1-methyl-2,3,8,8a-tetrahydropyrrolo[2,3-b]indol-3a(1H)-ol | 101053-34-3

• 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-2,3,8,8a-tetrahydropyrrolo[2,3-b]indol-3a(1H)-ol
• 英文别名: 1-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-3a-ol；(+/-)-alline；(3aR,8aS)-2,3,8,8a-Tetrahydro-1-methylpyrrolo[2,3-b]indol-3a(1H)-ol；(3aS,8bR)-3-methyl-1,2,3a,4-tetrahydropyrrolo[2,3-b]indol-8b-ol
• CAS: 101053-34-3
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: CBQYNPHHHJTCJS-WDEREUQCSA-N

物化性质

• 沸点：
  345.9±42.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  35.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-亚甲基氧化吲哚 在 lithium aluminium tetrahydride 、 萘 、 potassium acetate 、 sodium 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 31.75h， 生成 1-methyl-2,3,8,8a-tetrahydropyrrolo[2,3-b]indol-3a(1H)-ol
  参考文献：
  名称：

  A [3 + 2] Dipolar Cycloaddition Route to 3-Hydroxy-3-alkyl Oxindoles: An Approach to Pyrrolidinoindoline Alkaloids

  摘要：

  A [3 + 2] cycloaddition approach to the 3-hydroxy-3-alkyl oxindole scaffold is described. Isoxazolines obtained by cycloaddition of nitrile oxide 3 with 3-methylene oxindoles were elaborated to 3-hydroxy-3-cyanomethyl oxindoles employing a one-pot protocol en route to the pyrrolidinoindoline moiety which is found in many natural products. The total syntheses of alkaloids (+/-)-alline and (+/-)-CPC-1 were achieved using this methodology.

  DOI：

  10.1021/ol200547m

文献信息

• Copper/Iodine Co-catalyzed Oxygenative Transannulation of Tryptamines Enables Direct Synthesis of Donaxaridine and Its Derivatives
  作者：Yan-Zheng Sun、Ying-Ai Wu、Jun Shi、Wei Wu、Jun-Rong Song、Hai Ren

  DOI：10.1021/acs.orglett.3c03942

  日期：2024.1.26

  transannulation strategy using readily available tryptamines. Molecular oxygen and water are used as oxygen sources and provide direct access to the donaxaridine scaffold and its derivatives. This methodology is applied to the efficient synthesis of the natural products donaxaridine, chimonamidine, donaxanine, donaxarine, and aline in just one or two steps. The tryptamines, albeit with oxy-sensitive dialkyl N-H

  我们报告了使用现成的色胺的一般铜/碘共催化含氧转环策略。分子氧和水用作氧源，并提供直接进入多那沙定支架及其衍生物的途径。该方法适用于仅通过一两个步骤即可有效合成天然产物多纳沙啶、chimonamidine、donaxanine、donaxarine 和 aline。色胺虽然具有氧敏感的二烷基N -H 基团，但通过单电子转移双氧化过程被选择性氧化。
• A [3 + 2] Dipolar Cycloaddition Route to 3-Hydroxy-3-alkyl Oxindoles: An Approach to Pyrrolidinoindoline Alkaloids
  作者：Anand Singh、Gregory P. Roth

  DOI：10.1021/ol200547m

  日期：2011.4.15

  A [3 + 2] cycloaddition approach to the 3-hydroxy-3-alkyl oxindole scaffold is described. Isoxazolines obtained by cycloaddition of nitrile oxide 3 with 3-methylene oxindoles were elaborated to 3-hydroxy-3-cyanomethyl oxindoles employing a one-pot protocol en route to the pyrrolidinoindoline moiety which is found in many natural products. The total syntheses of alkaloids (+/-)-alline and (+/-)-CPC-1 were achieved using this methodology.