Methyl 1-(2-propenyl)-1H-indole-3-carboxylate | 133835-09-3

• 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: Methyl 1-(2-propenyl)-1H-indole-3-carboxylate
• 英文别名: methyl 1-allyl-1H-indole-3-carboxylate；Methyl 1-prop-2-enylindole-3-carboxylate
• CAS: 133835-09-3
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: WYBLUQMLFMNSPY-UHFFFAOYSA-N

物化性质

• 熔点：
  45.5-46.5 °C(Solv: hexane (110-54-3))
• 沸点：
  344.1±25.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-(2-(1-(tert-butylcarbamoyl)-5,6,7-trimethoxy-4-methylisoquinolin-2(1H)-yl)-2-oxoethyl) O-ethyl carbonodithioate 、 Methyl 1-(2-propenyl)-1H-indole-3-carboxylate 在 过氧化双月桂酰 作用下， 以 1,2-二氯乙烷 为溶剂， 以39%的产率得到methyl 1-((6-(tert-butylcarbamoyl)-8,9,10-trimethoxy-11-methyl-4-oxo-1,3,4,6-tetrahydro-2H-pyrido[1,2-b]isoquinolin-1-yl)methyl)-1H-indole-3-carboxylate
  参考文献：
  名称：

  Synthesis of Tetrahydro‐4 H ‐pyrido[1,2‐ b ]isoquinolin‐4‐ones from Ugi 4‐CR‐Derived Dihydroisoquinoline‐Xanthates**

  摘要：

  AbstractAn efficient protocol for the synthesis of poly‐functionalized 1,2,3,6‐tetrahydro‐4H‐pyrido[1,2‐b]isoquinolin‐4‐ones is described. First, propargyl‐containing Ugi adducts were transformed to polysubstituted dihydroisoquinolines by an intramolecular Au‐catalyzed alkyne hydro‐arylation, followed by the alkene isomerization process. Then, these pivotal intermediates were engaged in a xanthate‐based oxidative radical cascade addition/cyclization process with a suitable alkene.

  DOI：

  10.1002/ejoc.202200080
• 作为产物：
  描述：

  吲哚-3-甲酸甲酯 、 3-溴丙烯 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 以90%的产率得到Methyl 1-(2-propenyl)-1H-indole-3-carboxylate
  参考文献：
  名称：

  通过氧化级联加成/双环化自由基过程快速合成苦参碱类似物

  摘要：

  将烟酸酯-黄原酸酯衍生物添加到 N-烯丙基吲哚和 N-烯丙基吡咯，通过串联自由基分子间/分子内氧化加成反应序列生成多环杂环稠合的吡啶并萘啶，该反应序列在单个事件中产生三个新的 C-C 键和两个新环. 这种多杂环展示了苦参碱生物碱骨架，类似于吲哚-单萜类天然产物。

  DOI：

  10.1002/ejoc.201700208

文献信息

• A one-pot access to cycloalkano[1,2-a]indoles through an intramolecular alkyl migration reaction in indolylborates
  作者：Minoru Ishikura、Wataru Ida、Kazuo Yanada

  DOI：10.1016/j.tet.2005.10.045

  日期：2006.1

  protocol for the preparation of cycloalkano[1,2-a]indoles by way of an intramolecular alkyl migration reaction in cyclic indolylborates is described. NaOMe was found to act as a successful trialkylboryl-protecting group against to the lithiation at the C2 of the indole ring. Treatment of cyclic indolylborates with electrophiles produced cycloalkano-[1,2-a]indoles.

  描述了一种新颖的一锅法，用于通过环状吲哚硼酸酯中的分子内烷基迁移反应制备环烷[1,2- a ]吲哚。发现NaOMe可作为成功的三烷基硼基保护基团来抵抗吲哚环C2上的锂化。用亲电试剂处理环状吲哚硼酸酯产生环烷-[1,2- a ]吲哚。
• A new route to 9,9a-Dihydro-3H-pyrrolo[1,2-a]indoles via radical cyclization
  作者：Frederick E. Ziegler、Lucio O. Jeroncic

  DOI：10.1021/jo00011a008

  日期：1991.5

  A new method for the preparation of 9,9a-dihydro-3H-pyrrolo[1,2-a]indoles, an important substructure for the synthesis of mitomycins, is presented. A number of representative indoles are allylated on nitrogen with 1,3-dihalopropenes followed by n-Bu3SnH-mediated radical cyclization. The effect of the substitution patterns of the indoles and reaction conditions is explored. In all reactions the products of cyclization predominate; however, uncyclized materials are produced along with isomers and oxidation products of the cyclized substances.
• ZIEGLER, FREDERICK E.;JERONCIC, LUCIO O., J. ORG. CHEM., 56,(1991) N1, C. 3479-3486
  作者：ZIEGLER, FREDERICK E.、JERONCIC, LUCIO O.

  DOI：——

  日期：——