2-(2-(hydroxymethyl)phenyl)-3,4-dihydroisoquinolin-1(2H)-one | 1428725-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(2-(hydroxymethyl)phenyl)-3,4-dihydroisoquinolin-1(2H)-one
• 英文别名: 2-[2-(Hydroxymethyl)phenyl]-3,4-dihydroisoquinolin-1-one；2-[2-(hydroxymethyl)phenyl]-3,4-dihydroisoquinolin-1-one
• CAS: 1428725-78-3
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: TWJDBXXQXSUJTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-(hydroxymethyl)phenyl)-3,4-dihydroisoquinolin-1(2H)-one 、 乙酸酐 在 scandium tris(trifluoromethanesulfonate) 作用下， 以90%的产率得到2-(1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)benzyl acetate
  参考文献：
  名称：

  Visible light photooxidative cyclization of amino alcohols to 1,3-oxazines

  摘要：

  1,3-Amino alcohols were prepared to examine how structure affects the oxidation of tertiary amines in visible light photocatalysis. These substrates were cyclized to produce oxazines following the photooxidative formation of iminium ions using catalytic Ru(bpy)(3)Cl-2. Amino alcohol derivatives of tetrahydroisoquinoline, tetrahydroquinoline, pyrrolidine, and Delta(3)-piperidine all were found to be viable substrates. In the case of the unsaturated piperidines, cyclization is accompanied by addition of methanol across the alkene; most likely occurring via a conjugate addition to an intermediate alpha,beta-unsaturated iminium ion prior to oxazine formation. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.031
• 作为产物：
  描述：

  2-(3,4-dihydroisoquinolin-2(1H)-yl)benzaldehyde 在 lithium aluminium tetrahydride 、 tris(bipyridine)ruthenium(II) dichloride hexahydrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.0h， 生成 2-(2-(hydroxymethyl)phenyl)-3,4-dihydroisoquinolin-1(2H)-one
  参考文献：
  名称：

  Visible light photooxidative cyclization of amino alcohols to 1,3-oxazines

  摘要：

  1,3-Amino alcohols were prepared to examine how structure affects the oxidation of tertiary amines in visible light photocatalysis. These substrates were cyclized to produce oxazines following the photooxidative formation of iminium ions using catalytic Ru(bpy)(3)Cl-2. Amino alcohol derivatives of tetrahydroisoquinoline, tetrahydroquinoline, pyrrolidine, and Delta(3)-piperidine all were found to be viable substrates. In the case of the unsaturated piperidines, cyclization is accompanied by addition of methanol across the alkene; most likely occurring via a conjugate addition to an intermediate alpha,beta-unsaturated iminium ion prior to oxazine formation. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.031

文献信息

• Visible light photooxidative cyclization of amino alcohols to 1,3-oxazines
  作者：Cheryl L. Mathis、Brandi M. Gist、Conerd K. Frederickson、Katie M. Midkiff、Christopher C. Marvin

  DOI：10.1016/j.tetlet.2013.02.031

  日期：2013.4

  1,3-Amino alcohols were prepared to examine how structure affects the oxidation of tertiary amines in visible light photocatalysis. These substrates were cyclized to produce oxazines following the photooxidative formation of iminium ions using catalytic Ru(bpy)(3)Cl-2. Amino alcohol derivatives of tetrahydroisoquinoline, tetrahydroquinoline, pyrrolidine, and Delta(3)-piperidine all were found to be viable substrates. In the case of the unsaturated piperidines, cyclization is accompanied by addition of methanol across the alkene; most likely occurring via a conjugate addition to an intermediate alpha,beta-unsaturated iminium ion prior to oxazine formation. (c) 2013 Elsevier Ltd. All rights reserved.