2-(hydroxymethyl)-4,5,6,7-tetrahydro-3aH-isoxazole<2,3-a>pyridine | 134390-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-(hydroxymethyl)-4,5,6,7-tetrahydro-3aH-isoxazole<2,3-a>pyridine
• 英文别名: 4,5,6,7-tetrahydro-3aH-[1,2]oxazolo[2,3-a]pyridin-2-ylmethanol
• CAS: 134390-26-4
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: GORDSYHWMQPDEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  32.7
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2,3,4,5-四氢吡啶1-氧化物 在 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 2-(hydroxymethyl)-4,5,6,7-tetrahydro-3aH-isoxazole<2,3-a>pyridine
  参考文献：
  名称：

  (Nitroaryl)sulfinyl-substituted allenes. Novel and convenient propargyl alcohol synthons in 4 + 2 cycloaddition chemistry

  摘要：

  (Nitroaryl)sulfinyl-substituted allenes are conveniently prepared by treating propargyl alcohol or methyl 3-hydroxy-2-butynoate with a (nitroaryl)sulfenyl chloride and triethylamine. These activated allenes undergo 4 + 2 cycloaddition across the C1C2-pi-bond. The initially formed allylic sulfoxide readily undergoes a 2,3-sigmatropic rearrangement to produce a stable sulfenate ester that is easily cleaved with thiophilic reagents. The dienophilic reactivity of the (nitroary)sulfinyl-substituted allene is much greater than the corresponding propargyl alcohol, and the cycloaddition also proceeds with high regioselectivity. The Diels-Alder reaction of [(2-nitrophenyl)-sulfinyl]propadiene with Danishefsky's diene affords meta-substituted benzyl alcohols in high yield. Reaction of the more highly activated methyl 2-[(2-nitrophenyl)sulfinyl]-2,3-butadienoate with Danishefsky's diene followed by treatment of the resulting sulfenate ester with triethyl phosphite produces substituted phthalides in excellent yield. The (2,4-dinitrophenyl)sulfinyl-substituted allene was found to react smoothly with a variety of nitrones to give sulfenate esters of isoxazolidines. These allenyl sulfoxides correspond to formal equivalents of propargyl alcohol, which itself is too unreactive to undergo Diels-Alder chemistry or 1,3-dipolar cycloaddition with nitrones or nitrile oxides.

  DOI：

  10.1021/jo00013a033

文献信息

• PADWA, ALBERT;BULLOCK, WILLIAM H.;NORMAN, BRYAN H.;PERUMATTAM, JOHN, J. ORG. CHEM., 56,(1991) N3, C. 4252-4259
  作者：PADWA, ALBERT、BULLOCK, WILLIAM H.、NORMAN, BRYAN H.、PERUMATTAM, JOHN

  DOI：——

  日期：——