ethyl 2-benzothiopheneacetate | 128405-96-9

• 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: ethyl 2-benzothiopheneacetate
• 英文别名: ethyl benzothiophen-2-ylacetate；benzo[b]thiophen-2-yl-acetic acid ethyl ester；Benzo[b]thiophen-2-yl-essigsaeure-aethylester；Ethyl 2-(1-benzothiophen-2-yl)acetate
• CAS: 128405-96-9
• 化学式: C₁₂H₁₂O₂S
• 分子量: 220.292
• InChiKey: FVVOKLWLHMGWLJ-UHFFFAOYSA-N

物化性质

• 沸点：
  150 °C(Press: 2 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：

  ethyl 2-benzothiopheneacetate 在 sodium hydroxide 作用下， 生成 苯并[b]噻吩-2-乙酸
  参考文献：
  名称：

  噻吨的衍生物。

  摘要：

  DOI：

  10.1021/ja01191a066
• 作为产物：
  描述：

  diethyl α-acetoxy-2-benzothiophenemalonate 在 sodium ethanolate 、 sodium naphthalenide 作用下， 以 六甲基磷酰三胺 、 苯 为溶剂， 反应 4.5h， 生成 ethyl 2-benzothiopheneacetate
  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

• Rh(<scp>ii</scp>)/phosphine-cocatalyzed synthesis of dithioketal derivatives from diazo compounds through simultaneous construction of two different C–S bonds
  作者：Changqing Rao、Shaoyu Mai、Qiuling Song

  DOI：10.1039/c8cc01656a

  日期：——

  Rhodium(II)/phosphine-cocatalyzed bis-sulfuration of α-diazocarbonyl compounds using thiosulfonates as the sulfenylating agent, which provided two sulfur-containing moieties, was developed via simultaneous inter- and intra-molecular C–S bond formation. This novel protocol provides a rapid synthetic route to dithioketal derivatives in moderate to good yields in an atom-economic process. The transformation

  铑（Ⅱ）/膦用硫代磺酸盐作为亚磺酰化剂对α-重氮羰基化合物的双硫化双硫化，通过同时形成分子间和分子内CS键而形成，提供了两个含硫部分。该新方案为原子经济过程中中等至良好的产率提供了快速合成二硫代缩酮衍生物的途径。有人建议通过膦叶立德的形成，然后进行S（O 2）-S键的裂解和重排来进行转化。
• Process for the preparation of graft copolymers by Reversible Addition Fragmentation Chain Transfer (RAFT) and Ring Opening Polymerisation (ROP)
  申请人：Polymers Australia PTY Limited

  公开号：EP1950232A1

  公开（公告）日：2008-07-30

  A combined RAFT/ROP process for the preparation of a graft co-polymer having a backbone built-up from repeating units derived by polymerization of free-radically polymerizable monomers comprising vinylic monomers, and polyester side chains grafted to said backbone derived by ring-opening polymerisation of cyclic ester compounds; said process comprising reacting a mixture of (a) one or more vinylic monomers, optionally in combination with other monomers susceptible to free-radical polymerization, wherein at least one of said vinylic monomers comprises a (free) hydroxyl group; (b) a thiocarbonylthio compound as chain transfer agent; (c) one or more cyclic esters, which is/are susceptible to a ring-opening polymerization; and (d) a compound effective for initiating the ring-opening polymerization of the one or more cyclic esters; and reacting said mixture in an inert solvent at a temperature of more than 90°C under exclusion of oxygen to form the graft copolymer.

  一种结合了RAFT/ROP过程的方法，用于制备一种接枝共聚物，其骨架由通过自由基聚合获得的重复单元构建，包括乙烯单体，并且由环酯化合物的环开聚合衍生的聚酯侧链嫁接到该骨架上；该方法包括反应以下混合物：(a) 一种或多种乙烯单体，可选地与其他易于自由基聚合的单体组合在一起，其中至少一种乙烯单体包含一个（自由）羟基；(b) 一种硫代羰基硫化合物作为链转移剂；(c) 一种或多种易于环开聚合的环酯；以及(d) 一种有效于启动一种或多种环酯的环开聚合的化合物；并在惰性溶剂中，在排除氧气的条件下，以高于90°C的温度反应该混合物，以形成接枝共聚物。
• Process for preparing polyolefins
  申请人：Nippon Petrochemicals Co., Ltd.

  公开号：EP0267794A2

  公开（公告）日：1988-05-18

  A process for preparing a polyolefin by homopolymerizing or copolymerizing an olefin or olefins using a catalyst comprising a solid catalyst component and an organometallic compound, said solid catalyst component being obtained by contacting at least a titanium compound and/or a vanadium compound with a solid material (a), said solid material (a) being obtained by contacting the following components (1), (2) and (3) with one another: (1) a silicon oxide and/or an aluminum oxide, (2) a magnesium halide, and (3) an organometallic compound.

  一种使用由固体催化剂组分和有机金属化合物组成的催化剂，通过均聚或共聚一种或多种烯烃制备聚烯烃的工艺，所述固体催化剂组分通过将至少一种钛化合物和/或钒化合物与固体材料（a）接触而获得，所述固体材料（a）通过将以下组分（1）、（2）和（3）相互接触而获得：（1）氧化硅和/或氧化铝，（2）卤化镁，和（3）有机金属化合物。
• Jackson, P. Mark; Moody, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1990, p. 681 - 687
  作者：Jackson, P. Mark、Moody, Christopher J.

  DOI：——

  日期：——
• JACKSON, P. MARK;MOODY, CHRISTOPHER J., J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 681-687
  作者：JACKSON, P. MARK、MOODY, CHRISTOPHER J.

  DOI：——

  日期：——