4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-ethoxythiocarbonylsulfanyl-butyric acid methyl ester | 1180130-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-ethoxythiocarbonylsulfanyl-butyric acid methyl ester
• 英文别名: methyl 4-(1,3-dioxoisoindolin-2-yl)-4-((ethoxycarbonothioyl)thio)butanoate；Methyl 4-(1,3-dioxoisoindol-2-yl)-4-ethoxycarbothioylsulfanylbutanoate；methyl 4-(1,3-dioxoisoindol-2-yl)-4-ethoxycarbothioylsulfanylbutanoate
• CAS: 1180130-19-1
• 化学式: C₁₆H₁₇NO₅S₂
• 分子量: 367.447
• InChiKey: LHKAYUREZMKSAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  烯丙基磷酸二甲酯 、 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-ethoxythiocarbonylsulfanyl-butyric acid methyl ester 在 过氧化双月桂酰 作用下， 以 1,2-二氯乙烷 为溶剂， 生成
  参考文献：
  名称：

  Functional Primary Amines and Diamines from α-Aminoacids. A Concise Route to Substituted 2-Aminotetralins

  摘要：

  S-Phthalimidomethyl xanthates derived from various alpha-amino acids add efficiently to a range of unactivated alkenes to give a variety of highly functionalized, protected amines. In the case of phenylalanine and tyrosine derived xanthates, the adducts can be further converted into the rare 4-substituted 2-aminotetralines by a radical ring closure onto the aromatic ring.

  DOI：

  10.1021/ol901263t
• 作为产物：
  描述：

  C₁₇H₁₇NO₆S₂ 以 乙酸乙酯 为溶剂， 反应 1.0h， 以2.9 g的产率得到4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-ethoxythiocarbonylsulfanyl-butyric acid methyl ester
  参考文献：
  名称：

  Functional Primary Amines and Diamines from α-Aminoacids. A Concise Route to Substituted 2-Aminotetralins

  摘要：

  S-Phthalimidomethyl xanthates derived from various alpha-amino acids add efficiently to a range of unactivated alkenes to give a variety of highly functionalized, protected amines. In the case of phenylalanine and tyrosine derived xanthates, the adducts can be further converted into the rare 4-substituted 2-aminotetralines by a radical ring closure onto the aromatic ring.

  DOI：

  10.1021/ol901263t

文献信息

• Direct Decarboxylative Functionalization of Carboxylic Acids via O–H Hydrogen Atom Transfer
  作者：Christina G. Na、Davide Ravelli、Erik J. Alexanian

  DOI：10.1021/jacs.9b10825

  日期：2020.1.8

  Decarboxylative functionalization via hydrogen atom transfer offers an attractive alternative to standard redox approaches to this important class of transformations. Herein, we report a direct decarboxylative functionalization of aliphatic carboxylic acids using N-xanthylamides. The unique reactivity of amidyl radicals in hydrogen atom transfer enables decarboxylative xanthylation under redox-neutral

  通过氢原子转移进行的脱羧功能化为此类重要转化的标准氧化还原方法提供了一种有吸引力的替代方法。在此，我们报告了使用 N-黄原酰胺对脂肪族羧酸进行直接脱羧功能化。酰胺基自由基在氢原子转移中的独特反应性使得在氧化还原中性条件下脱羧黄嘌呤化成为可能。该平台通过黄药组的后续阐述提供了对一系列衍生物的便利访问。
• Functional Primary Amines and Diamines from α-Aminoacids. A Concise Route to Substituted 2-Aminotetralins
  作者：Béatrice Quiclet-Sire、Guillaume Revol、Samir Z. Zard

  DOI：10.1021/ol901263t

  日期：2009.8.20

  S-Phthalimidomethyl xanthates derived from various alpha-amino acids add efficiently to a range of unactivated alkenes to give a variety of highly functionalized, protected amines. In the case of phenylalanine and tyrosine derived xanthates, the adducts can be further converted into the rare 4-substituted 2-aminotetralines by a radical ring closure onto the aromatic ring.