Nb-acetyl-1-hydroxytryptamine | 136788-90-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Nb-acetyl-1-hydroxytryptamine
• 英文别名: N-[2-(1-hydroxyindol-3-yl)ethyl]acetamide
• CAS: 136788-90-4
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: BZVCNWIQUMTGDZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Nb-acetyl-1-hydroxytryptamine 在 三乙基硅烷 、 sodium tungstate 、 双氧水 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 1-hydroxymelatonin
  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：

  methyl 2-(1-H-indol-3-yl)ethylcarbamate 在 三乙基硅烷 、 sodium tungstate 、 双氧水 、 三乙胺 作用下， 以 甲醇 、 水 、 三氟乙酸 为溶剂， 反应 2.0h， 生成 Nb-acetyl-1-hydroxytryptamine
  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

• Nucleophilic Substitution Reactions on Indole Nucleus: Formation of (3a,8a-cis)-1,2,3,3a,8,8a-Hexahydropyrrolo[2,3-b]indoles Having a Substituent at the 3a-Position
  作者：Masanori Somei、Fumio Yamada、Aya Goto、Masakazu Hasegawa、Kensuke Kobayashi

  DOI：10.3987/com-16-s(s)53

  日期：——

  ictly determined. INTRODUCTION We have opened the door to the chemistry of 1-hydro xyindole and 1-hydroxytryptophan derivatives, 3 and demonstrated that these compounds generally undergo nucleophilic substitution reaction, 4 which was thus far rarely observed in indole chemistry. 4 In our 1-hydroxyindole hypothesis, 5 we assume the 1-hydroxy group of the general formu la (A) in Scheme 1 departs, after

  各种亲核试剂，如吲哚、1,2,3-三乙氧基苯、苯甲醚、苯酚和吡咯，在甲磺酰氯存在下与1-羟基-Nb-三氟乙酰色胺反应生成新的(3a,8acis)系列-1,2,3,3a,8,8a-六氢吡咯并[2,3b]吲哚在3a位有一个取代基。它们的结构和副产品是严格确定的。引言 我们打开了 1-羟基吲哚和 1-羟基色氨酸衍生物 3 化学的大门，并证明这些化合物通常会发生亲核取代反应 4，这在吲哚化学中迄今为止很少观察到。4 在我们的 1-羟基吲哚假设中，5 我们假设方案 1 中通式 (A) 的 1-羟基基团在转化为良好的离去基团 (B) 后离开，留下共振稳定的吲哚基阳离子 (C) . 可以用合适的亲核试剂捕获它，得到亚胺 6 (D)。# 献给 M asakatsu Shibasaki NHR 教授 70 岁生日
• 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。
• Somei, Masanori; Yamada, Fumio; Morikawa, Harunobu, Heterocycles, 1997, vol. 46, p. 91 - 94
  作者：Somei, Masanori、Yamada, Fumio、Morikawa, Harunobu

  DOI：——

  日期：——
• Hasegawa, Masakazu; Tabata, Mutsuko; Satoh, Keiichi, Heterocycles, 1996, vol. 43, # 11, p. 2333 - 2342
  作者：Hasegawa, Masakazu、Tabata, Mutsuko、Satoh, Keiichi、Yamada, Fumio、Somei, Masanori

  DOI：——

  日期：——
• Reactions of 1-Hydroxyindoles with p-Toluenesulfonyl Chloride and p-Toluenesulfonic Acid
  作者：Masanori Somei、Fumio Yamada、Aya Goto、Masumi Hayashi、Masakazu Hasegawa

  DOI：10.3987/com-00-9038

  日期：——

  1-Hydroxyindoles produced novel types of compounds such as 4-substituted indoles and 4H-1, 3-dioxolo[4,5-b]indoles upon reaction with p-toluenesulfonyl chloride in acetone. Contrastively, 5-tosyloxyindole and 2H-1,2-oxazino[2, 3-a]indole were generated upon reaction with p-toluenesulfonic acid in acetone.