(+/-)-Nb-acetyl-1-hydroxytryptophan methyl ester | 136788-91-5

• 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-hydroxytryptophan methyl ester
• 英文别名: Methyl 2-acetamido-3-(1-hydroxyindol-3-yl)propanoate
• CAS: 136788-91-5
• 化学式: C₁₄H₁₆N₂O₄
• 分子量: 276.292
• InChiKey: DJIUHBSTGGIECQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-Nb-acetyl-1-hydroxytryptophan methyl ester 在 氯化亚砜 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-Acetylamino-3-(1-acetyl-5-chloro-1H-indol-3-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Nucleophilic Substitution Reaction of 1-Hydroxytryptophan and 1-Hydroxytryptamine Derivatives (Regioselective Syntheses of 5-Substituted Derivatives of Tryptophane and Tryptamine)

  摘要：

  Regioselective nucleophilic substitution at the 5-position of indole nucleus was observed in the reaction of 1-hydroxytryptophan and 1-hydroxytryptamine derivatives with acids, suggesting the mechanism of serotonin formation in the central nervous system.

  DOI：

  10.3987/com-93-6391
• 作为产物：
  描述：

  (+/-)-Nb-acetyl-2,3-dihydrotryptophan methyl ester 在 sodium tungstate 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 以73%的产率得到(+/-)-Nb-acetyl-1-hydroxytryptophan methyl ester
  参考文献：
  名称：

  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.

  摘要：

  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。

  DOI：

  10.1248/cpb.39.1905

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 1-Hydroxyindole Derivatives: Nucleophilic Substitution Reactions on Indole Nucleus
  作者：Masanori Somei、Toshiya Kawasaki、Yoshikazu Fukui、Fumio Yamada、Tetsuya Kobayashi、Harumi Aoyama、Daisuke Shinmyo

  DOI：10.3987/com-92-6140

  日期：——

  Nucleophilic substitution reactions were newly found to occur generally in the chemistry of 1-hydroxyindole derivatives. Its application to the synthesis of a phytoalexin, brassicanal A, is reported.
• 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.
• Yamada, Fumio; Goto, Aya; Peng, Wu, Heterocycles, 2003, vol. 61, p. 163 - 172
  作者：Yamada, Fumio、Goto, Aya、Peng, Wu、Hayashi, Toshikatsu、Saga, Yoshitomo、Somei, Masanori

  DOI：——

  日期：——
• A [3,3] Sigmatropic and Novel Ipso [3,3] Sigmatropic Rearrangement of 1-Hydroxyindole Chemistry
  作者：Masanori Somei、Yoshikazu Fukui、Tetsuya Kobayashi、Toshiya Kawasaki、Fumio Yamada

  DOI：10.3987/com-18-s(f)42

  日期：——