4-溴芦竹碱 | 64258-88-4

• 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
• 中文名称: 4-溴芦竹碱
• 英文名称: 1-(4-bromo-1H-indol-3-yl)-N,N-dimethylmethanamine
• 英文别名: 4-bromogramine
• CAS: 64258-88-4
• 化学式: C₁₁H₁₃BrN₂
• 分子量: 253.142
• InChiKey: WJLZJGWWMSKGKY-UHFFFAOYSA-N

物化性质

• 熔点：
  146-147 °C(Solv: methanol (67-56-1))
• 沸点：
  346.9±27.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

SDS

4-溴芦竹碱MSDS英文版

反应信息

• 作为反应物：
  描述：

  4-溴芦竹碱 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 4-溴-3-碘吲哚-1-羧酸叔丁基酯
  参考文献：
  名称：

  Rapid Route to 3,4-Substituted Indoles via a Directed Ortho Metalation−Retro-Mannich Sequence

  摘要：

  [GRAPHICS]In the presence of NXS (X = Br, I, Cl), gramine derivatives 1, derived by combined directed ortho metalation (DoM)-cross-coupling sequences, rapidly undergo retro-Mannich fragmentation (2) to afford 3-halo indoles 3 in 37-88% yields. A conceptually new methodology to diverse 3,4-substituted indoles (10, 11, 13) is thereby introduced.

  DOI：

  10.1021/ol017310m
• 作为产物：
  描述：

  (4-bromo-1-triisopropylsilyl-1H-indol-3-ylmethyl)-dimethylamine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以99%的产率得到4-溴芦竹碱
  参考文献：
  名称：

  对映体合成的（R）-4-氨基-5-氧代-1,3,4,5-四氢苯并[cd]吲哚，一种含有麦角三环核的高级中间体。

  摘要：

  我们报告了（R）-4-氨基-5-氧代-1,3,4,5-四氢苯并[cd]吲哚的对映体特异性合成的新策略。该化合物是高级中间体，其中包含许多四环麦角生物碱的三环核心。我们的方法涉及从吲哚基锂物种与掩蔽的丝氨酸的偶联初始合成D-4-溴色氨酸。α-氨基位置被N-三苯甲基保护，确保在随后的有机金属环化反应中该位置的对映体完整性。通过用BOC基团保护吲哚氮或将α-氨基酮还原为相应的β-氨基醇，可实现三环的稳定。

  DOI：

  10.1021/jo981723s

文献信息

• The chemistry of indoles. XXIV. Syntheses of 3-indoleacetic acid and 3-indoleacetonitrile having a halogeno group and a carbon functional group at the 4-position.
  作者：MASANORI SOMEI、KIYOMI KIZU、MASAKO KUNIMOTO、FUMIO YAMADA

  DOI：10.1248/cpb.33.3696

  日期：——

  Various 4-halogeno-3-indoleacetic acids and -3-indoleacetonitriles were synthesized for the first time by means of the Sandmeyer or Schiemann reaction, demonstrating the versatility of 4-indolediazonium salts in 4-substituted indole chemistry. A practical synthetic method for 4-halogenoindoles was developed by regio-selective thallation-halogenation, and the products were also led to 4-halogeno-3-indoleacetic acids. The first synthesis of 4-formyl-3-indoleacetonitrile is also reported.

  首次合成了多种4-卤代-3-吲哚乙酸和-3-吲哚乙腈，采用了桑德梅耶反应或施密特反应，展示了4-吲哚二氮盐在4-取代吲哚化学中的多样性。通过区域选择性的铊化-卤化开发了一种实用的4-卤代吲哚合成方法，所生成的产品也可转化为4-卤代-3-吲哚乙酸。此外，还报道了4-甲酰基-3-吲哚乙腈的首次合成。
• Rapid and efficient syntheses of tryptophans using a continuous-flow quaternization–substitution reaction of gramines with a chiral nucleophilic glycine equivalent
  作者：Daichi Koiwa、Masayuki Ohira、Takahiro Hiramatsu、Hidenori Abe、Tetsuji Kawamoto、Yuji Ishihara、Bernardo Ignacio、Noel Mansour、Todd Romoff

  DOI：10.1039/d2ob01682f

  日期：——

  continuous-flow quaternization reaction of gramines with MeI (<1 min) followed by a substitution reaction with a chiral nucleophilic glycine-derived Ni-complex (S)-2 (<1 min) has successfully been developed to afford the corresponding alkylated Ni-complexes 3 in good yields with excellent diastereoselectivity, based on the results of a one-pot quaternization–substitution reaction of gramines with (S)-2 in

  成功开发了禾本科植物与 MeI 的连续流动季铵化反应（<1 分钟），然后与手性亲核甘氨酸衍生的 Ni-络合物 ( S )- 2进行取代反应（<1 分钟），得到相应的烷基化 Ni - 基于禾本科化合物与 ( S )- 2在间歇过程中的一锅季铵化-取代反应的结果，以良好的产率和出色的非对映选择性配合物3。连续流动过程允许安全有效地放大合成3j（84% 产率，99% de，540 gh -1），得到 7-氮杂色氨酸衍生物 ( S )- 4j很容易通过酸催化的水解反应，然后用 Fmoc 基团保护。本方法以多种禾本科和( S ) -2为原料快速高效合成对映体纯非天然色氨酸衍生物，将有助于进一步促进多肽和蛋白质药物的发现和开发研究。
• Synthesis and bioactivity of psilocybin analogues containing a stable carbon–phosphorus bond
  作者：Marthe Vandevelde、Andreas Simoens、Bavo Vandekerckhove、Christian Stevens

  DOI：10.1039/d4md00043a

  日期：——

  Psilocybin analogues have been synthesized comprising a non-hydrolysable P–C bond to evaluate the biological activity and the selectivity towards 5-HT2AR, 5-HT2BR and the TNAP receptor. No activity was observed towards the phosphatase, however all compounds showed good binding affinity for 5-HT2AR and 5-HT2BR and one compound showed a higher selectivity towards 5-HT2AR than psilocin.

  已合成包含不可水解 P-C 键的裸盖菇素类似物，以评估其生物活性以及对 5-HT 2A R、5-HT 2B R 和 TNAP 受体的选择性。没有观察到对磷酸酶的活性，但是所有化合物都对 5-HT 2A R 和 5-HT 2B R 表现出良好的结合亲和力，并且一种化合物对 5-HT 2A R 表现出比赛洛辛更高的选择性。
• Cu-Mediated Oxidative Dimerization of Skatole to Tryptanthrin, an Indolo[2,1-b]quinazolone Alkaloid
  作者：Minoru Ishikura、Tomoki Itoh、Takumi Abe、Shuhei Nakamura

  DOI：10.3987/com-15-13228

  日期：——

  A one-pot conversion of skatole to tryptanthrin, an indolo[2,1-b]quinazoline alkaloid, was achieved by Cu-mediated oxidation.
• Discovery of 7-[¹⁸F]Fluorotryptophan as a Novel Positron Emission Tomography (PET) Probe for the Visualization of Tryptophan Metabolism in Vivo
  作者：Boris D. Zlatopolskiy、Johannes Zischler、Dominique Schäfer、Elizaveta A. Urusova、Mehrab Guliyev、Olesia Bannykh、Heike Endepols、Bernd Neumaier

  DOI：10.1021/acs.jmedchem.7b01245

  日期：2018.1.11

  Tryptophan and its metabolites are involved in different physiological and pathophysiological processes. Consequently, positron emission tomography (PET) tracers addressing tryptophan metabolic pathways should allow the detection of different pathologies like neurological disorders and cancer. Herein we report an efficient method for the preparation of fluorotryptophans labeled in different positions with F-18 and their biological evaluation. 4-7-[F-18]Fluorotryptophans ([F-18]FTrps) were prepared according to a modified protocol of alcohol-enhanced Cu-mediated radiofluorination in 30-53% radiochemical yields. In vitro experiments demonstrated high cellular uptake of 4-7[F-18]FTrps in different tumor cell lines. 4, 5-, and 6-[F-18]FTrps, although stable in vitro, suffered from rapid in vivo defluorination. In contrast, 7-[F-18]FTrp demonstrated a high in vivo stability and enabled a clear delineation of serotonergic areas and melatonin-producing pineal gland in rat brains. Moreover 7-[F-18]FTrp accumulated in different tumor xenografts in a chick embryo CAM model. Thus, 7-[F-18]FTrp represents a highly promising PET probe for imaging of Trp metabolism.