2,3,4,5-tetrahydrothiophene-2-acetamide | 219532-33-9

• 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: 2,3,4,5-tetrahydrothiophene-2-acetamide
• 英文别名: 2-(Thiolan-2-yl)acetamide
• CAS: 219532-33-9
• 化学式: C₆H₁₁NOS
• mdl: MFCD19216091
• 分子量: 145.225
• InChiKey: DFNYVEOSGGUJKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetrahydrothiophene-2-acetamide 在 sodium periodate 作用下， 以 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 44.0h， 生成 1-<(2,3,4,5-tetrahydro-2-thienyl)acetyl>-1H-pyrrole 1-oxide
  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：

  tetrahydrothiophene-2-acetylchloride 在 ammonium hydroxide 作用下， 以84%的产率得到2,3,4,5-tetrahydrothiophene-2-acetamide
  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

文献信息

• FUSED HETEROCYCLE DERIVATIVES AND USE THEREOF
  申请人：OGURO Yuya

  公开号：US20090163488A1

  公开（公告）日：2009-06-25

  A compound represented by the formula (I): wherein Z 1 , Z 2 , Z 3 and Z 4 are the following combination, (Z 1 ,Z 2 ,Z 3 ,Z 4 )=(CR 4 ,N,CR 5 ,C), (N,N,CR 5 ,C), (N,C,CR 5 ,N), (S,C,CR 5 ,C) or (S,C,N,C); R 1 and R 2 are the same or different and each is (1) a hydrogen atom, (2) a halogen atom, (3) a group bonded via a carbon atom, (4) a group bonded via a nitrogen atom, (5) a group bonded via an oxygen atom or (6) a group bonded via a sulfur atom; R 3 is an amino optionally having substituent(s); R 4 and R 5 are the same or different and each is (1) a hydrogen atom, (2) a halogen atom, (3) a group bonded via a carbon atom, (4) a group bonded via a nitrogen atom, (5) a group bonded via an oxygen atom or (6) a group bonded via a sulfur atom; R 3 and R 4 optionally form a ring optionally having substituent(s); and a group represented by the formula is a cyclic group optionally having substituent(s), or a salt thereof.

  化合物的分子式为（I）：其中Z1，Z2，Z3和Z4是以下组合，（Z1，Z2，Z3，Z4）=（CR4，N，CR5，C），（N，N，CR5，C），（N，C，CR5，N），（S，C，CR5，C）或（S，C，N，C）; R1和R2相同或不同，每个都是（1）氢原子，（2）卤原子，（3）通过碳原子键合的基团，（4）通过氮原子键合的基团，（5）通过氧原子键合的基团或（6）通过硫原子键合的基团; R3是氨基，可以有取代基; R4和R5相同或不同，每个都是（1）氢原子，（2）卤原子，（3）通过碳原子键合的基团，（4）通过氮原子键合的基团，（5）通过氧原子键合的基团或（6）通过硫原子键合的基团; R3和R4可以选择形成一个环，也可以有取代基; 以及由公式表示的基团是一个环状基团，可以有取代基，或其盐。
• HETEROBICYCLIC COMPOUNDS AS KINASE INHIBITORS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2162445A1

  公开（公告）日：2010-03-17
• US8304557B2
  申请人：——

  公开号：US8304557B2

  公开（公告）日：2012-11-06
• [EN] HETEROBICYCLIC COMPOUNDS AS KINASE INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROBICYCLIQUES COMME INHIBITEURS DE KINASE
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2008150015A1

  公开（公告）日：2008-12-11

  [EN] A compound represented by the formula (I): wherein Z1, Z2, Z3 and Z4 are the following combination, (Z1,Z2,Z3,Z4)=(CR4,N,CR5,C), (N,N,CR5,C), (N,C,CR5,N), (S,C,CR5,C) or (S,C,N,C); R1 and R2 are the same or different and each is (1) a hydrogen atom, (2) a halogen atom, (3) a group bonded via a carbon atom, (4) a group bonded via a nitrogen atom, (5) a group bonded via an oxygen atom or (6) a group bonded via a sulfur atom; R3 is an amino optionally having substituent(s); R4 and R5 are the same or different and each is (1) a hydrogen atom, (2) a halogen atom, (3) a group bonded via a carbon atom, (4) a group bonded via a nitrogen atom, (5) a group bonded via an oxygen atom or (6) a group bonded via a sulfur atom; R3 and R4 optionally form a ring optionally having substituent(s); and a group represented by the formula (A) is a cyclic group optionally having substituent(s), or a salt thereof.
  [FR] L'invention porte sur un composé représenté par la formule (I) : dans laquelle Z1, Z2, Z3 et Z4sont la combinaison suivante, (Z1,Z2,Z3,Z4) = (CR4,N,CR5,C), (N,N,CR5,C), (N,C,CR5,N), (S,C,CR5,C) ou (S,C,N,C); R1 et R2 sont identiques ou différents et chacun représente (1) un atome d'hydrogène, (2) un atome d'halogène, (3) un groupe lié par l'intermédiaire d'un atome de carbone, (4) un groupe lié par l'intermédiaire d'un atome d'azote, (5) un groupe lié par l'intermédiaire d'un atome d'oxygène ou (6) un groupe lié par l'intermédiaire d'un atome de soufre ; R3 est un amino ayant facultativement un ou des substituants ; R4 et R5 sont identiques ou différents et représentent chacun (1) un atome d'hydrogène, (2) un atome d'halogène, (3) un groupe lié par l'intermédiaire d'un atome de carbone, (4) un groupe lié par l'intermédiaire d'un atome d'azote, (5) un groupe lié par l'intermédiaire d'un atome d'oxygène ou (6) un groupe lié par l'intermédiaire d'un atome de soufre ; R3 et R4 forment facultativement un cycle ayant facultativement un ou des substituants ; et un groupe représenté par la formule (A) est un groupe cyclique ayant facultativement un ou des substituants. L'invention porte également sur un sel de ce composé.
• A Sulfoxide-Based Ring Annelation Approach to Fused, Many-Membered Ring <b><i>N</i></b>,<b><i>S</i></b>-Heterocycles¹
  作者：Dallas K. Bates、Mingde Xia

  DOI：10.1021/jo9805044

  日期：1998.12.1

  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.