5-bromo-2,3-dihydro-Nb-methoxycarbonyltryptamine | 88369-00-0

• 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: 5-bromo-2,3-dihydro-Nb-methoxycarbonyltryptamine
• 英文别名: methyl N-[2-(5-bromo-2,3-dihydro-1H-indol-3-yl)ethyl]carbamate
• CAS: 88369-00-0
• 化学式: C₁₂H₁₅BrN₂O₂
• 分子量: 299.167
• InChiKey: BIQLWQOGVLKFMA-UHFFFAOYSA-N

物化性质

• 沸点：
  403.3±45.0 °C(Predicted)
• 密度：
  1.400±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-2,3-dihydro-Nb-methoxycarbonyltryptamine 在 sodium tungstate 、 双氧水 作用下， 以57%的产率得到氨甲酸,[2-(5-溴-1-羟基-1H-吲哚-3-基)乙基]-,甲基酯
  参考文献：
  名称：

  Preparations of 1-Hydroxyindole Derivatives and Their Potent Inhibitory Activities on Platelet Aggregation

  摘要：

  1-Hydroxymelatonin, 5-bromo- and 5,7-dibromo-1-hydroxytryptamine derivatives, 1,4-dihydroxy-5-nitroindole, 1-hydroxy-3-methylsulfinylmethylindole, and 5-acetyl-1,3,4,5-tetrahydro-1-hydroxypyrrolo[4,3,2-de]quinoline were synthesized for the first time, 1-Hydroxyindoles revealed potent inhibitory activities on platelet aggregation.

  DOI：

  10.3987/com-96-7537
• 作为产物：
  描述：

  1-hydroxy-Nb-methoxycarbonyltryptamine 在 溴 、 三溴化硼 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 1.0h， 生成 5-bromo-2,3-dihydro-Nb-methoxycarbonyltryptamine
  参考文献：
  名称：

  A Novel Methodology for Preparing 5-Chloro- and 5-Bromotryptamines and Tryptophanes, and Its Application to the Synthesis of (±)-Bromochelonin B

  摘要：

  DOI：

  10.3987/com-99-8721

文献信息

• C 2-Symmetric Chiral Sulfoxide-Mediated Intermolecular Interrupted Pummerer Reaction for Enantioselective Construction of C3a-Substituted Pyrroloindolines
  作者：Kazuhiro Higuchi、Tomomi Kawasaki、Masanori Tayu、Yui Suzuki

  DOI：10.1055/s-0035-1560548

  日期：——

  The first example of an enantioselective intermolecular interrupted Pummerer reaction has been developed by the utilization of a C 2-symmetric chiral sulfoxide. The reaction was used for the enantioselective synthesis of C3a-substituted pyrroloindolines in a one-pot procedure starting from tryptamine. The synthetic utility of the reaction was further demonstrated by its application to the highly concise

  对映选择性分子间间断Pummerer 反应的第一个例子是利用C 2 对称手性亚砜开发的。该反应用于在从色胺开始的一锅法中对映选择性合成 C3a 取代的吡咯并二氢吲哚。该反应在 (+)-psychotriasine 的高度简洁全合成中的应用进一步证明了该反应的合成效用。
• DMSO/Tf₂O-mediated cross-coupling of tryptamine with substituted aniline to access C3a–N1′-linked pyrroloindoline alkaloids
  作者：Masanori Tayu、Takako Ishizaki、Kazuhiro Higuchi、Tomomi Kawasaki

  DOI：10.1039/c5ob00190k

  日期：——

  The cross-coupling of tryptamine with substituted aniline to C3a–nitrogen-linked pyrroloindolines has been developedviathe consecutive cyclization of tryptamine with DMSO/Tf₂O and the substitution of 3a-pyrroloindolylthionium intermediate with aniline.

  已开发了将色胺与取代苯胺进行交叉偶联，形成C3a-氮键连结的吡咯吲哚类化合物，通过色胺与DMSO/Tf₂O的连续环化和3a-吡咯吲哚硫代阳离子中间体与苯胺的取代反应。
• Preparations of 1-Hydroxyindole Derivatives and Their Potent Inhibitory Activities on Platelet Aggregation
  作者：Masanori Somei、Koji Yamada、Masakazu Hasegawa、Mutsuko Tabata、Yoshiyuki Nagahama、Harunobu Morikawa、Fumio Yamada

  DOI：10.3987/com-96-7537

  日期：——

  1-Hydroxymelatonin, 5-bromo- and 5,7-dibromo-1-hydroxytryptamine derivatives, 1,4-dihydroxy-5-nitroindole, 1-hydroxy-3-methylsulfinylmethylindole, and 5-acetyl-1,3,4,5-tetrahydro-1-hydroxypyrrolo[4,3,2-de]quinoline were synthesized for the first time, 1-Hydroxyindoles revealed potent inhibitory activities on platelet aggregation.
• A Novel Methodology for Preparing 5-Chloro- and 5-Bromotryptamines and Tryptophanes, and Its Application to the Synthesis of (±)-Bromochelonin B
  作者：Masanori Somei、Masakazu Hasegawa、Koji Yamada、Yoshiyuki Nagahama

  DOI：10.3987/com-99-8721

  日期：——