1-hydroxy-Nb-methoxycarbonyltryptamine | 180910-53-6

• 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: 1-hydroxy-Nb-methoxycarbonyltryptamine
• 英文别名: 1-hydroxy-N-methoxycarbonyltryptamine；Carbamic acid, [2-(1-hydroxy-1H-indol-3-yl)ethyl]-, methyl ester；methyl N-[2-(1-hydroxyindol-3-yl)ethyl]carbamate
• CAS: 180910-53-6
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: HOKKPWFYPCZZNA-UHFFFAOYSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-hydroxy-Nb-methoxycarbonyltryptamine 在 吡啶 、 sodium hydroxide 、 三氟化硼 作用下， 以 甲醇 为溶剂， 反应 5.34h， 生成 褪黑素
  参考文献：
  名称：

  Syntheses of Melatonin and Its Derivatives

  摘要：

  Two simple synthetic methods for melatonin are newly developed from tryptamine through intermediates, which are promising lead compounds for drug developing research. Novel chemical reactivities of melatonin in its bromination, lithiation, and acylation are also reported.

  DOI：

  10.3987/com-00-8930
• 作为产物：
  描述：

  色胺 在 三乙基硅烷 、 sodium tungstate 、 双氧水 、 三乙胺 作用下， 以 三氟乙酸 为溶剂， 反应 2.0h， 生成 1-hydroxy-Nb-methoxycarbonyltryptamine
  参考文献：
  名称：

  Somei, Masanori; Yamada, Fumio; Morikawa, Harunobu, Heterocycles, 1997, vol. 46, p. 91 - 94

  摘要：

  DOI：

文献信息

• Nucleophilic Substitution Reaction on the Nitrogen of Indole Nucleus: A Novel Synthesis of 1-Aryltryptamines
  作者：Masanori Somei、Toshikatsu Hayashi、Wu Peng、Yu-ya Nakai、Koji Yamada

  DOI：10.3987/com-01-9417

  日期：——

  1-Hydroxytryptamine derivatives undergo nucleophilic substitution reaction on the indole nitrogen (Na) as a general reaction by the treatment with acid, providing a novel synthetic method for 1-aryltryptamines. Depending on the structures of nucleophiles, 5- and 7-substituted tryptamines can also be produced in addition to the 1-aryltryptamines.

  1-羟基色胺衍生物通过酸处理作为一般反应在吲哚氮（Na）上发生亲核取代反应，为1-芳基色胺的合成提供了一种新方法。根据亲核试剂的结构，除了 1-芳基色胺之外，还可以产生 5-和 7-取代的色胺。
• The Chemistry of Indoles. CIII. Simple Syntheses of Serotonin, N-Methylserotonin, Bufotenine, 5-Methoxy-N-methyltryptamine, Bufobutanoic Acid, N-(Indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and Lespedamine Based on 1-Hydroxyindole Chemistry.
  作者：Masanori SOMEI、Fumio YAMADA、Takashi KURAUCHI、Yoshiyuki NAGAHAMA、Masakazu HASEGAWA、Koji YAMADA、Sakiko TERANISHI、Haruhiko SATO、Chikara KANEKO

  DOI：10.1248/cpb.49.87

  日期：——

  Application of regioselective nucleophilic substitution reactions of 1-hydroxytryptamines to novel and simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), 5-methoxy-N-methyltryptamine (2a), bufobutanoic acid (3a), N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine (4), and lespedamine (5) are described. Effective syntheses of 5-benzyloxytryptamine and 1-methoxy-2-oxindoles are also reported.

  本文描述了利用1-羟色胺的选择性亲核取代反应，合成新型简单物质的方法，这些物质包括：血清素（1a）、N-甲基血清素（1b）、蟾毒色胺（1c）、5-甲氧基-N-甲基色胺（2a）、蟾毒色酸（3a）、N-(吲哚-3-基)甲基-5-甲氧基-N-甲基色胺（4）和莱斯佩达明（5）。此外，还报道了有效的5-苄氧基色胺和1-甲氧基-2-氧吲哚合成方法。
• Mechanistic duality of indolyl 1,3-heteroatom transposition
  作者：Yujin Lee、Yun Seung Nam、Soo Young Kim、Jeong Eun Ki、Hong Geun Lee

  DOI：10.1039/d3sc00716b

  日期：——

  A novel mechanistic duality has been revealed from the indolyl 1,3-heteroatom transposition (IHT) of N-hydroxyindole derivatives. A series of in-depth mechanistic investigations suggests that two separate mechanisms are operating simultaneously. Moreover, the relative contribution of each mechanistic pathway, the energy barrier for each pathway, and the identity of the primary pathway were shown to

  N-羟基吲哚衍生物的吲哚基1,3-杂原子转位（ IHT）揭示了一种新的机制二元性。一系列深入的机制研究表明，两个独立的机制同时运作。此外，每个机械途径的相对贡献、每个途径的能量势垒以及主要途径的特性都被证明是基底系统的电子特性的函数。基于所获得的机理理解，开发了一种在吲哚 3 位上通用且有效地引入杂原子的机制驱动策略。所开发的反应具有广泛的底物范围，可提供各种形式的官能化吲哚产物。此外，该方法适用于氧基和氮基官能团的引入。
• Simple Synthetic Method for 1,2,3,3a,8,8a-Hehahydropyrrolo[2,3-b]indoles Having a Halogen or an Oxygen Functional Group at the 3a-Position
  作者：Masanori Somei、Takako Iwaki、Yoshikazu Fukui、Masaki Okigawa、Fumio Yamada、Yoshiyuki Nagahama、Sachiko Ogasawara、Satomi Tanaka、Shiho Funaki

  DOI：10.3987/com-15-s(t)40

  日期：——

  1-Methoxy-Nb-methoxycarbonyltryptamine derivatives are successfully converted by either halogenating reagents or iodine/morpholine to 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indoles having a halogen or an oxygen functional group at the 3a-position. Synthesis of the corresponding methyl 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylates is also reported.
• The Ideal Synthetic Method Aimed at the Leads for an a2-Blocker, an Inhibitor of Blood Platelet Aggregation, and an Anti-osteoporosis Agent
  作者：Masanori Somei、Takako Iwaki、Fumio Yamada、Yoshio Tanaka、Koki Shigenobu、Katsuo Koike、Nobuo Suzuki、Atsuhiko Hattori

  DOI：10.3987/com-06-10771

  日期：——

  According to the definition of the ideal synthetic method, an example aimed at the leads for an alpha(2)-blocker, an inhibitor of platelet aggregation, and an anti-osteoporosis agent is established starting from tryptamine. The originality rate, the intellectual property, and the application potential factors of the method are 71, 54, and 100, respectively. The method employs only conventional reagents and reaction conditions without using any protecting groups.