2-Hydroxydibenzocyclohepten-5-one | 17910-79-1

• 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-Hydroxydibenzocyclohepten-5-one
• 英文别名: 2-hydroxy-5H-dibenzo[a,d][7]annulen-5-one；6-Hydroxytricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-2-one
• CAS: 17910-79-1
• 化学式: C₁₅H₁₀O₂
• 分子量: 222.243
• InChiKey: VTUJQLJFQZMEPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Hydroxydibenzocyclohepten-5-one 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.08h， 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) 、 三氯化铝 、 TEA 、 氢气 、 sodium acetate 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 为溶剂， 50.0~245.0 ℃ 、392.24 kPa 条件下， 反应 92.83h， 生成 2-Hydroxydibenzocyclohepten-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。
• Dibenzosuberyl and dibenzosuberenyl derivatives and their use as linker groups
  申请人：SHIMADZU CORPORATION

  公开号：EP0597400A1

  公开（公告）日：1994-05-18

  The present invention is directed to a compound represented by the following formula (I), and a linker for peptide synthesis using the above compound. When the linker of the present invention is used for the solid-phase peptide synthesis, it is possible to synthesize those peptides which are sensitive to acid and difficult to synthesize by conventional methods. Also, side reactions can be prevented, and the desired product is produced at a high purity because cleavage can be achieved under milder conditions or in shorter times. In other words, efficient peptide synthesis is possible.

  本发明涉及下式 (I) 所代表的化合物、 以及使用上述化合物进行多肽合成的连接剂。当本发明的连接剂用于固相肽合成时，可以合成那些对酸敏感和难以用传统方法合成的肽。此外，由于可以在较温和的条件下或在较短的时间内实现裂解，因此可以防止副反应，并生产出高纯度的所需产品。换句话说，高效的多肽合成成为可能。
• US4349561A
  申请人：——

  公开号：US4349561A

  公开（公告）日：1982-09-14
• US4448786A
  申请人：——

  公开号：US4448786A

  公开（公告）日：1984-05-15
• US5442122A
  申请人：——

  公开号：US5442122A

  公开（公告）日：1995-08-15