresponding to the glia selectivity of (R)-N-methyl-exo-THPO (5). All derivatives showed a preference for the GAT1 transporter, as compared with GAT2-4, with the exception of (RS)-4-[N-[1,1-bis(3-methyl-2-thienyl)but-1-en-4-yl]-N-methylamino]-4,5,6,7-tetrahydrobenzo[d]isoxazol-3-ol (28d), which quite surprisingly turned out to be more potent than GABA at both GAT1 and GAT2 subtypes. The GAT1 activity was shown to reside in (R)-28d whereas (R)-28d and (S)-28d contributed equally to GAT2 activity. This makes (S)-28d a GAT2 selective compound, and (R)-28d equally effective in inhibition of GAT1 and GAT2 mediated GABA transport. All compounds tested were effective as anticonvulsant reflecting that these compounds have blood-brain barrier permeating ability. (C) 2004 Elsevier Ltd. All rights reserved.
• Iridium-Catalyzed Enantioselective Hydrogenation of Unsaturated Heterocyclic Acids
  作者：Song Song、Shou-Fei Zhu、Liu-Yang Pu、Qi-Lin Zhou

  DOI：10.1002/anie.201301341

  日期：2013.6.3

  binding: A highly enantioselective hydrogenation of unsaturated heterocyclic acids has been developed by using chiral iridium/spirophosphino oxazoline catalysts (see scheme; BArF−=tetrakis[3,5‐bis(trifluoromethyl)phenyl]borate, Boc=tert‐butoxycarbonyl). This reaction provided an efficient method for the preparation of optically active heterocyclic acids with excellent enantioselectivities.

  螺旋结合：一种高度对映选择性的不饱和杂环羧酸的加氢已经通过使用手性铱/ spirophosphino恶唑啉催化剂开发（参见方案; BAR ˚F - =四[3,5-双（三氟甲基）苯基]硼酸盐，的Boc =叔丁氧羰基） 。该反应提供了制备具有优异对映选择性的旋光杂环酸的有效方法。