1-methyl-1,3,4,9-tetrahydropyrano<3,4-b>indol-1-carboxaldehyd | 41339-89-3

• 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>indol-1-carboxaldehyd
• 英文别名: 1-METHYL-1,3,4,9-TETRAHYDROPYRANO[3,4-b]INDOLE-1-CARBOXALDEHYDE；1-methyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indole-1-carbaldehyde；1-METHYL-1,3,4,9-TETRAHYDROPYRANO[3,4-b]INDOLE-1-CARBOXYALDEHYDE；1-methyl-4,9-dihydro-3H-pyrano[3,4-b]indole-1-carbaldehyde
• CAS: 41339-89-3
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: HXZXUULJTVBLDD-UHFFFAOYSA-N

物化性质

• 沸点：
  403.4±45.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-1,3,4,9-tetrahydropyrano<3,4-b>indol-1-carboxaldehyd 以 甲醇 为溶剂， 生成 1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-carboxaldehyde oxime
  参考文献：
  名称：

  Pyranoindole derivatives as antiulcer agents

  摘要：

  Pyranoindole和thiopyranoindole衍生物的特征在于在pyrano[3,4-b]indole或thiopyrano[3,4-b]indole核的1和9位置之一或两者上附加有氨基(较低)烷基基团，或者在pyrano[4,3-b]indole或thiopyrano[4,3-b]indole核的1位置上附加有该基团。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。只在位置1具有氨基(较低)烷基基团的衍生物在位置1进一步被取代，并且可以选择在位置3,4,5,6,7,8和9处被取代。只在位置9具有氨基(较低)烷基基团的pyrano[3,4-b]indole或thiopyrano[3,4-b]indole衍生物在位置1处具有两个取代基，并且可以选择在位置3,4,5,6,7和8处被取代；在位置1和9处都具有氨基(较低)烷基基团的衍生物在位置1处进一步被取代，并且可以选择在位置3,4,5,6,7和8处被取代。本发明的pyrano和thiopyranoindole衍生物可用作抗抑郁和抗溃疡剂。还公开了这些衍生物的制备和使用方法。

  公开号：

  US04066780A1
• 作为产物：
  描述：

  色醇 、 过氧化乙酰丙酮 在 对甲苯磺酸 作用下， 以 水 、 乙酸乙酯 、 苯 为溶剂， 生成 1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-methanol acetate 、 1-methyl-1,3,4,9-tetrahydropyrano<3,4-b>indol-1-carboxaldehyd
  参考文献：
  名称：

  1,3,4,9-Tetrahydropyrano[3,4-b]indole-1-acetamides and derivatives

  摘要：

  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。

  公开号：

  US03974179A1

文献信息

• Pyrano- and thiopyranoindole derivatives, compositions and methods of use
  申请人：Ayerst McKenna and Harrison Ltd.

  公开号：US04003913A1

  公开（公告）日：1977-01-18

  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。
• 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。
• Process for making pyrano- and thiopyranoindole derivatives
  申请人：Ayerst McKenna and Harrison Ltd.

  公开号：US04056537A1

  公开（公告）日：1977-11-01

  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 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 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.

  本发明披露了一种具有氨基（较低）烷基基团附加到吡喃[3,4-b]吲哚或硫代吡喃[3,4-b]吲哚核的1和9位置中的一个或两个的吡喃吲哚和硫代吡喃吲哚衍生物。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一个杂环胺基团中。仅在位置1具有氨基（较低）烷基基团的衍生物在位置1进一步取代，并且可以在位置3、4、5、6、7、8和9选择性地取代。仅在位置9具有氨基（较低）烷基基团的衍生物在位置1具有两个取代基，并且可以在位置3、4、5、6、7和8选择性地取代。在位置1和9均具有氨基（较低）烷基基团的衍生物在位置1进一步取代，并且可以在位置3、4、5、6、7和8选择性地取代。本发明的吡喃和硫代吡喃吲哚衍生物是有用的抗抑郁和抗溃疡药物。还披露了这些衍生物的制备和使用方法。
• Process for preparing pyrano- and thiopyranoindole derivatives
  申请人：Ayerst, McKenna & Harrison Limited

  公开号：US04056538A1

  公开（公告）日：1977-11-01

  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 are disclosed. The amino position 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 derivatives having the amino(lower)alkyl radical only at position 9 posses 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.

  本发明揭示了一种具有氨基（较低）烷基基团附加到吡喃[3,4-b]吲哚或硫代吡喃[3,4-b]吲哚核的1和9位置中的一种或两种的吡喃吲哚和硫代吡喃吲哚衍生物。氨基（较低）烷基基团的氨基位置可以进一步用一或两个较低烷基基团取代或并入杂环胺基团。仅在1位置具有氨基（较低）烷基基团的衍生物在1位置进一步取代，并可在3、4、5、6、7、8和9位置选择性地取代。仅在9位置具有氨基（较低）烷基基团的衍生物在1位置具有两个取代基，并可在3、4、5、6、7和8位置选择性地取代。同时在1和9位置具有氨基（较低）烷基基团的衍生物在1位置进一步取代，并可在3、4、5、6、7和8位置选择性地取代。本发明的吡喃吲哚和硫代吡喃吲哚衍生物是有用的抗抑郁和抗溃疡药物。还揭示了制备和使用这些衍生物的方法。
• Pyranoindole derivatives, compositions and method of use
  申请人：Ayerst, McKenna and Harrison Ltd.

  公开号：US04066779A1

  公开（公告）日：1978-01-03

  Pyranolindole 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 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 thiopyranindole derivatives of this invention are useful antidepressant and antiulcer agents. Methods for the preparation and use of these derivatives are also disclosed.

  本发明揭示了具有氨基(较低)烷基基团结合到吡喃[3,4-b]吲哚或硫代吡喃[3,4-b]吲哚核的1和9位置之一或两个位置上，或者具有该基团结合到吡喃[4,3-b]吲哚或硫代吡喃[4,3-b]吲哚核的1位置的吡喃吲哚和硫代吡喃吲哚衍生物。氨基(较低)烷基基团的氨基部分可以进一步被一个或两个较低的烷基基团取代或并入到一个杂环胺基团中。仅在1位置具有氨基(较低)烷基基团的衍生物在1位置进一步取代，并且可以在3、4、5、6、7、8和9位置可选地取代。仅在9位置具有氨基(较低)烷基基团的吡喃[3,4-b]吲哚或硫代吡喃[3,4-b]吲哚衍生物在1位置具有两个取代基，并且可以在3、4、5、6、7和8位置可选地取代；在1和9位置都具有氨基(较低)烷基基团的衍生物在1位置进一步取代，并且可以在3、4、5、6、7和8位置可选地取代。本发明的吡喃和硫代吡喃吲哚衍生物是有用的抗抑郁和抗溃疡剂。本发明还揭示了这些衍生物的制备和使用方法。