5-(benzyloxy)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid | 405102-95-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(benzyloxy)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid
• 英文别名: 5-benzyloxy-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid；5-Benzyloxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid；5-phenylmethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid
• CAS: 405102-95-6
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: RIYPIHTZBKWIDL-UHFFFAOYSA-N

物化性质

• 沸点：
  485.2±45.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(benzyloxy)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid 在 palladium on activated charcoal 硫酸 、 氢气 、 potassium carbonate 、 sodium iodide 、 lithium chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 39.0h， 生成 5-{3-[(2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propoxy}-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid
  参考文献：
  名称：

  [EN] COMPOUNDS AND METHODS
  [FR] COMPOSES ET PROCEDES

  摘要：

  公开号：

  WO2005023188A3
• 作为产物：
  描述：

  在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 以57%的产率得到5-(benzyloxy)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid
  参考文献：
  名称：

  The discovery of tertiary-amine LXR agonists with potent cholesterol efflux activity in macrophages

  摘要：

  The liver X receptors (LXR) play a key role in cholesterol homeostasis and lipid metabolism. SAR studies around tertiary-amine lead molecule 2, an LXR full agonist, revealed that steric and conformational changes to the acetic acid and propanolamine groups produce dramatic effects on agonist efficacy and potency. The new analogs possess good functional activity, demonstrating the ability to upregulate LXR target genes, as well as promote cholesterol efflux in macrophages. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.036

文献信息

• Highly Diastereoselective Esterification of Ketenes Generated In Situ from Acyl Chlorides with (<i>R</i>)-Pantolactone Derivatives
  作者：Takafumi Yamagami、Masanori Hatsuda、Masayuki Utsugi、Ryo Kobayashi、Yasunori Moritani

  DOI：10.1002/ejoc.201301383

  日期：2013.11

  revealed that Et3N is a key requirement for the highly diastereoselective formation of esters from the corresponding acyl chlorides with (R)-pantolactone via ketene-derived complexes. Furthermore, we have discovered that (R)-N-benzyl-pantolactam is a more effective chiral alcohol than (R)-pantolactone for the esterification of in situ generated ketenes.

  我们的机理研究表明，Et3N 是通过乙烯酮衍生的复合物从相应的酰氯与 (R)-泛内酯形成高度非对映选择性形成酯的关键要求。此外，我们发现 (R)-N-苄基-泛内酰胺是比 (R)-泛内酯更有效的手性醇，用于原位生成的烯酮的酯化。
• Novel amide derivatives and medicinal use thereof ugs
  申请人：——

  公开号：US20040138223A1

  公开（公告）日：2004-07-15

  The present invention relates to an amide derivative of the formula (1), having a C5a receptor antagonistic action 1 wherein each symbol is as defined in the specification. The above-mentioned amide derivative, an optically active form thereof and a pharmaceutically acceptable salt thereof are promising as an agent for the treatment or prophylaxis of diseases or syndromes caused by inflammation caused by C5a [e.g., autoimmune diseases such as rheumatism, systemic lupus erythematosus and the like, sepsis, adult respiratory distress syndrome, chronic obstructive pulmonary disease, allergic diseases such as asthma and the like, atherosclerosis, cardiac infarction, brain infarction, psoriasis, Alzheimer's disease and serious organ injury (e.g., pneumonia, nephritis, hepatitis and pancreatitis and the like) due to activation of leukocytes caused by ischemia reperfusion, trauma, burn, surgical invasion and the like]. Moreover, they are useful as a therapeutic or prophylactic agent for the infectious diseases caused by bacteria and virus that invade via a C5a receptor.

  本发明涉及一种式（1）的酰胺衍生物，具有C5a受体拮抗作用，其中每个符号如规范中所定义。上述酰胺衍生物及其光学活性形式和药学上可接受的盐被认为是治疗或预防因C5a引起的炎症引起的疾病或综合症的药物，如自身免疫性疾病，如风湿病，系统性红斑狼疮等，败血症，成人呼吸窘迫综合症，慢性阻塞性肺疾病，哮喘等过敏性疾病，动脉粥样硬化，心脏梗死，脑梗死，牛皮癣，老年痴呆症和严重器官损伤（如肺炎，肾炎，肝炎，胰腺炎等）由于缺血再灌注，创伤，烧伤，手术入侵等引起的白细胞激活。此外，它们对通过C5a受体侵入的细菌和病毒引起的传染病也有用作治疗或预防剂。
• Optically Active Tetrahydronaphthalene Derivative
  申请人：Nakamura Mitsuharu

  公开号：US20080194640A1

  公开（公告）日：2008-08-14

  A compound represented by the following formula (I), a pharmacologically acceptable salt thereof or a hydrate thereof or a solvate thereof, which shows not only a C5a receptor antagonistic activity but also high activity in the biological availability, as compared to its racemate.

  以下式子(I)所代表的化合物，其药理学上可接受的盐、水合物或溶剂化物，不仅显示出C5a受体拮抗活性，而且相对于其外消旋体具有高生物利用度的活性。
• Novel amide derivatives and medicinal use thereof
  申请人：NAKAMURA Mitsubaru

  公开号：US20100041656A1

  公开（公告）日：2010-02-18

  The present invention relates to an amide derivative of the formula (1), having a C5a receptor antagonistic action wherein each symbol is as defined in the specification. The above-mentioned amide derivative, an optically active form thereof and a pharmaceutically acceptable salt thereof are promising as an agent for the treatment or prophylaxis of diseases or syndromes caused by inflammation caused by C5a [e.g., autoimmune diseases such as rheumatism, systemic lupus erythematosus and the like, sepsis, adult respiratory distress syndrome, chronic obstructive pulmonary disease, allergic diseases such as asthma and the like, atherosclerosis, cardiac infarction, brain infarction, psoriasis, Alzheimer's disease and serious organ injury (e.g., pneumonia, nephritis, hepatitis and pancreatitis and the like) due to activation of leukocytes caused by ischemia reperfusion, trauma, burn, surgical invasion and the like]. Moreover, they are useful as a therapeutic or prophylactic agent for the infectious diseases caused by bacteria and virus that invade via a C5a receptor.

  本发明涉及一种式（1）的酰胺衍生物，具有C5a受体拮抗作用，其中每个符号如规范中所定义。上述酰胺衍生物及其光学活性形式和药学上可接受的盐被认为是治疗或预防由C5a引起的炎症所致疾病或综合症的药物，例如自身免疫性疾病，如风湿病，系统性红斑狼疮等，败血症，成人呼吸窘迫综合症，慢性阻塞性肺疾病，过敏性疾病，如哮喘等，动脉硬化，心脏梗塞，脑梗塞，牛皮癣，阿尔茨海默病和严重器官损伤（例如，肺炎，肾炎，肝炎，胰腺炎等），由缺血再灌注，创伤，烧伤，手术侵袭等引起的白细胞激活所致。此外，它们还可用作通过C5a受体侵入的细菌和病毒引起的传染病的治疗或预防剂。
• Amide derivatives and medicinal use thereof
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：US07855297B2

  公开（公告）日：2010-12-21

  The present invention relates to an amide derivative of the formula (1), having a C5a receptor antagonistic action wherein each symbol is as defined in the specification. The above-mentioned amide derivative, an optically active form thereof and a pharmaceutically acceptable salt thereof are promising as an agent for the treatment or prophylaxis of diseases or syndromes caused by inflammation caused by C5a [e.g., autoimmune diseases such as rheumatism, systemic lupus erythematosus and the like, sepsis, adult respiratory distress syndrome, chronic obstructive pulmonary disease, allergic diseases such as asthma and the like, atherosclerosis, cardiac infarction, brain infarction, psoriasis, Alzheimer's disease and serious organ injury (e.g., pneumonia, nephritis, hepatitis and pancreatitis and the like) due to activation of leukocytes caused by ischemia reperfusion, trauma, burn, surgical invasion and the like]. Moreover, they are useful as a therapeutic or prophylactic agent for the infectious diseases caused by bacteria and virus that invade via a C5a receptor.

  本发明涉及一种具有C5a受体拮抗作用的公式（1）的酰胺衍生物，其中每个符号如规范中所定义。上述酰胺衍生物及其光学活性形式和药学上可接受的盐作为治疗或预防由C5a引起的炎症引起的疾病或综合征的药物很有前途[例如，自身免疫疾病，如风湿病，系统性红斑狼疮等，败血症，成人呼吸窘迫综合症，慢性阻塞性肺疾病，过敏疾病，如哮喘等，动脉硬化，心肌梗死，脑梗死，牛皮癣，阿尔茨海默病和严重器官损伤（例如，由缺血再灌注，创伤，烧伤，手术入侵等引起的白细胞激活引起的肺炎，肾炎，肝炎和胰腺炎等）]。此外，它们也可用作通过C5a受体侵入的细菌和病毒引起的传染病的治疗或预防药物。