2-methoxydibenzocyclohepten-5-one | 42982-04-7

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 2-methoxydibenzocyclohepten-5-one
• 英文别名: 2-methoxy-5H-dibenzo[a,d]cyclohepten-5-one；6-Methoxytricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-2-one
• CAS: 42982-04-7
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: WGDWRKWHFLZCCL-UHFFFAOYSA-N

物化性质

• 沸点：
  421.6±44.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methoxydibenzocyclohepten-5-one 在 sodium hydroxide 、 三氯化铝 、 potassium tert-butylate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.08h， 生成 5-<(5-Oxo-dibenzocyclohepten-2-yl)oxy>valeric acid
  参考文献：
  名称：

  Synthesis of 5-(((R,S)-5-((9-Fluorenylmethoxycarbonyl)amino)-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl)oxy)valeric Acid (CHA) and 5-(((R,S)-5-((9-Fluorenylmethoxycarbonyl)amino)dibenzo[a,d]-cyclohepten-2-yl)oxy)valeric Acid (CHE) Handles for the Solid-Phase Synthesis of C-Terminal Peptide Amides under Mild Conditions

  摘要：

  Two novel handles for peptide amide preparation under mild conditions were developed for use in highly efficient solid-phase peptide synthesis. These handles, 5-{[(R,S)-5-[(9-fluorenylmethoxy-carbonyl)amino]-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl]oxy}valeric acid (CHA) and 5-{[(R,S)-5-[(9-fluorenylmethoxycarbonyl)amino]dibenzo[a,d]cyclohepten-2-yl]oxy}valeric acid (CHE), were attached to the solid support and were used for syntheses of peptides having a C-terminal amide by the fluorenylmethoxycarbonyl strategy. The cleavability of CHA and CHE was determined and compared with the that commercially available amide handles. CHA and CHE handles can be rapidly cleaved from the polymer support without significant side reactions using lower acid concentrations than those required for conventional handles. As CHA can be easily synthesized in large amounts, it is suitable for peptide amide preparation for pharmaceuticals. As CHE can be cleaved at very low concentrations of acid, it is especially suitable for preparing side chain-protected peptide amides: Several brain-gut peptides having a C-terminal amide were synthesized in high yield and high purity with these novel handles.

  DOI：

  10.1021/jo00105a010
• 作为产物：
  描述：

  3-甲氧基苯乙酸 在 W-2 Raney Ni N-溴代丁二酰亚胺(NBS) 、 TEA 、 氢气 、 sodium acetate 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 50.0~245.0 ℃ 、392.24 kPa 条件下， 反应 68.83h， 生成 2-methoxydibenzocyclohepten-5-one
  参考文献：
  名称：

  Synthesis of 5-(((R,S)-5-((9-Fluorenylmethoxycarbonyl)amino)-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl)oxy)valeric Acid (CHA) and 5-(((R,S)-5-((9-Fluorenylmethoxycarbonyl)amino)dibenzo[a,d]-cyclohepten-2-yl)oxy)valeric Acid (CHE) Handles for the Solid-Phase Synthesis of C-Terminal Peptide Amides under Mild Conditions

  摘要：

  Two novel handles for peptide amide preparation under mild conditions were developed for use in highly efficient solid-phase peptide synthesis. These handles, 5-{[(R,S)-5-[(9-fluorenylmethoxy-carbonyl)amino]-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl]oxy}valeric acid (CHA) and 5-{[(R,S)-5-[(9-fluorenylmethoxycarbonyl)amino]dibenzo[a,d]cyclohepten-2-yl]oxy}valeric acid (CHE), were attached to the solid support and were used for syntheses of peptides having a C-terminal amide by the fluorenylmethoxycarbonyl strategy. The cleavability of CHA and CHE was determined and compared with the that commercially available amide handles. CHA and CHE handles can be rapidly cleaved from the polymer support without significant side reactions using lower acid concentrations than those required for conventional handles. As CHA can be easily synthesized in large amounts, it is suitable for peptide amide preparation for pharmaceuticals. As CHE can be cleaved at very low concentrations of acid, it is especially suitable for preparing side chain-protected peptide amides: Several brain-gut peptides having a C-terminal amide were synthesized in high yield and high purity with these novel handles.

  DOI：

  10.1021/jo00105a010

文献信息

• Substituted 9-Anthraldehydes from Dibenzocycloheptanol Epoxides via Acid-Catalyzed Epoxide Opening/Semipinacol Rearrangement
  作者：Tanawat Phumjan、Poramate Songthammawat、Jira Jongcharoenkamol、Paratchata Batsomboon、Somsak Ruchirawat、Poonsakdi Ploypradith

  DOI：10.1021/acs.joc.1c01405

  日期：2021.10.1

  decomposition during the epoxidation. From the mechanistic studies, the semipinacol rearrangement of the epoxide could precede the ionization at the bisbenzylic position, yielding the aldehyde intermediate. The ensuing dehydrative aromatization led to the formation of 9-anthraldehyde. Conversely, nucleophilic addition to the aldehyde and dehydrative aromatization with concomitant loss of formic acid

  以苯甲醛衍生物为原料，可以分五步制备相应的二苯并环庚烯醇。在两种底物（仲醇与叔醇和芳环上的取代基）和条件控制下，随后的环氧化和酸催化的环氧化物开环/半频哪醇重排/芳构化以良好的收率提供了相应的 9-蒽醛，高达 88 % 分两步。芳环上吸电子基团的存在抑制了环氧化速率，而随后的半频哪醇重排步骤需要加热；另一方面，给电子基团的存在经常导致环氧化过程中的分解。从机理研究来看，环氧化物的半频哪醇重排可以先于双苄基位置的电离，产生醛中间体。随后的脱水芳构化导致9-蒽醛的形成。相反，醛的亲核加成和脱水芳构化伴随着甲酸的损失导致蒽。
• Tandem Oxidative Ring Expansion for Synthesis of Dibenzocyclooctaphenanthrenes
  作者：Lu Yang、Hidenori Matsuyama、Sheng Zhang、Masahiro Terada、Tienan Jin

  DOI：10.1021/acs.orglett.0c01725

  日期：2020.7.2

  A novel tandem single-electron oxidative ring expansion reaction has been developed for the construction of the saddle-shaped polycyclic arenes fused with cyclooctatetraene, that is, dibenzo[3,4:7,8]cycloocta[1,2-l]phenanthrenes (dbCOTPs). The combination of Cu(OTf)2 catalyst with DDQ triggered the selective oxidation of o-biphenyl-tethered methylenecirculenes fused with a seven-membered ring, giving

  已经开发了一种新颖的串联单电子氧化环扩环反应，用于构建与环辛酸酯，即二苯并[3,4：7,8]环辛[1,2- l ]菲（ dbCOTP）。Cu（OTf）2催化剂与DDQ的结合触发了与七元环稠合的邻联苯系留亚甲基环的选择性氧化，从而形成了相应的八元环稠合的dbCOTP。当前的七元环到八元环的串联扩环是通过亚苄基部分的选择性单电子氧化，分子内螺环化和1,2-芳基迁移序列发生的。
• Development of Novel Inhibitors for Histone Methyltransferase SET7/9 based on Cyproheptadine
  作者：Tomoya Hirano、Takashi Fujiwara、Hideaki Niwa、Michitake Hirano、Kasumi Ohira、Yusuke Okazaki、Shin Sato、Takashi Umehara、Yuki Maemoto、Akihiro Ito、Minoru Yoshida、Hiroyuki Kagechika

  DOI：10.1002/cmdc.201800233

  日期：2018.8.10

  considered candidates for the treatment of diseases. Previously, our group identified cyproheptadine, used clinically as a serotonin receptor antagonist and histamine receptor (H1) antagonist, as a novel scaffold of the SET7/9 inhibitor. In this work, we focused on dibenzosuberene as a substructure of cyproheptadine and synthesized derivatives with various functional groups. Among them, the compound

  组蛋白甲基转移酶SET7 / 9不仅将组蛋白甲基化，而且使非组蛋白蛋白质作为底物，因此，SET7 / 9抑制剂被认为是治疗疾病的候选药物。以前，我们的研究小组确定在临床上用作血清素受体拮抗剂和组胺受体（H1）拮抗剂的赛庚啶是SET7 / 9抑制剂的新型支架。在这项工作中，我们重点研究了二苯并亚戊烯作为赛庚啶的一个子结构，并合成了具有各种官能团的衍生物。其中，带有2-羟基的化合物显示出最强的活性。另一方面，3-羟基或另一个亲水性官能团（如乙酰胺）会降低活性。结构分析阐明了仅通过严格限制亲水基团的位置和类型来提高效力的理由。另外，SET7 / 9环在与赛庚啶复合物中仅部分可见，而在与2-羟基赛庚啶复合物中更清晰可见。预期这些结果将有助于SET7 / 9抑制剂的进一步基于结构的开发。
• Cyclo-octane neuroprotective agents
  申请人：Merck Sharp & Dohme Limited

  公开号：US04927819A1

  公开（公告）日：1990-05-22

  The present invention provides a compound of formula I: ##STR1## or a salt thereof, wherein: the dotted lines represent optional double bonds; R.sup.1 represents hydrogen, hydroxy, alkenyl, alkyl, aminoalkyl or hydroxyalkyl; R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently represet hydrogen, hydroxy, fluoro, alkenyl, aryl, alkyl, or alkyl substituted with aryl, amino, hydroxy, carboxy or fluoro; and R.sup.7, R.sup.8, R.sup.9 and R.sup.10 independently represent hydrogen, hydrocarbon or a heterocyclic group provided that R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are not simultaneously hydrogen; or R.sup.7 and R.sup.8 and/or R.sup.9 and R.sup.10 may complete a saturated or unsaturated C.sub.4-9 hydrocarbon or heterocyclic ring; which compounds are useful as anticonvulsant agents and in the treatment and/or prevention of neurodegenerative disorders.

  本发明提供了公式I的化合物：##STR1##或其盐，其中：虚线表示可选的双键；R.sup.1表示氢，羟基，烯基，烷基，氨基烷基或羟基烷基；R.sup.2、R.sup.3、R.sup.4、R.sup.5和R.sup.6独立地表示氢、羟基、氟、烯基、芳基、烷基或烷基取代的芳基、氨基、羟基、羧基或氟；而R.sup.7、R.sup.8、R.sup.9和R.sup.10独立地表示氢、碳氢化合物或杂环基团，但要求R.sup.7、R.sup.8、R.sup.9和R.sup.10不能同时为氢；或R.sup.7和R.sup.8和/或R.sup.9和R.sup.10可以组成饱和或不饱和的C.sub.4-9碳氢化合物或杂环环；这些化合物可用作抗癫痫药物，以及用于治疗和/或预防神经退行性疾病。
• Dibenzocycloheptenylidenes
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0115690A1

  公开（公告）日：1984-08-15

  Compounds having the formula: wherein R4 is hydrogen or chloro; R5 is carboxy, an ester thereof, or tetrazolyl; R2 is hydrogen, halo, or alkoxy of 1 to 4 carbon atoms; and R3 is hydrogen or bromo, with the proviso that when R4 is hydrogen, R5 is carboxy and R2 or R3 is other than hydrogen; and that when R4, R2 and R3 are all hydrogen, R5 is tetrazolyl; the stereoisomers thereof and the pharmaceutically acceptable salts thereof. The compounds of formula B wherein R5 is carboxy or tetrazolyl have pharmaceutical utility eg. as anti-inflammatory agents. The compounds where R5 is a carboxylic ester are intermediates for the corresponding acids. Pharmaceutical composition containing the active compounds are also disclosed.

  具有以下式子的化合物 其中 R4 为氢或氯； R5 是羧基、其酯或四唑基 R2 是氢、卤素或 1 至 4 个碳原子的烷氧基；以及 R3 是氢或溴，但当 R4 是氢时，R5 是羧基，R2 或 R3 不是氢；当 R4、R2 和 R3 都是氢时，R5 是四唑基；其立体异构体及其药学上可接受的盐。其中 R5 为羧基或四唑基的式 B 化合物具有医药用途，例如可用作抗炎剂。R5 为羧酸酯的化合物是相应酸类的中间体。还公开了含有活性化合物的药物组合物。