2-C-(1-methoxyindol-3-yl)-β-L-xylo-3-hexulofuranosonic acid γ-lactone | 331754-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 2-C-(1-methoxyindol-3-yl)-β-L-xylo-3-hexulofuranosonic acid γ-lactone
• 英文别名: 2-C-[(1-methoxyindol-3-yl)methyl]-α-L-xylo-hex-3-uloforanoso-1,4-lactone；2-C-(1-methoxy-3-indolylmethyl)-α-L-xylo-3-hexulofuranosono-1,4-lactone；1-methoxyascorbigen；N-Methoxyascorbigen；Neoascorbigen；(3S,3aR,6S,6aS)-3,6,6a-trihydroxy-6-[(1-methoxyindol-3-yl)methyl]-3,3a-dihydro-2H-furo[3,2-b]furan-5-one
• CAS: 331754-99-5
• 化学式: C₁₆H₁₇NO₇
• 分子量: 335.313
• InChiKey: RZRVFWGHJJZBJQ-XNISGKROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-C-(1-methoxyindol-3-yl)-β-L-xylo-3-hexulofuranosonic acid γ-lactone 在 维生素 C 作用下， 以 水 为溶剂， 反应 48.0h， 以27%的产率得到2-hydroxy-4-hydroxymethyl-3-(1-methoxylindol-3-yl)-cyclopent-2-enone
  参考文献：
  名称：

  The formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)cyclopent-2-enone derivatives from ascorbigens

  摘要：

  A facile preparation is described of 3-(indol-3-yl)-2-hydroxy-4-hydroxymethylcyclopent-2-enone and its N-derivatives in 15-40% yields by the degradation of ascorbigen or its N-derivatives in a warm solution of L-ascorbic acid through a sequential domino reaction. The same cyclopentenone derivatives were obtained in 30-40% yields by the condensation of (N-alkylindol-3-yl)glycolic acids with ascorbic acid. 2,6-Dihydroxy-1-(indol-3-yl)hexa-1,4-diene-3-one and 2-hydroxy-4-hydroxymethyl-5-(indol-3-yl)cyclopent-2-enone were identified as intermediates in this reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00310-4
• 作为产物：
  描述：

  1-甲氧基-1H-吲哚-3-甲醛 在 sodium tetrahydroborate 、 citrate-phosphate buffer 作用下， 以 乙醇 为溶剂， 反应 16.17h， 生成 2-C-(1-methoxyindol-3-yl)-β-L-xylo-3-hexulofuranosonic acid γ-lactone
  参考文献：
  名称：

  Investigation of neoascorbigen

  摘要：

  DOI：

  10.1007/bf02283542

文献信息

• Study of 1-deoxy-1-(indol-3-yl)-l-sorbose, 1-deoxy-1-(indol-3-yl)-l-tagatose, and their analogs
  作者：Sergey N Lavrenov、Alexander M Korolev、Marina I Reznikova、Andrey V Sosnov、Maria N Preobrazhenskaya

  DOI：10.1016/s0008-6215(02)00404-4

  日期：2003.1

  Alkaline degradation of the ascorbigen 2-C-[(indol-3-yl)methyl]-alpha-L-xylo-hex-3-ulofuranosono-1,4-lactone (1a) led to a mixture of 1-deoxy-1-(indol-3-yl)-L-sorbose (2a) and 1-deoxy-1-(indol-3-yl)-L-tagatose (3a). The mixture of diastereomeric ketoses underwent acetylation and pyranose ring opening under the action of acetic anhydride in pyridine in the presence of 4-dimethylaminopyridine (DMAP)

  抗坏血酸2-C-[（（吲哚-3-基）甲基]-α-L-二甲苯基-hex-3-ulofuranosono-1,4-内酯（1a）的碱性降解导致1-deoxy-1的混合物-（吲哚-3-基）-L-山梨糖（2a）和1-脱氧-1-（吲哚-3-基）-L-塔格糖（3a）。非对映体酮糖的混合物在4-二甲基氨基吡啶（DMAP）存在下，在乙酸酐的吡啶中，在乙酸酐的作用下进行乙酰化和吡喃糖开环，形成（E）-2,3,4,5,6-混合物五-O-乙酰基-1-脱氧-1-（吲哚-3-基）-L-木基-己基-1-烯醇（4a）和（E）-2,3,4,5,6-penta-O -乙酰基-1-脱氧-1-（吲哚-3-基）-L-lyxo-己基-1-烯醇（5a），将其色谱分离。4a或5a脱乙酰基提供环化的四醇，将其甲苯磺酸化混合可生成1-deoxy-1-（吲哚-3-yl）-3,5-di-O-甲苯磺酰基-α-L-山梨糖醛糖（12a）和1 -脱氧-
• Synthesis and study of neoscorbigen and its analogs
  作者：V. I. Mukhanov、M. M. Kaganskii、A. A. Sorokin、S. G. Antonyan、G. V. Tananova、L. L. Mikhailevskaya、A. S. Kinzirskii、M. N. Preobrazhenskaya

  DOI：10.1007/bf02219244

  日期：1994.7
• From ascorbigens to indolocarbazoles
  作者：Maria N. Preobrazhenskaya、Alexander M. Korolev、Ilya I. Rozhkov、Larisa N. Yudina、Eduard I. Lazhko、Enrico Aiello、Anna Maria Almerico、Francesco Mingoia

  DOI：10.1016/s0014-827x(99)00026-9

  日期：1999.5

  New methods of L-ascorbic acid derivatization with the use of polyfunctional indole-3-cabinols are described. Reaction of beta-hydroxy-N-methyltryptamine and L-ascorbic acid gave lactame derivatives; (indol-3-yl)glycolic and L-ascorbic acids produced 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl) Similarly, 4-hydroxy-3-methoxyphenylglycolic and L-ascorbic acids yielded 2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-4-hydroxymethyl-cyclopen-2-enone. Properties of N-methoxyascorbigen (neoascorbigen) were investigated. Alkylation of L-ascorbic acid with polysubstituted pyrrolecarbinols led to pyrrole analogues of ascorbigen. Acidic transformation of 3-formylindole and 1-methyl-3-formylindole led to indolocarbazoles and triindolyhmethane derivatives. (C) 1999 Elsevier Science S.A. All rights reserved.
• The formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)cyclopent-2-enone derivatives from ascorbigens
  作者：Alexander M Korolev、Larisa N Yudina、Ilyia I Rozhkov、Ludmila N Lysenkova、Eduard I Lazhko、Yury N Luzikov、Maria N Preobrazhenskaya

  DOI：10.1016/s0008-6215(00)00310-4

  日期：2001.2

  A facile preparation is described of 3-(indol-3-yl)-2-hydroxy-4-hydroxymethylcyclopent-2-enone and its N-derivatives in 15-40% yields by the degradation of ascorbigen or its N-derivatives in a warm solution of L-ascorbic acid through a sequential domino reaction. The same cyclopentenone derivatives were obtained in 30-40% yields by the condensation of (N-alkylindol-3-yl)glycolic acids with ascorbic acid. 2,6-Dihydroxy-1-(indol-3-yl)hexa-1,4-diene-3-one and 2-hydroxy-4-hydroxymethyl-5-(indol-3-yl)cyclopent-2-enone were identified as intermediates in this reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Investigation of neoascorbigen
  作者：L. N. Yudina、A. M. Korolev、M. I. Reznikova、M. N. Preobrazhenskaya

  DOI：10.1007/bf02283542

  日期：2000.2