5,6,8,9-四氢-苯并环庚烯-7-酮 | 37949-03-4

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 苯类化合物
• 中文名称: 5,6,8,9-四氢-苯并环庚烯-7-酮
• 中文别名: 8,9-二氢-5H-苯并[7]轮烯-7(6H)-酮
• 英文名称: 5,6,8,9-tetrahydrobenzo[7]annulen-7-one
• 英文别名: 7-benzocycloheptanone；6,7,8,9-tetrahydro-5H-benzocyclohepten-7-one；8,9-Dihydro-5H-benzo[7]annulen-7(6H)-one
• CAS: 37949-03-4
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: MRLBDJHIJZHYMK-UHFFFAOYSA-N

物化性质

• 熔点：
  38.5 °C
• 沸点：
  288.2±29.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319
• 储存条件：
  存放在室温下，应保持干燥和密封。

反应信息

• 作为反应物：
  描述：

  5,6,8,9-四氢-苯并环庚烯-7-酮 在 硫酸 、 palladium on activated charcoal 、 氢气 、 硝酸 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 甲醇 、 硝基甲烷 、 1,2-二氯乙烷 、 异丙醇 为溶剂， 生成 1-(6,7-二氢-5H-苯并[6,7]环庚烷并[1,2-c]哒嗪-3-基)-N3-[(7S)-6,7,8,9-四氢-7-(1-吡咯烷基)-5H-苯并环庚烯-2-基]-1H-1,2,4-三唑-3,5-二胺
  参考文献：
  名称：

  Bemcentinib. Tyrosine-protein kinase receptor UFO (Axl) inhibitor, Treatment of cancer

  摘要：

  Increased expression of Axl has been reported in various cancers including colon, esophageal, thyroid, breast, lung, liver and astrocytoma-glioblastoma. Cancer resistance to tyrosine kinase inhibitors and other chemotherapeutics has been correlated with aberrant expression of Axl. These findings support the development of Axl inhibitors in combination with targeted agents to tackle acquired resistance and high Axl levels. Bemcentinib (BGB-324, R-428) is an oral, potent and selective small-molecule inhibitor of Axl kinase in vitro with IC50 values in the low nanomolar range. In preclinical studies, bemcentinib demonstrated efficacy across multiple cancer models. It has also shown a favorable safety profile in clinical studies in cancer patients, and encouraging activity in acute myeloid leukemia (AML) and non-small cell lung cancer (NSCLC). Currently, there are phase II studies with bemcentinib ongoing in advanced NSCLC, triple-negative breast cancer, AML and myelodysplastic syndromes, and metastatic melanoma. Orphan drug designation was granted by the U.S. Food and Drug Administration for the treatment of AML.

  DOI：

  10.1358/dof.2018.043.09.2808543
• 作为产物：
  描述：

  1,2-双(2-溴乙基)苯 在 乙醚 、 硫酸 、 苯基锂 、 N-甲基苯胺 作用下， 生成 5,6,8,9-四氢-苯并环庚烯-7-酮
  参考文献：
  名称：

  Azabenzazulenes. I. 1-Azadibenz[b,f]azulene

  摘要：

  DOI：

  10.1021/ja01609a061

文献信息

• Carboxamides useful as inhinitors of microsomal triglyceride transfer protein and of apolipoprotein b secretion
  申请人：——

  公开号：US20030109700A1

  公开（公告）日：2003-06-12

  1 Compounds of formula (1) wherein R 2 —C, R 3 —C, R 4 —C or R 5 —C may be replaced by N; and wherein n is 1, 2 or 3; R 1 is aryl, heteroaryl or (aryl or heteroaryl)-lower alkoxy; R 2 , R 3 , R 4 and R 5 are independently hydrogen, lower alkyl, lower alkoxy, halo, trifluoromethyl or cyano; R 6 is (i) or (ii) m is 1, 2 or 3; R 7 is hydrogen, lower alkyl (aryl or heteroaryl)-lower alkyl, lower alkoxy, (aryl or heteroaryl)-lower alkoxy, hydroxy, oxo, lower alkylenedioxy or lower alkanoyloxy; W is O, S or NR 8 ; R 8 is —COR a , (iii), —COOR d , —SO 2 R e , hydrogen, optionally substituted lower alkyl, aryl, heteroaryl or (aryl or heteroaryl)-lower alkyl; R a , R d and R e , are independently optionally substituted lower alkyl, cycloalkyl, adamantyl, aryl, heteroaryl or (aryl or heteroaryl)-lower alkyl; R b and R c are independently hydrogen, cycloalkyl, optionally substituted lower alkyl, aryl, heteroaryl or (aryl or heteroaryl) lower alkyl; or R b and R c together represent lower alkylene; and pharmaceutically acceptable salts thereof; and enantiomers thereof; which are useful as inhibitors of microsomal triglyceride transfer protein (MTP) and of apolipoprotein B (apoB) secretion.

  式（1）的化合物中，其中R2—C，R3—C，R4—C或R5—C可以被N取代；其中n为1、2或3；R1为芳基，杂环芳基或（芳基或杂环芳基）-较低烷氧基；R2、R3、R4和R5独立地为氢、较低烷基、较低烷氧基、卤素、三氟甲基或氰基；R6为（i）或（ii）m为1、2或3；R7为氢、较低烷基（芳基或杂环芳基）-较低烷基、较低烷氧基、（芳基或杂环芳基）-较低烷氧基、羟基、氧代、较低烷二氧基或较低烷酰氧基；W为O、S或NR8；R8为—CORa、（iii）、—COORd、—SO2Re、氢、可选择取代的较低烷基、芳基、杂环芳基或（芳基或杂环芳基）-较低烷基；Ra、Rd和Re独立地为可选择取代的较低烷基、环烷基、脱氢脂肪基、芳基、杂环芳基或（芳基或杂环芳基）-较低烷基；Rb和Rc独立地为氢、环烷基、可选择取代的较低烷基、芳基、杂环芳基或（芳基或杂环芳基）较低烷基；或Rb和Rc一起代表较低烷基；以及其药学上可接受的盐；以及其对映体；它们可用作微粒体三酰甘油转移蛋白（MTP）和载脂蛋白B（apoB）分泌的抑制剂。
• Two-Carbon Ring Expansion of 1-Indanones via Insertion of Ethylene into Carbon–Carbon Bonds
  作者：Ying Xia、Shusuke Ochi、Guangbin Dong

  DOI：10.1021/jacs.9b07445

  日期：2019.8.21

  A rhodium-catalyzed direct insertion of ethylene into a relatively unstrained carbon-carbon bond in 1-indanones is reported, which provides a two-carbon ring-expansion strategy for preparing seven-membered cyclic ketones. As many 1-indanones are commercially available and ethylene is inexpensive, this strategy simplifies synthesis of benzocycloheptenones that are valuable synthetic intermediates for

  据报道，铑催化乙烯直接插入 1-茚满酮中相对无应变的碳-碳键，为制备七元环酮提供了一种双碳扩环策略。由于许多 1-茚满酮可商购获得且乙烯价格低廉，因此该策略简化了苯并环庚烯酮的合成，苯环庚烯酮是生物活性化合物的宝贵合成中间体，但在其他方面制备具有挑战性。此外，该反应无副产物，氧化还原中性，并且可以耐受多种官能团，这可能对制备复杂环状分子的非常规战略键断开产生影响。
• Unexpected Metal-Free Transformation of<i>gem</i>-Dibromomethylenes to Ketones under Acetylation Conditions
  作者：Rino Kimura、Yusuke Sawayama、Atsuo Nakazaki、Kazunori Miyamoto、Masanobu Uchiyama、Toshio Nishikawa

  DOI：10.1002/asia.201403277

  日期：2015.4

  Novel conditions for the transformation of gem‐dibromomethylenes to ketones are described. gem‐Dibromo compounds were treated with acetic anhydride and triethylamine in dichloromethane/water at room temperature under an air atmosphere to give the corresponding ketones in moderate yields. A radical mechanism is proposed based on experimental results.

  描述了将二溴代亚甲基宝石转变为酮的新条件。室温下，在空气中于二氯甲烷/水中，用乙酸酐和三乙胺处理gem- Dibromo化合物，以适当的收率得到相应的酮。根据实验结果提出了一种根本机理。
• HMG-CoA reductase inhibitors
  申请人：Stein Philip D.

  公开号：US20070249583A1

  公开（公告）日：2007-10-25

  Compounds are provided of the following structure are HMG CoA reductase inhibitors and thus are active in inhibiting cholesterol biosynthesis, modulating blood serum lipids, for example, lowering LDL cholesterol and/or increasing HDL cholesterol, and treating hyperlipidemia and dyslipidemia, hypercholesterolemia, hypertriglyceridemia and atherosclerosis wherein A is chosen from B is chosen from wherein the variables R 1 to R 7 , m, n, are as defined herein. A method for treating the above diseases employing the above compounds is also provided.

  提供以下结构的化合物是HMG CoA还原酶抑制剂，因此在抑制胆固醇生物合成、调节血清脂质，例如降低LDL胆固醇和/或增加HDL胆固醇，以及治疗高脂蛋白血症和血脂异常、高胆固醇血症、高甘油三酯血症和动脉粥样硬化方面具有活性。 其中A选择自 B选择自 其中变量R1至R7，m，n， 如本文所定义。 还提供了一种利用上述化合物治疗上述疾病的方法。
• Amino-benzocycloalkane derivatives
  申请人：Novartis AG

  公开号：US06197798B1

  公开（公告）日：2001-03-06

  Compounds of the formula I wherein R2—C, R3—C, R4—C or R5—C may be replaced by N; and wherein n is 1, 2 or 3; R1 is aryl, cycloalkyl or heterocyclyl; R2, R3, R4 and R5 are independently hydrogen, optionally substituted alkyl, halo, amino, substituted amino, trifluoromethyl, cyano, carboxyl, alkoxycarbonyl, aralkoxycarbonyl, (alkyl, aryl or aralkyl)-thio, (alkyl, aryl or aralkyl)-oxy, acyloxy, (alkyl, aryl or aralkyl)-aminocarbonyloxy; or any two of R2, R3, R4 and R5 at adjacent positions are alkylenedioxy; R6 is hydrogen, optionally substituted alkyl, amino, substituted amino, acylamino, wherein Ra is hydrogen or optionally substituted alkyl, Rb and Rc are independently hydrogen, optionally substituted alkyl, cycloalkyl, aryl or heterocyclyl; or Rb and Rc together represent lower alkylene or lower alkylene interrupted by O, S, or N—(H, alkyl or aralkyl); Rd is optionally substituted alkyl, cycloalkyl, aryl or heterocyclyl; and Re is optionally substituted alkyl, aryl, heterocyclyl, cycloalkyl, amino or substituted amino; and pharmaceutically acceptable salts thereof; and enantiomers thereof; which are useful as inhibitors of microsomal triglyceride transfer protein (MTP) and of apolipoprotein B (ApoB) secretion.

  根据您的要求，以下是公式I化合物的中文翻译： 化合物具有公式I，其中R2—C、R3—C、R4—C或R5—C可以被N取代；并且其中n为1、2或3；R1为芳基、环烷基或杂环基；R2、R3、R4和R5独立地为氢、可选地取代的烷基、卤素、氨基、取代氨基、三氟甲基、氰基、羧基、烷氧羰基、芳烷氧羰基、(烷基、芳基或芳烷基)硫基、(烷基、芳基或芳烷基)氧基、酰氧基、(烷基、芳基或芳烷基)氨基甲氧基；或者R2、R3、R4和R5中任意两个相邻位置的为烷基亚甲基二氧基；R6为氢、可选地取代的烷基、氨基、取代氨基、酰氨基，其中Ra为氢或可选地取代的烷基，Rb和Rc独立地为氢、可选地取代的烷基、环烷基、芳基或杂环基；或者Rb和Rc共同代表低碳烯基或由O、S或N—(H、烷基或芳烷基)打断的低碳烯基；Rd为可选地取代的烷基、环烷基、芳基或杂环基；Re为可选地取代的烷基、芳基、杂环基、环烷基、氨基或取代氨基；以及药用可接受的盐；以及它们的对映体；这些化合物可用作微粒体甘油三酯转移蛋白（MTP）和载脂蛋白B（ApoB）分泌的抑制剂。