tert-butyl (2-(3-methoxy-1-methyl-2-oxoindolin-3-yl)ethyl)carbamate | 1280219-54-6

• 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: tert-butyl (2-(3-methoxy-1-methyl-2-oxoindolin-3-yl)ethyl)carbamate
• 英文别名: tert-butyl N-[2-(3-methoxy-1-methyl-2-oxoindol-3-yl)ethyl]carbamate
• CAS: 1280219-54-6
• 化学式: C₁₇H₂₄N₂O₄
• 分子量: 320.389
• InChiKey: KSHRCLBQUHKXPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-(3-methoxy-1-methyl-2-oxoindolin-3-yl)ethyl)carbamate 在 红铝 作用下， 以 甲苯 为溶剂， 反应 13.5h， 以75%的产率得到cis-1,2,3,3a,8,8a-hexahydro-3a-methoxy-1,8-dimethylpyrrolo[2,3-b]indole
  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
• 作为产物：
  描述：

  3-亚甲基氧化吲哚 在 sodium tetrahydroborate 、 potassium acetate 、 caesium carbonate 、 nickel dichloride 作用下， 以 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 21.0h， 生成 tert-butyl (2-(3-methoxy-1-methyl-2-oxoindolin-3-yl)ethyl)carbamate
  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

• Di-<i>tert</i>-butyl Ethynylimidodicarbonate as a General Synthon for the β-Aminoethylation of Organic Electrophiles: Application to the Formal Synthesis of Pyrrolidinoindoline Alkaloids (±)-CPC-1 and (±)-Alline
  作者：Ramsay E. Beveridge、Yiwei Hu、Bruce Gregoire、Robert A. Batey

  DOI：10.1021/acs.joc.0c00781

  日期：2020.7.2

  β-aminoethyl anion synthetic equivalent. It can be used to install ethyleneamine groups by exploiting its terminal alkyne reactivity with common organic electrophiles. Reactions exemplified with this terminal ynimide reagent include additions to imines, aldehydes, ketones, pyridinium salts, Michael acceptors, epoxides, and Pd-catalyzed Sonogashira couplings. Subsequent regioselective [3 + 2] cycloadditions

  乙二胺基二碳酸二叔丁酯已证明是β-氨乙基阴离子合成的等价物。通过利用其与常见有机亲电子试剂的末端炔反应性，可用于安装亚乙基胺基。以该末端酰亚胺酰亚胺试剂为例的反应包括添加至亚胺，醛，酮，吡啶鎓盐，迈克尔受体，环氧化物和Pd催化的Sonogashira偶联。炔基酰亚胺（酰亚胺）的随后区域选择性[3 + 2]环加成反应生成N，N -N-二-Boc酰亚胺官能化的三唑和异恶唑杂环。用Pd催化的加氢还原酰亚胺可生成具有易于去除的N，N的乙二酰亚胺-di-Boc-氨基甲酸酯保护基团，允许使用基于酰亚胺的灵活方法来安装亚乙基胺。在吡咯烷二氢吲哚啉生物碱（±）-CPC-1和（±）-alline的简短形式合成中证明了这种两步氨基乙基化策略的效用。类似地，试剂（N，N，N '）-三-Boc 2-乙炔基肼用作β-肼基乙基阴离子合成当量。
• 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.