1-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)cyclopropanol | 653579-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)cyclopropanol
• 英文别名: Cyclopropanol, 1-[(1,2,3,4-tetrahydro-1-isoquinolinyl)methyl]-；1-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)cyclopropan-1-ol
• CAS: 653579-36-3
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: UDLVJBVNERKCMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)cyclopropanol 在 palladium diacetate 吡啶 、 molecular sieve 、 氧气 作用下， 以 乙腈 为溶剂， 反应 20.0h， 生成 1,3,4,6,7,11b-hexahydro-2oxo-2H-benzo[a]quinolizine 、 1,6,7,11b-tetrahydro-2H-pyrido[2,1-a]isoquinolin-2-one
  参考文献：
  名称：

  Domino Palladium(II)-Mediated Rearrangement-Oxidative Cyclization of β-Aminocyclopropanols

  摘要：

  在由Pd(II)盐催化的多米诺反应中，β-氨基环丙醇被转化为相应的2,3-二氢-1H-吡啶-4-酮。相反，使用Pd(0)衍生物Pd(dba)2则可得到相应的四氢吡啶-4-酮。使用Pd(II)和Cu(OAc)2作为化学计量氧化剂，也能得到饱和衍生物，且产率更高。

  DOI：

  10.1055/s-2003-42122
• 作为产物：
  描述：

  3,4-dihydro-isoquinoline 2-oxide 在 samarium diiodide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 50.0h， 生成 1-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)cyclopropanol
  参考文献：
  名称：

  Two-Step Metal-Mediated Transformation of Isoxazolidine-5-spirocyclopropanes into Pyridone Derivatives

  摘要：

  The two-step metal-catalyzed overall transformation of isoxazolidine-5-spirocyclopropanes into the corresponding dihydro- and tetrahydropyridones is described. The first step is the chemoselective reduction of the N-O bond of the isoxazolidine ring preserving the fragile cyclopropanol moiety while the second transformation is the Pd(II) or Pd(O) conversion of the beta-aminocyclopropanol derivatives into the final compounds. The scope and limitations of this strategy are described.

  DOI：

  10.1021/jo050640q

文献信息

• Domino Palladium(II)-Mediated Rearrangement-Oxidative Cyclization of β-Aminocyclopropanols
  作者：Alberto Brandi、Stefano Cicchi、Julia Revuelta、Alessandra Zanobini、Matteo Betti

  DOI：10.1055/s-2003-42122

  日期：——

  β-Aminocyclopropanols were transformed, in a domino process catalyzed by Pd(II) salts, into the corresponding 2,3-dihydro-1H-pyridin-4-ones. Conversely the use of a Pd(0) derivative, Pd(dba)2, afforded the corresponding tetrahydropyrid-4-ones. The saturated derivatives were also obtained, in better yields, using Pd(II) and Cu(OAc)2 as stoichiometric oxidant.

  在由Pd(II)盐催化的多米诺反应中，β-氨基环丙醇被转化为相应的2,3-二氢-1H-吡啶-4-酮。相反，使用Pd(0)衍生物Pd(dba)2则可得到相应的四氢吡啶-4-酮。使用Pd(II)和Cu(OAc)2作为化学计量氧化剂，也能得到饱和衍生物，且产率更高。
• Samarium(II) iodide reduction of isoxazolidines
  作者：Julia Revuelta、Stefano Cicchi、Alberto Brandi

  DOI：10.1016/j.tetlet.2004.09.050

  日期：2004.11

  SmI2 was used as reducing agent for the N-O bond cleavage in isoxazolidines. The procedure revealed is general and particularly useful for the transformation of 5-spirocyclopropane isoxazolidines to the corresponding beta-aminocyclopropanols, a troublesome transformation with other known reagents. (C) 2004 Elsevier Ltd. All rights reserved.
• Two-Step Metal-Mediated Transformation of Isoxazolidine-5-spirocyclopropanes into Pyridone Derivatives
  作者：Julia Revuelta、Stefano Cicchi、Alberto Brandi

  DOI：10.1021/jo050640q

  日期：2005.7.1

  The two-step metal-catalyzed overall transformation of isoxazolidine-5-spirocyclopropanes into the corresponding dihydro- and tetrahydropyridones is described. The first step is the chemoselective reduction of the N-O bond of the isoxazolidine ring preserving the fragile cyclopropanol moiety while the second transformation is the Pd(II) or Pd(O) conversion of the beta-aminocyclopropanol derivatives into the final compounds. The scope and limitations of this strategy are described.