(E)-methyl 3-(benzo[b]thiophen-2-yl)acrylate | 65942-75-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (E)-methyl 3-(benzo[b]thiophen-2-yl)acrylate
• 英文别名: methyl (E)-3-(benzo[b]thiophen-2-yl)acrylate；3t-benzo[b]thiophen-2-yl-acrylic acid methyl ester；3t-Benzo[b]thiophen-2-yl-acrylsaeure-methylester；methyl (E)-3-(1-benzothiophen-2-yl)prop-2-enoate
• CAS: 65942-75-8
• 化学式: C₁₂H₁₀O₂S
• 分子量: 218.276
• InChiKey: XZWVJNJOWOJHFI-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-methyl 3-(benzo[b]thiophen-2-yl)acrylate 在 palladium diacetate 、 sodium hydroxide 、 sodium azide 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 11.0h， 生成
  参考文献：
  名称：

  trans-2-Aryl-N,N-dipropylcyclopropylamines:  Synthesis and Interactions with 5-HT_1A Receptors

  摘要：

  Twelve N,N-dipropyl-substituted derivatives of trans-2-arylcyclopropylamine have been prepared and assayed for their ability to displace [H-3]-8-OH-DPAT from rat brain 5-HT1A receptors. The new derivatives include phenyl (7a), bromo- (7b) and fluorophenyl (7c-e), 2-methoxy-5-fluorophenyl (7h), and 2-hydroxy-5-fluorophenyl (7I) as well as trifluoromethylphenyl (7f) and 2,3-dichlorophenyl (7g) analogues. In the present series of compounds, electron-withdrawing substituents in the phenyl ring appear to decrease the affinity for 5-HT1A receptors. In contrast, electron-rich aryl groups, such as 2- or 3-thienyl (7j and 7k, respectively), provide compounds with high affinity. The additional bulk produced by the aromatic moiety in the 2-benzothienyl derivative 7i appears to be detrimental to 5-HT1A receptor affinity. The racemic mixtures of the interesting 7j and 7I were resolved into the enantiomers; 7j and 7I exhibited a high enantiomeric 5-HT1A receptor affinity ratio (75-fold and 100-fold, respectively). The enantiomers of 7j and 7I were evaluated in vivo by use of biochemical and behavioral tests in rats. Compound (LR,2R)-7j behaved as a partial agonist whereas (1R,2S)-7I appeared as an efficacious 5-HT1A receptor agonist, stimulating both autoreceptors and postsynaptic receptors.

  DOI：

  10.1021/jm9507136
• 作为产物：
  描述：

  1-苯并噻酚-2-羧醛 在 哌啶 、 1,4-二氧六环 、 吡啶 、 乙醚 作用下， 生成 (E)-methyl 3-(benzo[b]thiophen-2-yl)acrylate
  参考文献：
  名称：

  Heterocyclic Analogs of the Estrogenic Steroid Hormones. I. Synthesis of a Thiophene Analog of 3-Desoxyisoequilenin^1,2

  摘要：

  DOI：

  10.1021/ja01562a024

文献信息

• Phosphetane Oxides as Redox Cycling Catalysts in the Catalytic Wittig Reaction at Room Temperature
  作者：Lars Longwitz、Anke Spannenberg、Thomas Werner

  DOI：10.1021/acscatal.9b02456

  日期：2019.10.4

  renewable solvent. The intermediates of the Wittig reaction were analyzed by 31P NMR spectroscopy, and in situ NMR experiments confirmed phosphane oxide as the resting state of the catalyst. Further kinetic investigations revealed a striking influence of the base on the rate of phosphane oxide reduction.

  近来，磷氧化还原循环对于最初要求使用化学计量的磷试剂的许多转化已变得非常重要。尽管这些方法具有多种优势，但催化剂负载量高（≥10 mol％）和苛刻的反应条件（T≥100°C）通常会限制其通用性和适用性。在本文中，我们报道了不同取代的氧化膦作为有效的Wittig反应催化剂。磷脂骨架易于修饰，并且可以通过简单的两步合成获得多种催化剂。Wittig反应中的活性大大超过了先前报道的基于磷杂环戊烷的催化剂，并且即使在室温下，该反应也可以以低至1.0 mol％的催化剂负载量进行。此外，在这些温和条件下不再需要布朗斯台德酸添加剂即可实现高收率。甲基取代的氧化膦用于合成25种不同的烯烃，收率高达97％。该方法具有良好的官能团耐受性，该反应可以从烷基氯化物，溴化物，或碘化物。另外，可以在使用2-MeTHF作为可再生溶剂的催化Wittig反应中使用聚（甲基氢硅氧烷）作为末端还原剂。Wittig反应的中间体通过31
• 2,3,4-substituted cyclopentanones as therapeutic agents
  申请人：Donde Yariv

  公开号：US20060111430A1

  公开（公告）日：2006-05-25

  Disclosed herein are compounds comprising or a pharmaceutically acceptable salt or a prodrug thereof; wherein Y, A, B, J, and E are further described. Methods, compositions, and medicaments related thereto are also disclosed.

  本文披露了包含Y、A、B、J和E的化合物，或其药学上可接受的盐或前药；还进一步描述了相关的方法、组合物和药物。
• Versatile palladium-catalyzed C–H olefination of (hetero)arenes at room temperature
  作者：Zhijie She、Yang Shi、Yumin Huang、Yangyang Cheng、Feijie Song、Jingsong You

  DOI：10.1039/c4cc05827e

  日期：——

  The room-temperature oxidative C–H/C–H cross-couplings between simple arenes and alkenes, coumarins or quinones have been reported by using a highly electrophilic palladium species [Pd(TFA)₂] as the catalyst and cheap (NH₄)₂S₂O₈ as the oxidant under air.

  室温下，使用高度亲电性的钯催化剂[Pd(TFA)₂]和廉价的(NH₄)₂S₂O₈氧化剂，在空气中报道了简单芳烃与烯烃、香豆素或喹喔啉之间的氧化C–H/C–H交叉偶联反应。
• An intramolecular Diels–Alder route to novel tetracyclic benzo[b]thiophene derivatives
  作者：Pilho Kim、Jennifer M. Tsuruda、Marilyn M. Olmstead、Shawn Eisenberg、Mark J. Kurth

  DOI：10.1016/s0040-4039(02)00565-8

  日期：2002.5

  A one-pot route to 3-benzo[b]thiophen-2-yl-acrylates (2) from the corresponding thiophenols (1) is reported. Ester reduction and subsequent hydroxyl esterification deliver psuedo trienoates (II) which undergo an intramolecular Diels–Alder (IMDA) reaction to give two 2-oxa-9-thiacyclopenta[b]fluoren-3-one products (I)—the major Diels–Alder product rearomatizes to 7.

  报道了从相应的苯酚（1）到3-苯并[ b ]噻吩-2-基丙烯酸酯（2）的一锅法。酯还原反应和随后的羟基酯化反应会生成伪三烯酸酯（II），其经过分子内Diels–Alder（IMDA）反应生成两种2-oxa-9-噻吩并环戊[ b ] fluoren -3-one产物（I）-主要Diels- der木产品重新定义为7。
• Efficient Synthesis of Acrylates Bearing an Aryl or Heteroaryl Moiety: One-Pot Method from Aromatics and Heteroaromatics Using Formylation and the Horner-Wadsworth-Emmons Reaction
  作者：Tatsuro Yasukata、Takaharu Matsuura

  DOI：10.3987/com-20-14400

  日期：——

  Acrylates bearing an aryl or heteroaryl moiety were efficiently prepared by a one-pot process employing a sequence of lithiation, formylation and the Horner-Wadsworth-Emmons reaction starting from aromatic and heteroaromatic compounds. This method can efficiently introduce an acrylate moiety into aromatic and heteroaromatic compounds.

  带有芳基或杂芳基部分的丙烯酸酯通过一锅法有效地制备，该一锅法使用一系列的锂化，甲酰化和霍纳-沃兹沃思-埃蒙斯反应，从芳族和杂芳族化合物开始。该方法可以有效地将丙烯酸酯部分引入芳族和杂芳族化合物中。