(+/-)-2-methyl-2H-tetrahydrothiopheneacetic acid | 139376-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: (+/-)-2-methyl-2H-tetrahydrothiopheneacetic acid
• 英文别名: 2-(2-methyltetrahydrothiophen-2-yl)acetic acid；2-(2-Methylthiolan-2-yl)acetic acid
• CAS: 139376-96-8
• 化学式: C₇H₁₂O₂S
• 分子量: 160.237
• InChiKey: SAAOGNSLESCZGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (+/-)-2-methyl-2H-tetrahydrothiopheneacetic acid 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 2-(2-methyltetrahydrothiophen-2-yl)ethanol
  参考文献：
  名称：

  [EN] NOVEL ORGANOLEPTIC COMPOUNDS AND THEIR USE IN FLAVOR AND FRAGRANCE COMPOSITIONS
  [FR] NOUVEAUX COMPOSÉS ORGANOLEPTIQUES ET LEUR UTILISATION DANS DES COMPOSITIONS D'ARÔME ET DE FRAGRANCE

  摘要：

  本发明涉及新型感官化合物，一种增强、提升或赋予口味的方法，选择的材料包括食品、口香糖、牙科产品、口腔卫生产品和药品，包括将这种新型感官化合物的嗅觉可接受量并入其中的步骤，以及通过添加这种新型感官化合物的嗅觉可接受量来改进、增强或修改香水组合的方法。

  公开号：

  WO2015157153A1
• 作为产物：
  描述：

  methyl (E)-6-iodo-3-methyl-2-hexenoate 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 32.0h， 生成 (+/-)-2-methyl-2H-tetrahydrothiopheneacetic 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

文献信息

• NOVEL COMPOUNDS FOR USE AS HIV PROTEASE INHIBITORS
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1339692A1

  公开（公告）日：2003-09-03
• NOVEL ORGANOLEPTIC COMPOUNDS AND THEIR USE IN FLAVOR AND FRAGRANCE COMPOSITIONS
  申请人：International Flavors & Fragrances Inc.

  公开号：EP3131889A1

  公开（公告）日：2017-02-22
• US6472404B1
  申请人：——

  公开号：US6472404B1

  公开（公告）日：2002-10-29
• [EN] NOVEL COMPOUNDS FOR USE AS HIV PROTEASE INHIBITORS<br/>[FR] NOUVEAUX COMPOSANTS SERVANT D'INHIBITEURS DE PROTEASE VIH
  申请人：HOFFMANN LA ROCHE

  公开号：WO2002042277A1

  公开（公告）日：2002-05-30

  Disclosed are compounds of general formula (I) and pharmaceutically acceptable salts thereof wherein R1 is H, hydroxy or NHR2 wherein R2 is H, alkyl, alkenyl, alkynyl, arylalkyl, heterocyclyalkyl, cycloalkyl, alkyl carbonyl, cycloalkyl carbonyl, aryl carbonyl, heterocyclyl carbonyl, aryl alkyl carbonyl, heterocyclyl alkyl carbonyl, alkyl oxy carbonyl, aryl alkyl oxy carbonyl, heterocyclyl alkyl oxy carbonyl, aryl heterocyclyl sulfonyl, alkyl sulfonyl, aryl sulfonyl, heterocyclyl sulfonyl or a group of formula (A) wherein X is O or S and R?7 and R8¿ independently are H, alkyl, aryl, heterocyclyl, aryl alkyl, heterocyclyl alkyl or R7 an R8 together with the notrogen atom to which they are attached form a saturated ring optionally containing a further hetero atom or a group (B) wherein when n=1, Y represents N, R9 is H or alkyl and R10 H, alkyl, aryl, alkyl, heterocyclyl alkyl, aryl, heterocyclyl or R?9 and R10¿ taken together with the hetero atom to which they are attached form a heterocycle R?11 and R12¿ independently are H or alkyl or R?11 and R12¿ taken together with the carbon atom to which they are attached form a cycle, R3, R4 independently are alkyl or taken together with the carbon atom to which they are attached form a carbocycle, R5 is alkyl, aryl alkyl, heterocyclyl alkyl or R?4 and R5¿ taken together with the carbon and sulfur atom to which they are attached form a heterocycle and R6 is alkyl, aryl alkyl, heterocyclyl alkyl, alkyl oxy alkyl, hydroxy alkyl, amino alkyl, fluoro alkyl and R13 is H or the residue of an inorganic ester and R15 is aryl, with the proviso that, if R?3, R4 and R5¿ are methyl, R6 is tert.butyl, R13 is H and if R15 is phenyl R2 is not benzyl oxycarbonyl and not 2-quinoline carbonyl. The compounds of formula (I) are potent inhibitors of the HIV aspartyl protease and can therefore be used in the treatment of HIV related diseases.
• Tandem SN2-Michael reactions for the preparation of simple five- and six-membered-ring nitrogen and sulfur heterocycles
  作者：Richard A. Bunce、Christopher J. Peeples、Paul B. Jones

  DOI：10.1021/jo00032a025

  日期：1992.3

  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.