tert-butyl indole-4-carboxylate | 741606-19-9

• 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 indole-4-carboxylate
• 英文别名: tert-butyl 1H-indole-4-carboxylate
• CAS: 741606-19-9
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: MMAGWAVWHXWHAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl indole-4-carboxylate 在 乙酸酐 、 sodium hydride 、 二甲基亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 tert-butyl 1-[3-(4-octylphenoxy)-2-oxopropyl]indole-4-carboxylate
  参考文献：
  名称：

  Design and Synthesis of 1-Indol-1-yl-propan-2-ones as Inhibitors of Human Cytosolic Phospholipase A₂α

  摘要：

  The synthesis and structure-activity relationship study of a series of 1-indol-1-yl-3-phenoxypropan-2-one inhibitors of cytosolic phospholipase A(2)alpha (cPLA(2)alpha) are described. The compounds were evaluated in a vesicle assay with isolated cPLA(2)alpha and in cellular assays with intact human platelets. Systematic variation led to 3-methylhydrogen 1-[3-(4-decyloxyphenoxy)-2-oxopropyl]indole-3,5-dicarboxylate (57), which revealed the highest activity against the isolated enzyme. With an IC50 value of 4.3 nM in this assay, it is one of the most potent in vitro cPLA(2)alpha inhibitors known today.

  DOI：

  10.1021/jm051243a
• 作为产物：
  描述：

  吲哚-4-羧酸 、 N,N-二甲基甲酰胺二叔丁基缩醛 以 苯 为溶剂， 以56%的产率得到tert-butyl indole-4-carboxylate
  参考文献：
  名称：

  Convenient Synthesis of Pyrrole‐ and Indolecarboxylic Acid tert‐Butylesters

  摘要：

  The tert-butylesters of pyrrole- and indolecarboxylic acids are readily accessed by reacting the appropriate carboxylic acids with N,N-dimethyl-formamide di-tert-butyl acetal.

  DOI：

  10.1081/scc-200032421

文献信息

• Rhodium-Catalyzed Regioselective C7-Functionalization of <i>N</i> -Pivaloylindoles
  作者：Lanting Xu、Chao Zhang、Yupeng He、Lushi Tan、Dawei Ma

  DOI：10.1002/anie.201508117

  日期：2016.1.4

  efficient rhodium‐catalyzed method for direct CH functionalization at the C7 position of a wide range of indoles has been developed. Good to excellent yields of alkenylation products were observed with acrylates, styrenes, and vinyl phenyl sulfones, whereas the saturated alkylation products were obtained in good yield with α,β‐unsaturated ketones. Both the N‐pivaloyl directing group and the rhodium catalyst

  已经开发了一种有效的铑催化方法，用于在多种吲哚的C7位直接进行CH功能化。丙烯酸酯，苯乙烯和乙烯基苯基砜的链烯基化产物收率良好至优异，而α，β-不饱和酮的饱和烷基化产物收率高。两者Ñ -pivaloyl导向基团和铑催化剂被证明是高区域选择性和转化率的关键。
• Convenient Synthesis of Pyrrole‐ and Indolecarboxylic Acid <i>tert</i>‐Butylesters
  作者：Joachim Ludwig、Matthias Lehr

  DOI：10.1081/scc-200032421

  日期：2004.1.1

  The tert-butylesters of pyrrole- and indolecarboxylic acids are readily accessed by reacting the appropriate carboxylic acids with N,N-dimethyl-formamide di-tert-butyl acetal.
• Design and Synthesis of 1-Indol-1-yl-propan-2-ones as Inhibitors of Human Cytosolic Phospholipase A₂α
  作者：Joachim Ludwig、Stefanie Bovens、Carsten Brauch、Alwine Schulze Elfringhoff、Matthias Lehr

  DOI：10.1021/jm051243a

  日期：2006.4.1

  The synthesis and structure-activity relationship study of a series of 1-indol-1-yl-3-phenoxypropan-2-one inhibitors of cytosolic phospholipase A(2)alpha (cPLA(2)alpha) are described. The compounds were evaluated in a vesicle assay with isolated cPLA(2)alpha and in cellular assays with intact human platelets. Systematic variation led to 3-methylhydrogen 1-[3-(4-decyloxyphenoxy)-2-oxopropyl]indole-3,5-dicarboxylate (57), which revealed the highest activity against the isolated enzyme. With an IC50 value of 4.3 nM in this assay, it is one of the most potent in vitro cPLA(2)alpha inhibitors known today.