Nb-acetyl-2,3-dihydrotryptamine | 79426-44-1

• 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: Nb-acetyl-2,3-dihydrotryptamine
• 英文别名: N-[2-(2,3-dihydro-1H-indol-3-yl)ethyl]acetamide
• CAS: 79426-44-1
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: LGWUGAXPKZWKCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Nb-acetyl-2,3-dihydrotryptamine 在 sodium tungstate 、 三氟化硼 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 褪黑素
  参考文献：
  名称：

  The Ideal Synthetic Method Aimed at the Leads for an a2-Blocker, an Inhibitor of Blood Platelet Aggregation, and an Anti-osteoporosis Agent

  摘要：

  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.

  DOI：

  10.3987/com-06-10771
• 作为产物：
  描述：

  methyl 2-(1-H-indol-3-yl)ethylcarbamate 在 三乙基硅烷 、 三乙胺 作用下， 以 三氟乙酸 为溶剂， 生成 Nb-acetyl-2,3-dihydrotryptamine
  参考文献：
  名称：

  The Ideal Synthetic Method Aimed at the Leads for an a2-Blocker, an Inhibitor of Blood Platelet Aggregation, and an Anti-osteoporosis Agent

  摘要：

  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.

  DOI：

  10.3987/com-06-10771

文献信息

• Approaches to the Synthesis of (±)-Strychnine via the Cobalt-Mediated [2 + 2 + 2] Cycloaddition:  Rapid Assembly of a Classic Framework
  作者：Michael J. Eichberg、Rosa L. Dorta、Douglas B. Grotjahn、Kai Lamottke、Martin Schmidt、K. Peter C. Vollhardt

  DOI：10.1021/ja016333t

  日期：2001.9.1

  Five synthetic approaches to racemic strychnine (1), with the cobalt-mediated [2 + 2 + 2] cycloaddition of alkynes to indoles as the key step, are described. These include the generation and attempted cyclization of macrocycle 8 and the synthesis of dihydrocarbazoles 15, 22, and 26 and their elaboration to pentacyclic structures via a conjugate addition, dipolar cycloaddition, and propellane-to-spirofused

  描述了外消旋士的宁 (1) 的五种合成方法，其中钴介导的炔烃与吲哚的 [2 + 2 + 2] 环加成反应是关键步骤。这些包括大环 8 的生成和尝试环化以及二氢咔唑 15、22 和 26 的合成，以及它们分别通过共轭加成、偶极环加成和推进烷到螺旋融合骨架重排形成五环结构。最后讨论了1的成功全合成。烯炔基吲哚 40 与乙炔的环化和胺 49 的正式分子内 1,8-共轭加成形成五环 50，突出了短而高度收敛的路线（最长线性序列中的 14 个步骤）的发展。
• The chemistry of indoles. Part 57. The chemistry of 1-hydroxyindoles: Syntheses of methyl 1-hydroxyindole-3-acetate, Nb-acetyl-1-hydroxytryptamine, (-)- and (S)-1-hydroxytryptophan derivatives.
  作者：Masanori SOMEI、Toshiya KAWASAKI、Kazuhisa SHIMIZU、Yoshikazu FUKUI、Toshiharu OHTA

  DOI：10.1248/cpb.39.1905

  日期：——

  Methyl 1-hydroxyindole-3-acetate, (±)-2-acetoamino-3-(10hydroxyindol-3-yl)propanol, N__-b-acetyl-1-hydroxytryptamine, (±)- and (S__-)-(+)-N__-b-acetyl-1-hydroxytryptophan methyl ester, which are needed for inspecting our hypothesis regarding the metabolism of tryptophan, were prepared for the first time. The structural proof of (±)-N__-b-acetyl-1-hydroxytryptophan methyl ester by X-ray crysatllographic analysis is also reported.

  首次制备了 1-羟基吲哚-3-乙酸甲酯、(±)-2-乙酰氨基-3-(10-羟基吲哚-3-基)丙醇、N__-b-乙酰基-1-羟基色胺、(±)-和(S__-)-(+)-N__-b-乙酰基-1-羟基色氨酸甲酯。报告还通过 X 射线晶体分析法证明了 (±)-N__-b-acetyl-1-hydroxytryptophan methyl ester（(±)-N__-b-乙酰基-1-羟基色氨酸甲酯）的结构。
• NEGATIVE PHOTOCHROMIC MATERIALS WITH TUNABLE PROPERTIES
  申请人：The Regents of the University of California

  公开号：US20190127345A1

  公开（公告）日：2019-05-02

  Embodiments of the present disclosure describe a negative photochromatic material. Embodiments of the present disclosure further describe a method of tuning a negative photochromatic material comprising selecting an amine donor group, selecting an acceptor group, and contacting at least the selected amine donor group and the selected acceptor group to form a negative photochromatic material, wherein one or more of the selected amine donor group and the selected acceptor group tune at least an absorption range of the negative photochromatic material.

  本公开的实施例描述了一种负光致变色材料。本公开的实施例进一步描述了一种调节负光致变色材料的方法，包括选择胺供体基团，选择受体基团，并将至少选择的胺供体基团和选择的受体基团接触以形成负光致变色材料，其中至少选择的胺供体基团和选择的受体基团中的一个或多个调节负光致变色材料的吸收范围。
• Palladium-Catalyzed Asymmetric Hydrogenation of Unprotected 3-Substituted Indoles
  作者：Kun Wang、Yan-Jiang Yu、Xiao-Qing Wang、Yu-Qing Bai、Mu-Wang Chen、Yong-Gui Zhou

  DOI：10.1021/acs.joc.2c00702

  日期：2022.8.5

  A palladium-catalyzed asymmetric hydrogenation of unprotected 3-substituted indoles was developed, providing a series of 3-substituted indolines in excellent yields with ≤94.4:5.6 er. The large sterically hindered bisphosphine ligand played a crucial role in the enantioselective control. In addition, the gram-scale hydrogenation experiment and product derivatizations were performed successfully.

  开发了一种钯催化的未保护的 3-取代吲哚的不对称氢化，以 ≤94.4:5.6 er 的优异收率提供了一系列 3-取代二氢吲哚。大的空间位阻双膦配体在对映选择性控制中起着至关重要的作用。此外，成功地进行了克级加氢实验和产品衍生化。
• Syntheses of Melatonin and Its Derivatives
  作者：Masanori Somei、Yoshikazu Fukui、Masakazu Hasegawa、Naoki Oshikiri、Toshikatsu Hayashi

  DOI：10.3987/com-00-8930

  日期：——

  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.