2-(苄氧基)-6,7,8,9-四氢苯并[7]轮烯-5-酮 | 35872-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(苄氧基)-6,7,8,9-四氢苯并[7]轮烯-5-酮
• 英文名称: 2-(benzyloxy)-6,7,8,9-tetrahydrobenzo[7]annulen-5-one
• 英文别名: 2-Benzyloxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one；2-benzyloxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one；2-Phenylmethoxy-6,7,8,9-tetrahydrobenzo[7]annulen-5-one
• CAS: 35872-54-9
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: VLFFRHATBZUYRK-UHFFFAOYSA-N

物化性质

• 沸点：
  445.9±34.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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-(苄氧基)-6,7,8,9-四氢苯并[7]轮烯-5-酮 在 palladium 10% on activated carbon 、 氢气 、 sodium hydride 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 C₁₅H₂₀O₃
  参考文献：
  名称：

  Identification of Fused-Ring Alkanoic Acids with Improved Pharmacokinetic Profiles that Act as G Protein-Coupled Receptor 40/Free Fatty Acid Receptor 1 Agonists

  摘要：

  The G protein-coupled receptor 40 (GPR40)/free fatty acid receptor 1 (FFA1) has emerged as an attractive target for a novel insulin secretagogue with glucose dependency. We previously identified phenylpropanoic acid derivative 1 (3-{4-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-2-fluorophenyl}propanoic acid) as a potent and orally available GPR40/FFA1 agonist; however, 1 exhibited high clearance and low oral bioavailability, which was likely due to its susceptibility to beta-oxidation at the phenylpropanoic acid moiety. To identify long-acting compounds, we attempted to block the metabolically labile sites at the phenylpropanoic acid moiety by introducing a fused-ring structure. Various fused-ring alkanoic acids with potent GPR40/FFA1 activities and good PK profiles were produced. Further optimizations of the lipophilic portion and the acidic moiety led to the discovery of dihydrobenzofuran derivative 53 ((6-{[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methoxy}-2,3-dihydro-1-benzofuran-3-yl)acetic acid), which acted as a GPR40/FFA1 agonist with in vivo efficacy during an oral glucose tolerance test (OGTT) in rats with impaired glucose tolerance.

  DOI：

  10.1021/jm2012968
• 作为产物：
  描述：

  (3-丙羧基)三苯基溴化膦 在 aluminum (III) chloride 、 甲烷磺酸 、 四磷十氧化物 、 platinum on activated charcoal 、 氢气 、 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 甲醇 、 乙腈 、 苯 为溶剂， 生成 2-(苄氧基)-6,7,8,9-四氢苯并[7]轮烯-5-酮
  参考文献：
  名称：

  Photo-Favorskii 环收缩反应：环尺寸的影响

  摘要：

  环大小对光法沃斯基诱导的羟基苯并环烷酰乙酸酯和甲磺酸酯（7a - d，8a - c）环收缩反应的影响为重排机制提供了新的见解。通过单调减小这些环状衍生物中的环尺寸，对难以捉摸的双环螺环丙酮20的形成施加的环应变的增加导致远离重排和溶剂解的分歧。七或八个碳的环烷酮经历高效的光法沃斯基重排，环收缩与对羟基苯甲酰酯的光化学平行。相比之下，五碳环不会重排，而是转移到光解通道，避免了螺二环酮（“Favorskii 中间体20 ” ）形成过程中应变能的增加。六碳类似物证明了反应通道的分叉，产生了两者的溶剂敏感混合物。通过将时间分辨吸收测量、量子产率测定、同位素标记和溶剂变化研究与理论处理相结合，对重排的更全面的机制描述已经出现。

  DOI：

  10.1021/jo300850a

文献信息

• BENZOCYCLOHEPTENES, PROCESS FOR THEIR PRODUCTION, PHARMACEUTICAL PREPARATIONS THAT CONTAIN THE LATTER AS WELL AS THEIR USE FOR THE PRODUCTION OF PHARMACEUTICAL AGENTS
  申请人：——

  公开号：US20020068765A1

  公开（公告）日：2002-06-06

  This invention describes the new benzocycloheptenes of general formula I 1 in which R 1 , R 2 and SK have the meanings that are indicated in the description. The new compounds have selective estrogenic activity on bones and are suitable for the production of pharmaceutical agents, especially for prophylaxis and therapy of osteoporosis.

  这项发明描述了一种新的苯并环庚烯，其通用式为I1，其中R1、R2和SK的含义如描述中所示。这些新化合物对骨骼具有选择性雌激素活性，适用于生产药物制剂，特别是用于骨质疏松症的预防和治疗。
• Condensed ring compound
  申请人：Yasuma Tsuneo

  公开号：US20060258722A1

  公开（公告）日：2006-11-16

  The present invention aims at providing a novel fused ring compound having a GPR40 receptor function modulating action and being useful as an insulin secretagogue or a pharmaceutical agent for the prophylaxis or treatment of diabetes, more particularly, a compound represented by the formula: wherein Ar is an optionally substituted cyclic group, ring A is a ring optionally further substituted (provided that the ring is not thiazole, oxazole, imidazole and pyrazole), Xa and Xb are each independently a bond or a spacer having a main chain of 1 to 5 atom(s), Xc is O, S, SO or SO 2 , ring B is a 5- to 7-membered ring, Xd is a bond, CH or CH 2 , is a single bond when Xd is a bond or CH 2 , or a double bond when Xd is CH, and R 1 is an optionally substituted hydroxy group, and a salt thereof.

  本发明旨在提供一种新的融合环化合物，具有GPR40受体功能调节作用，并可用作胰岛素分泌剂或用于预防或治疗糖尿病的药物，更具体地说，是一种由以下公式表示的化合物：其中Ar是一个可选取代的环状基团，环A是一个环状基团，可选地进一步取代（前提是该环不是噻唑、噁唑、咪唑和吡唑），Xa和Xb分别是1到5个原子的主链具有键或间隔物，Xc是O、S、SO或SO2，环B是一个5-至7-成员环，Xd是键、CH或CH2，当Xd是键或CH2时为单键，当Xd为CH时为双键，R1为可选取代的羟基，以及其盐。
• CONDENSED RING COMPOUND
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1630152A1

  公开（公告）日：2006-03-01

  The present invention aims at providing a novel fused ring compound having a GPR40 receptor function modulating action and being useful as an insulin secretagogue or a pharmaceutical agent for the prophylaxis or treatment of diabetes, more particularly, a compound represented by the formula: wherein Ar is an optionally substituted cyclic group, ring A is a ring optionally further substituted (provided that the ring is not thiazole, oxazole, imidazole and pyrazole), Xa and Xb are each independently a bond or a spacer having a main chain of 1 to 5 atom(s), Xc is O, S, SO or SO2, is ring B is a 5- to 7-membered ring, Xd is a bond, CH or CH2, •••••• is a single bond when Xd is a bond or CH2, or a double bond when Xd is CH, and R1 is an optionally substituted hydroxy group, and a salt thereof.

  本发明旨在提供一种新型融合环化合物，该化合物具有调节 GPR40 受体功能的作用，可用作预防或治疗糖尿病的胰岛素分泌剂或药物制剂，特别是由式表示的化合物： 其中 Ar 是任选取代的环状基团，环 A 是任选进一步取代的环（条件是该环不是噻唑、噁唑、咪唑和吡唑），Xa 和 Xb 各自独立地是键或主链为 1 至 5 个原子的间隔物，Xc 是 O、S、SO 或 SO2、 是 环 B 是 5 至 7 元环、 Xd 是键、CH 或 CH2、 ------ 是单键（当 Xd 是键或 CH2 时）或双键（当 Xd 是 CH 时），以及 R1 是任选取代的羟基及其盐。
• Benzocycloheptenes, process for their production, pharmaceutical preparations that contain the latter as well as their use for the production of pharmaceutical agents
  申请人：Schering AG

  公开号：US20030050324A1

  公开（公告）日：2003-03-13

  This invention describes the new benzocycloheptenes of general formula I 1 in which R 1 , R 2 and SK have the meanings that are indicated in the description. The new compounds have selective estrogenic activity on bones and are suitable for the production of pharmaceutical agents, especially for prophylaxis and therapy of osteoporosis.

  本发明描述了通式 I 的新型苯并环庚烯化合物 1 其中 R 1 , R 2 和 SK 的含义如说明所示。新化合物对骨骼具有选择性雌激素活性，适用于生产药剂，特别是用于预防和治疗骨质疏松症。
• 苯并七元环类双功能化合物及其应用
  申请人：南京明德新药研发有限公司

  公开号：CN117466870A

  公开（公告）日：2024-01-30

  本发明涉及一类苯并七元环类双功能化合物及其应用，具体涉及式(IV)所示化合物及其药学上可接受的盐。#imgabs0#