(+/-)-1,3-dihydrobenzothiophene-1-acetic acid | 139376-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异硫色满
• 英文名称: (+/-)-1,3-dihydrobenzothiophene-1-acetic acid
• 英文别名: 2-(1,3-Dihydro-2-benzothiophen-1-yl)acetic acid
• CAS: 139376-89-9
• 化学式: C₁₀H₁₀O₂S
• 分子量: 194.254
• InChiKey: UDXJVIUGFPRYOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-1,3-dihydrobenzothiophene-1-acetic acid 在 sodium hydroxide 、 sodium periodate 、 三氟甲磺酸酐 、 四丁基硫酸氢铵 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 indolo<2,1-b><1,3>benzothiazonin-9(2H)-one
  参考文献：
  名称：

  A Sulfoxide-Based Ring Annelation Approach to Fused, Many-Membered Ring N,S-Heterocycles¹

  摘要：

  An approach to many-membered ring N,S-heterocycles involving sulfoxide electrophilic sulfenylation (SES followed by ring expansion of the derived sulfonium salt intermediate tin situ) is illustrated for 9- and 10-membered-ring compounds. Treatment of readily prepared sulfoxides 10a, 10b, 18a, 18b, 23a, and 23b with triflic anhydride (pyridine, CH2Cl2, 0 degrees C) provides heterocycles 13a (65%), 13b (60%), 19a (67%), 19b (67%), 24a (42%), and 24b (80%), respectively. Sulfoxides 5a and 5b, under several different conditions, give only the Pummerer dehydration products 6a and 6b, respectively. Diastereomeric sulfoxides 18a' and 18b', upon treatment with triflic anhydride, do not produce clean product mixtures or any of the desired heterocyclic products but, upon heating in toluene, are converted to the more stable isomers 18a and 18b, respectively. Conducting this isomerization in the presence of 2-mercaptobenzothiazole produces a disulfide indicative of the intermediacy of a sulfenic acid. However, the importance of sulfenic acid derivatives in the SES process leading to many-membered ring heterocycles remains to be determined.

  DOI：

  10.1021/jo9805044
• 作为产物：
  描述：

  (E)-3-(2-Carbamimidoylsulfanylmethyl-phenyl)-acrylic acid ethyl ester; hydrobromide 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 8.0h， 以69%的产率得到(+/-)-1,3-dihydrobenzothiophene-1-acetic acid
  参考文献：
  名称：

  Tandem SN2-Michael reactions for the preparation of simple five- and six-membered-ring nitrogen and sulfur heterocycles

  摘要：

  A one-pot tandem S(N)2-Michael addition sequence has been developed for the preparation of five-membered- and six-membered-ring nitrogen and sulfur heterocycles from 6- or 7-halo-2-alkenoate esters. Nitrogen-containing rings are prepared by reaction of the omega-halo-2-alkenoate ester with a primary amine in the presence of triethylamine. The sulfur analogues are generated by thiourea displacement of the halide followed by base hydrolysis of the isothiouronium salt. Yields are routinely in the 60-80% range. Experiments are described which elucidate the chronology of the reaction sequences. Ring size and steric hindrance to the initial substitution reaction appear to be the only limitations of the procedure.

  DOI：

  10.1021/jo00032a025