2-[2-(1H-indol-3-yl)ethyl]-2-azabicyclo[2.2.2]oct-5-ene | 61088-68-4

• 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: 2-[2-(1H-indol-3-yl)ethyl]-2-azabicyclo[2.2.2]oct-5-ene
• 英文别名: 2-(2-indol-3-yl-ethyl)-2-aza-bicyclo[2.2.2]oct-5-ene；3-(2-N-isoquinuclidinyl-ethyl)-indole；3-[2-(2-Azabicyclo[2.2.2]oct-5-en-2-yl)ethyl]-1H-indole
• CAS: 61088-68-4
• 化学式: C₁₇H₂₀N₂
• 分子量: 252.359
• InChiKey: FPYYJCSWTPGTAY-UHFFFAOYSA-N

物化性质

• 沸点：
  429.2±30.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-(2-溴乙基)吲哚 在 六甲基磷酰三胺 、 lithium thiopropiolate 作用下， 以 乙醇 为溶剂， 生成 2-[2-(1H-indol-3-yl)ethyl]-2-azabicyclo[2.2.2]oct-5-ene
  参考文献：
  名称：

  Tomisawa, Hiroshi; Hongo, Hiroshi; Kato, Hideki, Heterocycles, 1981, vol. 16, # 11, p. 1947 - 1950

  摘要：

  DOI：

文献信息

• [EN] SMALL MOLECULE INDUCERS OF GDNF AS POTENTIAL NEW THERAPEUTICS FOR NEUROPSYCHIATRIC DISORDERS<br/>[FR] PETITES MOLÉCULES INDUCTRICES DE GDNF COMME NOUVELLE THÉRAPEUTIQUE POSSIBLE DES TROUBLES NEUROPSYCHIATRIQUES
  申请人：UNIV COLUMBIA

  公开号：WO2013028999A1

  公开（公告）日：2013-02-28

  The invention provides a compound having the structure (I), wherein A is a substituted or unsubstituted ring; Z is present or absent and when present is (II), wherein n is 0, 1, 2, 3, or 4; Y is -(CR11R12)-, -NH(CR11R12)- or -O(CR11R12)- wherein R11 and R12 are each hydrogen or combine to form a carbonyl; and wherein R1 to R10 are herein as described.

  本发明提供了一种具有结构（I）的化合物，其中A是取代的或未取代的环；Z是否存在，如果存在则为（II），其中n为0，1，2，3或4；Y是-(CR11R12)-，-NH(CR11R12)-或-O(CR11R12)-，其中R11和R12分别是氢或结合形成一个羰基；以及其中R1至R10如本文所述。
• Lewis-acid catalysed tandem reaction Diels–Alder–[3,3] sigmatropic shift between buta-1,3-dienyl thiocyanic acid ester and acryloyl chloride: application in the synthesis of 2-azabicyclo[2.2.2]oct-5-ene derivatives
  作者：Joseph Schoepfer、Christian Marquis、Cécile Pasquier、Reinhard Neier

  DOI：10.1039/c39940001001

  日期：——

  Buta-1,3-dienyl thiocyanic acid ester reacts with acryloyl chloride in presence of Lewis acid catalysts to produce directly the rearranged product of type 3bvia a combination of a Diels-Alder reaction with a [3,3] sigmatropic shift; the 1,4-substituted cyclohexene is easily transformed into the 2-azabicyclo[2.2.2]oct-5-ene derivative 6b, which has been used as precursor for the synthesis of the Ibogamin

  Buta-1,3-二烯硫氰酸酯在路易斯酸催化剂的存在下与丙烯酰氯反应，通过Diels-Alder反应与[3,3]σ位移的组合直接产生3b型重排产物；1,4-取代的环己烯很容易转化为2-氮杂双环[2.2.2]辛-5-烯衍生物6b，该衍生物已用作合成伊博加明骨架的前体。
• Shoepfer Joseph, Marquis Christian, Pasquier Cecile, Neier Reinhard, J. Chem. Soc. Chem. Commun, (1994) N 8, S 1001-1002
  作者：Shoepfer Joseph, Marquis Christian, Pasquier Cecile, Neier Reinhard

  DOI：——

  日期：——
• SMALL MOLECULE INDUCERS OF GDNF AS POTENTIAL NEW THERAPEUTICS FOR NEUROPSYCHIATRIC DISORDERS
  申请人：Sames Dalibor

  公开号：US20150056699A1

  公开（公告）日：2015-02-26

  This invention provides a compound having the structure wherein A is a ring structure, with or without substitution; Z is present or absent and when present is wherein n is 0, 1, 2, 3, or 4; Y is —(CR 11 R 12 )—, —NH(CR 11 R 12 )—, or —O(CR 11 R 12 )—, wherein R 11 and R 12 are each hydrogen or combine to form a carbonyl; R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted heteroaryl, hydroxyl, amino, ester or amide; α represents a bond, which is present or absent and when α is present, then R 7 and R 8 are absent; R 7 and R 8 are present when α is absent and are independently H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted heteroaryl, hydroxyl, amino, ester, amide or R 5 and R 7 combine to form a carbonyl or R 6 and R 8 combine to form a carbonyl; R 9 and R 10 are each hydrogen or combine to form a carbonyl; and when α is present, Z is where n=1, Y is —(CR 11 R 12 )— where R 11 and R 12 are H, A is unsubstituted indole attached at the 3-position of the indole, R 3 , R 4 , R 5 , R 6 , R 9 and R 10 are each H, and one of R 1 or R 2 is H, then the other one of R 1 or R 2 is other than H or ethyl, or a pharmaceutically acceptable salt, diastereomer, or enantiomer thereof.
• US9988377B2
  申请人：——

  公开号：US9988377B2

  公开（公告）日：2018-06-05