2-Methoxyxanthydrol | 152810-86-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-Methoxyxanthydrol
• 英文别名: 2-methoxy-9H-xanthen-9-ol；2-Methoxy xanthydrol
• CAS: 152810-86-1
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: ASWNSMIZJSJKOO-UHFFFAOYSA-N

物化性质

• 沸点：
  377.6±42.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Methoxyxanthydrol 在 三乙基硅烷 作用下， 以 二氯甲烷 、 三氟乙酸 为溶剂， 反应 0.5h， 以92%的产率得到2-methoxy-9H-xanthene
  参考文献：
  名称：

  Novel S-Xanthenyl Protecting Groups for Cysteine and Their Applications for the N^α-9-Fluorenylmethyloxycarbonyl (Fmoc) Strategy of Peptide Synthesis^1-3

  摘要：

  The 9H-xanthen-9-yl (Xan) and 2-methoxy-9H-xanthen-9-yl (2-Moxan) groups can be introduced onto sulfhydryl functions by S-alkylation reactions involving the corresponding xanthydrols, plus trifluoroacetic acid (TFA) as catalyst. Conversely, these groups are removed rapidly by acid in the presence of appropriate silane or thiol scavengers. The 3-methoxy-9H-xanthen-9-yl (3-Moxan) derivative was also studied, but abandoned for several reasons including challenging synthesis, excessive lability to acid, and insufficient stability in the presence of base. The N-alpha-9-fluorenyl-methyloxycarbonyl (Fmoc), S-Xan or 2-Moxan-protected cysteine derivatives were prepared and applied to the solid-phase syntheses of several model peptides. Selective removal of S-Xan and S-2-Moxan groups, while retaining tris(alkoxybenzyl)amide (PAL) anchoring, is best accomplished with TFA-CH2Cl2-Et3SiH (1:98.5:0.5), 25 degrees C, 2 h. Alternatively, oxidative deprotection of S-Xan or S-2-Moxan with iodine (10-20 equiv) or thallium(III) tris(trifluoroacetate) [Tl(tfa)(3)] (1-3 equiv) to provide disulfides can be carried out on peptide substrates both in solution and while polymer-bound. Compared to established chemistries with the acid-labile and oxidizable S-triphenylmethyl (Trt) group, S-Xan and S-2-Moxan gave equal or superior results in terms of peptide purities (including no detectable tryptophan alkylation) and overall yields.

  DOI：

  10.1021/jo961882g
• 作为产物：
  描述：

  2-氯苯甲酸 在 copper(I) oxide 、 硫酸 、 sodium methylate 、 sodium 、 乙酸酐 、 汞 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 2-Methoxyxanthydrol
  参考文献：
  名称：

  一些新型2-氯乙基亚硝基脲的合成及抗肿瘤活性

  摘要：

  一系列N-(2-氯乙基)-N'-(9H-xanthen-9-基)-N-亚硝基脲和N-(2-氯乙基)-N'-(9H-噻吨-9-基)的合成) -N - 亚硝基脲类。标题化合物在体外针对 NSCLCN6 L16 支气管表皮样癌进行了评估，发现其中一些具有活性。N-(2-氯乙基)-N'-(2-甲氧基-9H-黄原酸-9-基)-N-亚硝基脲(8e)对小鼠白血病P388肿瘤系统有活性。

  DOI：

  10.1002/ardp.19933260805

文献信息

• Iodine-catalyzed efficient synthesis of xanthene/thioxanthene-indole derivatives under mild conditions
  作者：Weihang Miao、Pingting Ye、Mengjiao Bai、Zhixin Yang、Suyue Duan、Hengpan Duan、Xuequan Wang

  DOI：10.1039/d0ra05217e

  日期：——

  xanthen-9-ol and thioxanthen-9-ol with indoles has been developed, providing an efficient procedure for the synthesis of xanthene/thioxanthene-indole derivatives with good to excellent yields. This protocol offers several advantages, such as short reaction times, green solvent, operational simplicity, easily available catalyst and mild reaction conditions. Moreover, this method showed good tolerance of functional

  开发了一种碘催化的呫吨-9-醇和噻吨-9-醇与吲哚的亲核取代反应，为合成呫吨/噻吨-吲哚衍生物提供了一种有效的方法，且收率良好。该方案具有反应时间短、溶剂绿色、操作简单、催化剂易得和反应条件温和等优点。此外，该方法对官能团和多种底物表现出良好的耐受性。
• Gastric antisecretory agents. 2. Antisecretory activity of 9-[(aminoalkyl)thio]-9H-xanthenes and 5-[(aminoalkyl)thio]-5H-[1]benzopyrano[2,3-b]pyridines
  作者：James A. Bristol、Elijah H. Gold、Irwin Gross、Raymond G. Lovey、James F. Long

  DOI：10.1021/jm00140a020

  日期：1981.8

  A series of 9-[(aminoalkyl)thio]-9H-xanthenes (3-6) and 5-[(aminoalkyl)thio]-5H-[1]benzopyrano[2,3-b]pyridines (7-10) possessing gastric antisecretory activity in the rat and dog is described Many of the compounds possessed good activity in the pylorus-ligated rat and several inhibited histamine-stimulated gastric acid secretion in the dog. The mechanism of acid secretion inhibition is not related

  一系列9-[（（氨基烷基）硫基] -9H-黄嘌呤（3-6）和5-[（（氨基烷基）硫基] -5H- [1]苯并吡喃并[2,3-b]吡啶（7-10）具有描述了在大鼠和狗中的胃抗分泌活性许多化合物在幽门结扎的大鼠中具有良好的活性，并且在狗中抑制了组胺刺激的胃酸分泌。抑制酸分泌的机制与抗胆碱能或组胺（H2）受体拮抗作用无关。
• BRISTOL, J. A.;GOLD, E. H.;GROSS, I.;LOVEY, R. G.;LONG, J. F., J. MED. CHEM., 1981, 24, N 8, 1010-1013
  作者：BRISTOL, J. A.、GOLD, E. H.、GROSS, I.、LOVEY, R. G.、LONG, J. F.

  DOI：——

  日期：——
• US3961069A
  申请人：——

  公开号：US3961069A

  公开（公告）日：1976-06-01
• Novel <i>S</i>-Xanthenyl Protecting Groups for Cysteine and Their Applications for the <i>N</i>^α-9-Fluorenylmethyloxycarbonyl (Fmoc) Strategy of Peptide Synthesis^1-3
  作者：Yongxin Han、George Barany

  DOI：10.1021/jo961882g

  日期：1997.6.13

  The 9H-xanthen-9-yl (Xan) and 2-methoxy-9H-xanthen-9-yl (2-Moxan) groups can be introduced onto sulfhydryl functions by S-alkylation reactions involving the corresponding xanthydrols, plus trifluoroacetic acid (TFA) as catalyst. Conversely, these groups are removed rapidly by acid in the presence of appropriate silane or thiol scavengers. The 3-methoxy-9H-xanthen-9-yl (3-Moxan) derivative was also studied, but abandoned for several reasons including challenging synthesis, excessive lability to acid, and insufficient stability in the presence of base. The N-alpha-9-fluorenyl-methyloxycarbonyl (Fmoc), S-Xan or 2-Moxan-protected cysteine derivatives were prepared and applied to the solid-phase syntheses of several model peptides. Selective removal of S-Xan and S-2-Moxan groups, while retaining tris(alkoxybenzyl)amide (PAL) anchoring, is best accomplished with TFA-CH2Cl2-Et3SiH (1:98.5:0.5), 25 degrees C, 2 h. Alternatively, oxidative deprotection of S-Xan or S-2-Moxan with iodine (10-20 equiv) or thallium(III) tris(trifluoroacetate) [Tl(tfa)(3)] (1-3 equiv) to provide disulfides can be carried out on peptide substrates both in solution and while polymer-bound. Compared to established chemistries with the acid-labile and oxidizable S-triphenylmethyl (Trt) group, S-Xan and S-2-Moxan gave equal or superior results in terms of peptide purities (including no detectable tryptophan alkylation) and overall yields.