6,7-dihydro-5H-benzo[b]thiophene-4-one oxime | 19995-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 6,7-dihydro-5H-benzo[b]thiophene-4-one oxime
• 英文别名: 4,5,6,7-tetrahydro-4-oxobenzo[b]thiophene oxime；6,7-dihydro-4-benzo[b]thiophenone oxime；6,7-dihydro-5H-benzo[b]thiophen-4-one oxime；6,7-Dihydro-5H-benzo[b]thiophen-4-on-oxim；4-Oximino-4,5,6,7-tetrahydrothianaphthene；N-(6,7-dihydro-5H-1-benzothiophen-4-ylidene)hydroxylamine
• CAS: 19995-19-8；79222-03-0；79222-05-2
• 化学式: C₈H₉NOS
• mdl: MFCD00182862
• 分子量: 167.232
• InChiKey: JMHKHQOLEYGCNT-UHFFFAOYSA-N

物化性质

• 熔点：
  131-132 °C
• 沸点：
  333.4±21.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  6,7-dihydro-5H-benzo[b]thiophene-4-one oxime 在 镍 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (1R,2R)-2-乙基环己烷-1-胺
  参考文献：
  名称：

  Preparation of primary aliphatic and alicyclic amines from thiophene derivatives

  摘要：

  DOI：

  10.1007/bf00920270
• 作为产物：
  描述：

  4-(2-噻吩基)丁酰氯 在 三氯化铝 、 羟胺 作用下， 生成 6,7-dihydro-5H-benzo[b]thiophene-4-one oxime
  参考文献：
  名称：

  Cagniant; Cagniant, Bulletin de la Societe Chimique de France, 1953, p. 62,68, 713, 717

  摘要：

  DOI：

文献信息

• Regioselective Synthesis of Heterocycles Containing Nitrogen Neighboring an Aromatic Ring by Reductive Ring Expansion Using Diisobutylaluminum Hydride and Studies on the Reaction Mechanism
  作者：Hidetsura Cho、Yusuke Iwama、Kenji Sugimoto、Seiji Mori、Hidetoshi Tokuyama

  DOI：10.1021/jo902177p

  日期：2010.2.5

  including indoline, 1,2,3,4,5,6-hexahydrobenz[b]azocine, 3,4-dihydro-2H-benzo[b][1,4]oxazine, 2,3,4,5-tetrahydrobenzo[b][1,4]thiazepine, 1,2,3,4,5,6-hexahydroazepino[3,2-b]indole, 2,3,4,5-tetrahydro-1H-benzothieno[2,3-b]azepine, 2,3,4,5-tetrahydro-1H-benzothieno[3,2-b]azepine, 5,6-dihydrophenanthridine, and 5,6,11,12-tetrahydrodibenz[b, f]azocine. The reaction mechanism leading to the rearrangement was

  描述了与二异丁基氢化铝（DIBALH）稠合到芳环上的环状酮肟的还原扩环反应的系统研究。该反应区域选择性地提供了多种五至八元双环杂环或三环杂环，其包含与芳香环相邻的氮，包括二氢吲哚，1,2,3,4,5,6-六氢苯并[ b ]偶氮辛，3,4-二氢-2 H-苯并[ b ] [1,4]恶嗪，2,3,4,5-四氢苯并[ b ] [1,4]噻氮平，1,2,3,4,5,6-六氢氮庚啶[3 ，2- b ]吲哚，2,3,4,5-四氢-1 H-苯并噻吩并[2,3- b ]氮杂，2,3,4,5-四氢-1 H-苯并噻吩并[3,2- b]氮杂，5,6-二氢菲啶和5,6,11,12-四氢二苯并[ b，f ]偶氮星。基于受限的Becke三参数加Lee-Yang-Parr（B3LYP）密度泛函理论（DFT）和6-31G（d）基础集，研究了导致重排的反应机理。发现该反应通过逐步机理通过三中心过渡态进行，因为沿着本征反应坐标
• The synthesis and vasopressin (AVP) antagonist activity of a novel series of n -aroyl-2,4,5,6-tetrahydropyrazolo [3,4- d ]thieno[3,2- b ]azepines
  作者：J.Donald Albright、Efren G.Delos Santos、John P Dusza、Peter S Chan、Joseph Coupet、Xun Ru、H Mazandarani

  DOI：10.1016/s0960-894x(00)00084-6

  日期：2000.4

  Synthesis and SAR of N-[4-[(4,5-dihydropyrazolo[3,4-d]thieno[3,2-b]azepin-6(2H)-y l)carbonyl]phenyl]benzamides as arginine vasopressin (AVP) receptor antagonists are discussed. Potent orally active AVP receptor antagonists are produced when the benzamide moiety contains a phenyl group at the 2-position. Similar analogues of 4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepine and VPA-985 are reported.

  N- [4-[（4,5-二氢吡唑并[3,4-d]噻吩并[3,2-b] a嗪-6（2H）-基）羰基]苯基]苯甲酰胺为精氨酸加压素（AVP）的合成和SAR讨论了受体拮抗剂。当苯甲酰胺部分在2位上含有苯基时，会产生有效的口服活性AVP受体拮抗剂。据报道有4,6,7,8-四氢-5H-噻吩并[3,2-b]氮杂和VPA-985的类似物。
• Synthesis of <i>N</i>-Trifluoromethanesulfinyl Ketimines by Cascade Trifluoromethylthiolation/Rearrangement of Ketoximes
  作者：Bora Kim、Junho Park、Chang-Woo Cho

  DOI：10.1021/acs.orglett.1c01338

  日期：2021.6.18

  A new and efficient cascade electrophilic trifluoromethylthiolation/radical rearrangement reaction of ketoximes is reported using N-trifluoromethylthio-dibenzenesulfonimide as the SCF3 source without any additives. This simple one-pot reaction provides the corresponding N-trifluoromethanesulfinyl ketimine products in good yields with high E selectivity under mild reaction conditions.

  报道了使用N-三氟甲硫基二苯磺酰亚胺作为 SCF 3源而没有任何添加剂的酮肟的新型高效级联亲电三氟甲硫基化/自由基重排反应。这种简单的一锅反应在温和的反应条件下以良好的收率和高E选择性提供了相应的N-三氟甲亚磺酰基酮亚胺产物。
• Ring-Expansion Reaction of Oximes with Aluminum Reductants
  作者：Hidetsura Cho、Yusuke Iwama、Nakako Mitsuhashi、Kenji Sugimoto、Kentaro Okano、Hidetoshi Tokuyama

  DOI：10.3390/molecules17067348

  日期：——

  The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl2, AlH3 (alane), LiAlH4, LiAlH(OtBu)3, and (MeOCH2CH2O)2AlH2Na (Red-Al) were examined. Among reductants, AlHCl2 (LiAlH4:AlCl3 = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained

  研究了杂环酮肟和碳环酮肟与几种还原剂如 AlHCl2、AlH3（铝烷）、LiAlH4、LiAlH(OtBu)3 和 (MeOCH2CH2O)2AlH2Na（Red-Al）的扩环反应。在还原剂中，环戊基甲基醚 (CPME) 中的 AlHCl2 (LiAlH4:AlCl3 = 1:3) 已被发现是适合该反应的试剂，并且重排的环状仲胺以良好到极好的收率获得。
• Biphenyl vasopressin agonists
  申请人：Failli A. Amedeo

  公开号：US20050075328A1

  公开（公告）日：2005-04-07

  A compound of the formulae (I) or (II): wherein: Y is a moiety selected from NR or —(CH 2 ) n ; wherein R is hydrogen or (C 1 -C 6 ) lower alkyl, and n is 1; represents: (1) a phenyl ring optionally substituted with one or two substituents selected, independently, from the group comprising hydrogen, (C 1 -C 6 ) lower alkyl, halogen, cyano, CF 3 , hydroxy, (C 1 -C 6 ) lower alkoxy, (C 1 -C 6 ) lower alkoxy carbonyl, carboxy, —CONH 2 , —CONH[(C 1 -C 6 ) lower alkyl], —CON[(C 1 -C 6 ) lower alkyl] 2 ; or (2) a 6-membered aromatic (unsaturated) heterocyclic ring having one nitrogen atom, optionally substituted by (C 1 -C 6 ) lower alkyl, halogen or (C 1 -C 6 ) lower alkoxy; represents: (1) a phenyl ring optionally substituted with one or two substituents selected, independently, from the group comprising hydrogen, (C 1 -C 6 ) lower alkyl, halogen, cyano, CF 3 , hydroxy, (C 1 -C 6 ) lower alkoxy, or (C 1 -C 6 ) lower alkoxy carbonyl, carboxy, —CONH 2 , —CONH[(C 1 -C 6 ) lower alkyl], —CON[(C 1 -C 6 ) lower alkyl] 2 ; or (2) a 5-membered aromatic (unsaturated) heterocyclic ring having one nitrogen atom, optionally substituted by (C 1 -C 6 ) lower alkyl, (C 1 -C 6 ) lower alkoxy, or halogen; or (3) a 6-membered aromatic (unsaturated) heterocyclic ring having one nitrogen atom, optionally substituted by (C 1 -C 6 ) lower alkyl, halogen, or (C 1 -C 6 ) lower alkoxy; represents a 5-membered aromatic (unsaturated) heterocyclic ring having one sulfur atom, optionally substituted by (C 1 -C 6 ) lower alkyl, halogen, or (C 1 -C 6 ) lower alkoxy; R 1 is a moiety of the formula and R 2 , R 3 , R 7 , R 8 and R 9 are, independently, selected from a group consisting of hydrogen, (C 1 -C 3 ) lower alkyl, OCH 3 , halogen, CF 3 , —SCH 3 , OCF 3 , SCF 3 , or CN; or a pharmaceutically acceptable salt, or pro-drug form thereof.

  化合物的化学式为(I)或(II)，其中：Y是选自NR或—(CH2)n的基团；其中R是氢或(C1-C6)低级烷基，n为1；表示为：(1)苯环，可选地取代有一个或两个取代基，所述取代基独立地选自氢、(C1-C6)低级烷基、卤素、氰、CF3、羟基、(C1-C6)低级烷氧基、(C1-C6)低级烷氧基羰基、羧基、—CONH2、—CONH[(C1-C6)低级烷基]、—CON[(C1-C6)低级烷基]2；或(2)具有一个氮原子的6元芳香(不饱和)杂环，可选地取代有(C1-C6)低级烷基、卤素或(C1-C6)低级烷氧基；表示为：(1)苯环，可选地取代有一个或两个取代基，所述取代基独立地选自氢、(C1-C6)低级烷基、卤素、氰、CF3、羟基、(C1-C6)低级烷氧基或(C1-C6)低级烷氧基羰基、羧基、—CONH2、—CONH[(C1-C6)低级烷基]、—CON[(C1-C6)低级烷基]2；或(2)具有一个氮原子的5元芳香(不饱和)杂环，可选地取代有(C1-C6)低级烷基、(C1-C6)低级烷氧基或卤素；或(3)具有一个氮原子的6元芳香(不饱和)杂环，可选地取代有(C1-C6)低级烷基、卤素或(C1-C6)低级烷氧基；表示为具有一个硫原子的5元芳香(不饱和)杂环，可选地取代有(C1-C6)低级烷基、卤素或(C1-C6)低级烷氧基；R1是如下式的基团，其中R2、R3、R7、R8和R9独立地选自氢、(C1-C3)低级烷基、OCH3、卤素、CF3、—SCH3、OCF3、SCF3或CN；或其药学上可接受的盐或前药形式。