2,3-二氢-4-甲氧基-1-茚羧酸 | 125067-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 中文名称: 2,3-二氢-4-甲氧基-1-茚羧酸
• 英文名称: 2,3-Dihydro-4-methoxy-1-indene carboxylic acid
• 英文别名: 4-methoxyindan-1-carboxylic acid；4-Methoxy-2,3-dihydro-1H-indene-1-carboxylic acid
• CAS: 125067-71-2
• 化学式: C₁₁H₁₂O₃
• mdl: MFCD11219722
• 分子量: 192.214
• InChiKey: CMRDEBQEQQRVER-UHFFFAOYSA-N

物化性质

• 沸点：
  368.5±42.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  2,3-二氢-4-甲氧基-1-茚羧酸 在 苯基氯化硒 、 sodium hexamethyldisilazane 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 7-methoxyindene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of methoxy and hydroxy analogs of 1,2,3,4,4a,9a-hexahydro-4a-fluorenamine: rigid phencyclidine analogs as probes of phencyclidine binding site topography

  摘要：

  (+)-1,2,3,4,4a,9a-六氢-4a-荧蒽胺（HFA）发现是对N-甲基-D-天冬氨酸（NMDA）受体的苯环己哌啶（PCP）结合位点具有强大且选择性的配体。这一构象刚性的PCP类似物提供了关于PCP结合构象及其结合位点地形的信息。为了进一步探索PCP结合位点的地形，开发了合成六种氧代HFA类似物的方法，这些类似物作为推测的配体与该结合位点之间氢键相互作用的探针。这一部分化学涉及了适当取代的甲基茚-3-羧酸酯与丁二烯的Diels-Alder反应。因此，设计了所有可能的单甲氧基化茚-3-羧酸酯的合成路线，并在本文中详细说明。还开发了一种替代方法来生成1-茚酮的同烯醇盐等价物，并证明叔丁基酯在Friedel-Crafts酰化反应中可作为阻胺酸等价物。

  DOI：

  10.1021/jo00014a033
• 作为产物：
  描述：

  氢化肉桂酸内酯 在 盐酸 、 sodium hydroxide 、 正丁基锂 、 三氯化铝 、 对甲苯磺酸 、 溶剂黄146 、 sodium chloride 作用下， 以 苯 为溶剂， 反应 38.0h， 生成 2,3-二氢-4-甲氧基-1-茚羧酸
  参考文献：
  名称：

  Synthesis of methoxy and hydroxy analogs of 1,2,3,4,4a,9a-hexahydro-4a-fluorenamine: rigid phencyclidine analogs as probes of phencyclidine binding site topography

  摘要：

  (+)-1,2,3,4,4a,9a-六氢-4a-荧蒽胺（HFA）发现是对N-甲基-D-天冬氨酸（NMDA）受体的苯环己哌啶（PCP）结合位点具有强大且选择性的配体。这一构象刚性的PCP类似物提供了关于PCP结合构象及其结合位点地形的信息。为了进一步探索PCP结合位点的地形，开发了合成六种氧代HFA类似物的方法，这些类似物作为推测的配体与该结合位点之间氢键相互作用的探针。这一部分化学涉及了适当取代的甲基茚-3-羧酸酯与丁二烯的Diels-Alder反应。因此，设计了所有可能的单甲氧基化茚-3-羧酸酯的合成路线，并在本文中详细说明。还开发了一种替代方法来生成1-茚酮的同烯醇盐等价物，并证明叔丁基酯在Friedel-Crafts酰化反应中可作为阻胺酸等价物。

  DOI：

  10.1021/jo00014a033

文献信息

• 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。
• 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。
• NOVEL AMIDE DERIVATIVES AND MEDICINAL USE THEREOF UGS
  申请人：Mitsubishi Pharma Corporation

  公开号：EP1318140A1

  公开（公告）日：2003-06-11

  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 受体拮抗作用的式 (1) 酰胺衍生物 其中各符号如说明书中所定义。 上述酰胺衍生物、其光学活性形式及其药学上可接受的盐有望用作治疗或预防由 C5a 引起的炎症所导致的疾病或综合征[例如、自身免疫性疾病，如风湿病、系统性红斑狼疮等；败血症；成人呼吸窘迫综合征；慢性阻塞性肺病；过敏性疾病，如哮喘等；动脉粥样硬化；心肌梗塞；脑梗塞；银屑病；老年痴呆症；严重器官损伤（如：肺炎、肾炎、肝硬化等）、由于缺血再灌注、创伤、烧伤、手术侵袭等引起的白细胞活化而导致的严重器官损伤（如肺炎、肾炎、肝炎和胰腺炎等）]。此外，它们还是治疗或预防细菌和病毒通过 C5a 受体入侵引起的感染性疾病的有效药物。
• NOVEL AMIDE DERIVATIVES AND MEDICINAL USE THEREOF
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP1318140B9

  公开（公告）日：2012-06-20