2-(1-苯并噻吩-3-基)乙酸乙酯 | 7597-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 2-(1-苯并噻吩-3-基)乙酸乙酯
• 中文别名: 苯并[b]噻吩-3-乙酸乙酯
• 英文名称: ethyl benzothiophen-3-ylacetate
• 英文别名: ethyl 3-benzothienylacetate；ethyl 3-benzothiopheneacetate；ethyl 2-(benzothiophen-3-yl)acetate；benzo[b]thiophene-3-yl-acetic acid ethyl ester；ethyl(-1-benzothiophene-3-yl)acetate；ethyl benzo[b]thiene-3-acetate；ethyl benzo[b]thien-3-acetate；Ethyl 2-(1-benzothiophen-3-yl)acetate
• CAS: 7597-68-4
• 化学式: C₁₂H₁₂O₂S
• 分子量: 220.292
• InChiKey: QAJKYZFZTOKLRE-UHFFFAOYSA-N

物化性质

• 沸点：
  123-124 °C(Press: 0.3 Torr)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-(1-苯并噻吩-3-基)乙酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到2-benzo[b]thiophen-3-yl-ethanol
  参考文献：
  名称：

  Piperidinyl indole and tetrohydropyridinyl indole derivatives and method of their use

  摘要：

  3-哌啶基-1H-吲哚和3-(1,2,3,6-四氢吡啶-4-基)-1H-吲哚衍生物已被披露。还披露了使用这些衍生物以及含有这些衍生物的组合物在预防和/或治疗血清素紊乱，如抑郁症和焦虑症方面的方法。此外，还披露了制备3-哌啶基-1H-吲哚和3-(1,2,3,6-四氢吡啶-4-基)-1H-吲哚衍生物的方法。

  公开号：

  US20050004162A1
• 作为产物：
  描述：

  3-碘苯并[b]噻吩 在 sodium ethanolate 、 sodium hydride 、 copper(I) bromide 作用下， 反应 4.5h， 生成 2-(1-苯并噻吩-3-基)乙酸乙酯
  参考文献：
  名称：

  Cope rearrangements in the benzo[b]thiophene series

  摘要：

  The inability to observe Cope rearrangement products at elevated temperatures for diethyl alpha-allyl-2-naphthalenemalonate (1) and diethyl alpha-allyl-9-phenanthrenemalonate (2) does not extend to the analogous systems resulting from replacement of the aromatic units by 2- and 3-benzo[b]thiophene nuclei. Thermal rearrangement of diethyl alpha-allyl-3-benzo[b]thiophenemalonate (5) at 215-255-degrees-C for 11 h produces the expected Cope rearrangement product diethyl 2-allyl-3-benzo[b]thiophenemalonate (10) (8%) accompanied by trans- and cis-ethyl 2,3-dihydro-1-(ethoxycarbonyl)-1H-benzo-[b]cyclopenta[d]thiophene-2-acetate (9a) (10%) and (9b) (5%), respectively. The structure elucidation of 10, 9a, and 9b was done by spectroscopy. The attempted structure verification of 10 by an independent route gave diethyl 2-(1-propenyl)-3-benzo[b]thiophenemalonate (12) which when heated at 230-240-degrees-C for 18 h gave 1-carbethoxy-2-hydroxy-3-methyldibenzothiophene (16) as a major product. Similar results were observed with 2-substituted analogues of 5, both diethyl 3-allyl-2-benzo[b]thiophenemalonate (24) and ethyl 1,2-dihydro-3-(ethoxycarbonyl)-3H-benzo[b]cyclopenta-[d]thiophene-2-acetate (25) being formed. In this case the structure of 24 was verified by synthesis. An extension of this involved a study of thermal rearrangement of analogous compound ethyl alpha-allyl-alpha-cyano-3-benzo[b]thiopheneacetate (30). Thermal rearrangement of 30 at 235-245-degrees-C for 8 h gave the expected Cope rearrangement product ethyl alpha-cyano-2-allyl-3-benzo[b]thiopheneacetate (32) (6%) along with an unexpected diastereomeric mixture of 1-cyano-1-(ethoxycarbonyl)-2-methyl-2,3-dihydro-1H-benzo[b]cyclopenta[d]thiophenes(33)(18%). Speculative mechanistic considerations are offered regarding the mode of transformation of 12 to 16 and 32 to 33.

  DOI：

  10.1021/jo00068a034

文献信息

• Sulfoximidations of Benzylic C−H bonds by Photocatalysis
  作者：Han Wang、Duo Zhang、Carsten Bolm

  DOI：10.1002/anie.201801660

  日期：2018.5.14

  An efficient photocatalytic functionalization of compounds with benzylic C−H bonds by sulfoximidation in visible light is described. The mild reaction conditions allow the use of a broad array of substrates, including diarylmethane, alkyl arenes, arylacetonitrile, 2‐arylacetate, and alkynyl aryl methanes. The sulfoximidation process is highly chemoselective and leads to the corresponding sulfoximines

  描述了在可见光下通过亚磺酰亚胺化对具有苄基CH键的化合物进行的有效光催化功能化。温和的反应条件允许使用多种底物，包括二芳基甲烷，烷基芳烃，芳基乙腈，2-芳基乙酸酯和炔基芳基甲烷。亚磺酰亚胺化过程具有高度的化学选择性，并以通常良好的收率产生了相应的亚磺酰亚胺。机理研究表明，磺酰亚氨基自由基是中间的。
• Antidepressant 1-arylalkyl-4-(alkoxy pyridinyl)-and
  申请人：Bristol-Myers Squibb Company

  公开号：US05763444A1

  公开（公告）日：1998-06-09

  Novel compound of formula I and pharmaceutically acceptable salts thereof are useful CNS agents: ##STR1## wherein X is CH or N; X' is CH or a direct covalent link; Y is CH, CH.sub.2 or N; Y' is N, NH, O or S; R.sup.1 is H, Br, Cl, F, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkoxycarbonyl, CN, CONH.sub.2 or CH.sub.3 SO.sub.2 NH; n is 2 or 3; R.sup.2 is H or C.sub.1-4 alkyl; R.sup.3 is C.sub.1-4 alkoxy; R.sup.4 is H, Br, Cl, or F; and Z is CH or N.

  化合物I的新型化合物及其药学上可接受的盐是有用的中枢神经系统药物：##STR1## 其中X为CH或N；X'为CH或直接共价键；Y为CH、CH.sub.2或N；Y'为N、NH、O或S；R.sup.1为H、Br、Cl、F、C.sub.1-4烷基、C.sub.1-4烷氧基、C.sub.1-4烷氧羰基、CN、CONH.sub.2或CH.sub.3SO.sub.2NH；n为2或3；R.sup.2为H或C.sub.1-4烷基；R.sup.3为C.sub.1-4烷氧基；R.sup.4为H、Br、Cl或F；Z为CH或N。
• Antidepressant 1-arylalkyl-4-(alkoxypyridinyl)- or 4-(alkoxypyrimidinyl)piperazine derivatives
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0761666A3

  公开（公告）日：1998-01-28

  Novel compound of formula I and pharmaceutically acceptable salts thereof are useful CNS agents: wherein X is CH or N;X' is CH or a direct covalent link;Y is CH, CH2 or N;Y' is N, NH, O or S;R1 is H, Br, Cl, F, C1-4 alkyl, C1-4 alkoxy, C1-4 alkoxycarbonyl, CN, CONH2 or CH3SO2NH;n is 2 or 3;R2 is H or C1-4 alkyl;R3 is C1-4 alkoxy;R4 is H, Br, Cl, or F; andZ is CH or N.

  化合物I的新型化合物及其药用盐在中枢神经系统药物中有用：其中X为CH或N；X'为CH或直接共价键；Y为CH、CH2或N；Y'为N、NH、O或S；R1为H、Br、Cl、F、C1-4烷基、C1-4烷氧基、C1-4烷氧羰基、CN、CONH2或CH3SO2NH；n为2或3；R2为H或C1-4烷基；R3为C1-4烷氧基；R4为H、Br、Cl或F；Z为CH或N。
• Thiopyrano[1]benzothiophens. Synthesis of 1-phenyl-3H-thiopyrano-[3,4-b][1]benzothiophen-3-thione 9,9-dioxide and related compounds
  作者：Katherine Buggle、Úna Ní Ghógaín、Michael Nangle、Patrick MacManus

  DOI：10.1039/p19830001427

  日期：——

  The title compound (3a) was prepared by the reaction of 2-benzoylbenzo[b]thiophen-3(2H)-one 1,1-dioxide (1) with tetraphosphorus decasulphide, acetonitrile, and sodium hydrogen carbonate. The structure was confirmed by an alternative synthesis from ethyl 3-benzo[b]thienylacetate. The isomeric 4-phenyl-2H-thiopyrano[3,2-b][1]benzothiophen-2-thione 5,5-dioxide (2a) and a number of analogues of (3a) and

  通过使2-苯甲酰基苯并[ b ]噻吩-3（2H）-1，1，1-二氧化物（1）与十磷四磷，乙腈和碳酸氢钠反应制备标题化合物（3a）。通过3-苯并[ b ]噻吩基乙酸乙酯的另一合成方法证实了该结构。制备了4-苯基-2 H-硫代吡喃并[3，2- b ] [1]苯并噻吩-2-硫酮5，5-二氧化物的异构体（2a）以及许多类似物（3a）和（2a）。
• π‐Conjugated Organic–Inorganic Hybrid Photoanodes: Revealing the Photochemical Behavior through In Situ X‐Ray Absorption Spectroscopy
  作者：Chia‐Shuo Hsu、Marek K. Węcławski、Beata Koszarna、Daniel T. Gryko、Hao Ming Chen

  DOI：10.1002/chem.201804829

  日期：2018.12.10

  energy level of the LUMO and the photoinduced charge‐carrier‐transfer efficiency to be modulated. X‐Ray absorption near‐edge structure (XANES) spectroscopy confirmed that the charge transfer is a crucial factor contributing to the resulting activity of the photoanode. The photoactivity of the photoanodes towards water oxidation was revealed to be governed by both the LUMO energy level and transfer efficiency

  小分子有机半导体由于其n型半导体性质和可调节的带隙而在水的光电化学氧化中显示出巨大的潜力。在这项工作中，合成了几种头尾双香豆素，并表征了它们的光物理性质。通过改变位置1和7上取代基的电子特性，可以改变其作为n型半导体的特性，从而可以调节LUMO的能级和光致电荷载流子转移效率。X射线吸收近边缘结构（XANES）光谱证实，电荷转移是导致光电阳极活性的关键因素。揭示了光阳极对水氧化的光活性受LUMO能级和光诱导电荷载流子的转移效率的支配。在研究的分子中，具有苯并噻吩基取代基的双香豆素作为光电化学水氧化的光吸收剂显示出最大的潜力。