1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid ethyl ester | 41339-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid ethyl ester
• 英文别名: (1-methyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid ethyl ester；ethyl 2-(1-methyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl)acetate
• CAS: 41339-46-2
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: CCQGLFFEFDEDJR-UHFFFAOYSA-N

物化性质

• 沸点：
  421.9±35.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid
  参考文献：
  名称：

  Enzymatic Resolution of New Anti-inflammatory Drug Etodolac

  摘要：

  DOI：

  10.3987/com-97-s53
• 作为产物：
  描述：

  色醇 、 乙酰乙酸乙酯 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid ethyl ester
  参考文献：
  名称：

  Pyrano- and thiopyranoindole derivatives, compositions and methods of use

  摘要：

  本发明揭示了以氨基(较低)烷基基团连接到吡喃并[3,4-b]吲哚或硫代吡喃并[3,4-b]吲哚核的1和9位置中的一个或两个位置，或者连接到吡喃并[4,3-b]吲哚或硫代吡喃并[4,3-b]吲哚核的1位置的吡喃并吲哚或硫代吡喃并吲哚衍生物。氨基(较低)烷基基团的氨基部分可能进一步被一个或两个较低烷基基团取代，或者被并入一个杂环胺基团中。在位置1处仅具有氨基(较低)烷基基团的衍生物在位置1处进一步取代，并且可以选择地在位置3,4,5,6,7,8和9处取代。在位置9处仅具有氨基(较低)烷基基团的吡喃并[3,4-b]吲哚或硫代吡喃并[3,4-b]吲哚衍生物在位置1处具有两个取代基，并且可以选择地在位置3,4,5,6,7和8处取代；在位置1和9处均具有氨基(较低)烷基基团的衍生物在位置1处进一步取代，并且可以选择地在位置3,4,5,6,7和8处取代。本发明的吡喃并吲哚和硫代吡喃并吲哚衍生物是有用的抗抑郁和抗溃疡剂。还公开了这些衍生物的制备和使用方法。

  公开号：

  US04003913A1

文献信息

• 1,3,4,9-Tetrahydropyrano[3,4-b]indole-1-acetamides and derivatives
  申请人：American Home Products Corporation

  公开号：US03974179A1

  公开（公告）日：1976-08-10

  Indole derivatives characterized by having a 1,3,4,9-tetrahydropyrano[3,4-b]indole or 1,3,4,9-tetrahydrothiopyrano[3,4-b]indole nucleus bearing a substituent in position 1, said substituent incorporating an acid, ester or amide function therein, are disclosed. The nucleus is further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7, 8, and 9. The derivatives are useful antiinflammatory, analgesic, antibacterial and antifungal agents and methods for their preparation and use are also disclosed.

  具有1,3,4,9-四氢吡喃并[3,4-b]吲哚或1,3,4,9-四氢硫代吡喃并[3,4-b]吲哚核心，在位置1带有取代基的吲哚衍生物揭示了。所述取代基在其中包含酸、酯或酰胺功能。该核心在位置1进一步取代，可以选择性地在位置3、4、5、6、7、8和9处取代。这些衍生物是有用的抗炎、镇痛、抗菌和抗真菌剂，还公开了它们的制备和使用方法。
• New enzymatic and chemical approaches to enantiopure etodolac
  作者：Elisabetta Brenna、Claudio Fuganti、Daniela Fuganti、Piero Grasselli、Luciana Malpezzi、Giuseppe Pedrocchi-Fantoni

  DOI：10.1016/s0040-4020(97)10242-3

  日期：1997.12

  (+)- and (-)-etodolac enantiomers were prepared both by classical resolution via crystallisation of diastereoisomeric salts with (+) and (-)-alpha-methylbenzylamine, and by suitable manipulation of derivatives (-)-3- and (+)-4, obtained by lipase-catalysed kinetic resolution of racemic 3. X-ray diffraction analysis of the 4-bromobenzoate derivative of (+)-3, obtained from enantiopure acetate (+)-4, allowed us to determine the absolute (R) configuration of(-)-etodolac. (C) 1997 Elsevier Science Ltd.

  (+)和(-)异构体的托美汀是通过经典的解析方法制备的，具体是通过与(+)和(-)-α-甲基苄胺形成对映异构盐并在结晶过程中解析对映体，同时也是通过对由脂肪酶催化的对映纯托美汀3的对映异构体的修饰。通过对从对映纯醋酸盐(+)4获得的(+)3的4-溴苯甲酸衍生物进行X射线衍射分析，我们确定了(-)-托美汀的绝对(R)构型。© 1997 Elsevier Science Ltd.
• Certain pyrano [3,4-b]indoles and thiopyrano[3,4-b]indoles
  申请人：American Home Products Corporation

  公开号：US03939178A1

  公开（公告）日：1976-02-17

  Indole derivatives characterized by having a 1,3,4,9-tetrahydropyrano[3,4-b]indole or 1,3,4,9-tetrahydrothiopyrano[3,4-b]indole nucleus bearing a substituent in position 1, said substituent incorporating an acid, ester or amide function therein, are disclosed. The nucleus is further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7, 8, and 9. The derivatives are useful antiinflammatory, analgesic, antibacterial and antifungal agents and methods for their preparation and use are also disclosed.

  本发明揭示了一种具有1,3,4,9-四氢吡喃并[3,4-b]吲哚或1,3,4,9-四氢硫吡喃并[3,4-b]吲哚核的吲哚衍生物，其在1位带有酸、酯或酰胺功能的取代基。该核在1位进一步取代，且可以选择在3、4、5、6、7、8和9位上进行取代。这些衍生物是有用的抗炎、镇痛、抗菌和抗真菌剂，并且揭示了其制备和使用方法。
• Process for preparing pyrano[3,4-b]indole or thio pyrano[3,4-b]indole
  申请人：American Home Products Corporation

  公开号：US04012417A1

  公开（公告）日：1977-03-15

  Indole derivatives characterized by having a 1,3,4,9-tetrahydropyrano[3,4-b]indole or 1,3,4,9-tetrahydrothiopyrano[3,4-b]indole nucleus bearing a substituent in position 1, said substituent incorporating an acid, ester or amide function therein, are disclosed. The nucleus is further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7, 8, and 9. The derivatives are useful antiinflammatory, analgesic, antibacterial and antifungal agents and methods for their preparation and use are also disclosed.

  本发明涉及一种1,3,4,9-四氢吡喃并[3,4-b]吲哚或1,3,4,9-四氢噻吩并[3,4-b]吲哚核，在1号位置带有一个包含酸、酯或酰胺功能的取代基的吲哚衍生物。该核在1号位置进一步取代，可选择在3、4、5、6、7、8和9号位置进一步取代。这些衍生物是有用的抗炎、镇痛、抗菌和抗真菌剂，还公开了它们的制备和使用方法。
• Pharmaceutical method for using pyrano-and thiopyranoindole derivatives
  申请人：Ayerst McKenna and Harrison Ltd.

  公开号：US04041169A1

  公开（公告）日：1977-08-09

  Pyranoindole and thiopyranoindole derivatives characterized by having an amino(lower)alkyl radical attached to either or both the 1 and 9 position of a pyrano[3,4-b]indole or thiopyrano[3,4-b]indole nucleus or having said radical attached to the 1 position of a pyrano[4,3-b]indole or thiopyrano[4,3-b]indole nucleus are disclosed. The amino portion of the amino(lower)alkyl radical may be further substituted with one or two lower alkyl groups or incorporated into a heterocyclic amine radical. The derivatives having the amino(lower)alkyl radical only at position 1 are further substituted at position 1 and may be optionally substituted at positions 3,4,5,6,7,8, and 9. The pyrano[3,4-b]indole or thiopyrano[3,4-b]indole derivatives having the amino(lower)alkyl radical only at position 9 possess two substituents at position 1 and may be optionally substituted at position 3,4,5,6,7, and 8; the derivatives having an amino(lower)alkyl radical at both positions 1 and 9 are further substituted at position 1 and may be optionally substituted at positions 3,4,5,6,7 and 8. The pyrano- and thiopyranoindole derivatives of this invention are useful antidepressant and antiulcer agents. Methods for the preparation and use of these derivatives are also disclosed.

  本发明揭示了一种带有氨基（较低）烷基基团的吡喃并[3,4-b]吲哚或硫代吡喃并[3,4-b]吲哚核的衍生物，其中该基团连接到1和/或9位，或连接到吡喃并[4,3-b]吲哚或硫代吡喃并[4,3-b]吲哚核的1位。氨基（较低）烷基基团的氨基部分可以进一步取代为一个或两个较低的烷基基团或并入到一个杂环胺基团中。仅在1位具有氨基（较低）烷基基团的衍生物在1位进一步取代，并可在3、4、5、6、7、8和9位选择性地取代。仅在9位具有氨基（较低）烷基基团的吡喃并[3,4-b]吲哚或硫代吡喃并[3,4-b]吲哚衍生物在1位具有两个取代基，并可在3、4、5、6、7和8位选择性地取代；在1和9位均具有氨基（较低）烷基基团的衍生物在1位进一步取代，并可在3、4、5、6、7和8位选择性地取代。本发明的吡喃并和硫代吡喃并吲哚衍生物是有用的抗抑郁和抗溃疡药物。还揭示了这些衍生物的制备和使用方法。