2-hydroxymethyl-2,3-dihydro-4H-1,4-benzodioxine methanesulfonate | 7031-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2-hydroxymethyl-2,3-dihydro-4H-1,4-benzodioxine methanesulfonate
• 英文别名: (+/-)-1,4-benzodioxan-2-ylmethyl mesylate；(+/-)-2-mesyloxymethyl-1,4-benzodioxane；2-mesyloxymethyl-1,4-benzodioxane；2,3-dihydro-1,4-benzodioxin-2-methanol methanesulfonate；2-methanesulfonyloxymethyl-2,3-dihydro-benzo[1,4]dioxine；2,3-dihydro-1,4-benzodioxin-2-methanol methanesulfonate (ester)；2,3-Dihydro-1,4-benzodioxin-2-ylmethyl methanesulfonate；2,3-dihydro-1,4-benzodioxin-3-ylmethyl methanesulfonate
• CAS: 7031-65-4
• 化学式: C₁₀H₁₂O₅S
• 分子量: 244.268
• InChiKey: DKZOUTWWMFKQGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxymethyl-2,3-dihydro-4H-1,4-benzodioxine methanesulfonate 在 sodium phosphate dodecahydrate 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 methyl 4-((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methoxy)-2-(thiophen-2-yl)benzoate
  参考文献：
  名称：

  Farnesyltransferase inhibitors: CAAX mimetics based on different biaryl scaffolds

  摘要：

  Mimetics of the C-terminal CAAX tetrapeptide of Ras protein were designed as farnesyltransferase (FTase) inhibitors (FTIs) by replacing AA with o-aryl or o-heteroaryl substituted p-hydroxy- or p-aminobenzoic acid, while maintaining the replacement of C with 1,4-benzodioxan-2-ylmethyl or 2-amino-4-thiazoly-lacetyl residue as in previous CAAX mimetics. Both FTase inhibition and antiproliferative effect were showed by two thiazole derivatives, namely those with 1-naphthyl (10 and 10a) or 3-furanyl (15 and 15a) in the central spacer, and by the benzodioxane derivative with 2-thienyl (6 and 6a) in the same position. Accumulation of unprenylated RAS was demonstrated in cells incubated with 15a. Consistently with FTIs literature, such results delineate the biaryl scaffold not only as a spacer but also as a sensible area of these mimetic molecules, where modifications at the branching aromatic ring are not indifferent and should be matter of further investigation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.078
• 作为产物：
  描述：

  甲基磺酰氯 、 2-羟基甲基-1,4-苯二恶 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到2-hydroxymethyl-2,3-dihydro-4H-1,4-benzodioxine methanesulfonate
  参考文献：
  名称：

  A short entry to enantiopure 2-substituted 1,4-benzodioxanes by efficient resolution methods

  摘要：

  (R)-1,4-Benzodioxane-2-carboxilic acid (R)-1 was obtained by resolution of the racemic acid 1 with stoichiometric or nonstoichiometric (+)-dehydroabietylamine (+)-2 in high chemical yield and enantiomeric excess. (S)-1 was isolated from the mother liquors of the crystallisation of (R)-1-(+)-2 and its enantiomeric excess maximised by recrystallisation procedures involving a precipitation under kinetic control or, alternatively, by conversion into the methyl ester followed by a single crystallisation. The different mechanisms of the two S enrichments is well explained by the binary phase diagrams of the acid and of the ester, which show that the former is a racemic compound, whereas the latter a conglomerate. The DSC analyses were extended to 2-hydroxymethyl- and 2-mesyloxymethyl-1,4-benzodioxane, establishing that the alcohol forms a racemic compound, while its mesyl ester a conglomerate. On the basis of these results, different resolution strategies can be designed to obtain useful homochiral 2-substituted 1,4-benzodioxanes coupling the resolution of I via diastereomeric salt formation with the enantiomeric enrichments by recrystallisations, preferably of its conglomerate forming derivatives. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.09.012

文献信息

• 1-(arylthioalkyl, arylaminoalkyl or arylmethylenealkyl)-4-(heteroaryl)
  申请人：Hoechst Roussel Pharmaceuticals, Inc.

  公开号：US05605913A1

  公开（公告）日：1997-02-25

  Heteroarylpiperidines, pyrrolidines, and piperazines are useful as antipsychotic and analgesic agents. the compounds are especially useful for treating psychoses by administering to a mammal a psychoses-treating effective amount of one of the compounds. Depot derivatives of the compounds are useful for providing long acting effects of the compounds. The compounds are also useful as analgesics by administering a pain-relieving effective amount of one of the compounds to a mammal.

  杂芳基哌啶、吡咯烷和哌嗪作为抗精神病和镇痛剂是有用的。这些化合物特别适用于通过向哺乳动物施用治疗精神病有效量的其中一种化合物来治疗精神病。这些化合物的长效衍生物对于提供这些化合物的长期作用是有用的。通过向哺乳动物施用镇痛有效量的其中一种化合物，这些化合物也作为镇痛剂有用。
• Heteroarylpiperidines, pyrrolidines and piperazines and their use as
  申请人：Hoechst-Roussel Pharmaceuticals, Inc.

  公开号：US05364866A1

  公开（公告）日：1994-11-15

  Heteroarylpiperidines, pyrrolidines, and piperazines are useful as antipsychotic and analgesic agents. The compounds are especially useful for treating psychoses by administering to a mammal a psychoses-treating effective amount of one of the compounds. The compounds are also useful as analgesics by administering a pain-relieving effective amount of one of the compounds to a mammal.

  吡啶基哌啶、吡咯烷和哌嗪等杂环哌啶类化合物可用作抗精神病和镇痛剂。这些化合物特别适用于通过向哺乳动物施用其中一种化合物的抗精神病有效量来治疗精神病。这些化合物也可通过向哺乳动物施用其中一种化合物的镇痛有效量来用作镇痛剂。
• Ether substituted benzodioxan derivatives
  申请人：Sandoz Ltd.

  公开号：US04036980A1

  公开（公告）日：1977-07-19

  Benzodioxan derivatives of formula, ##STR1## in which R is a group of formula A ##STR2## or of formula B, --(CH.sub.2).sub.p --CR.sub.6 =CR.sub.5 --(CH.sub.2).sub.n --O--R.sub.2 B wherein R.sub.2 is a hydrocarbon radical, e.g. alkyl or cycloalkyl, R.sub.3 and R.sub.4, independently, are hydrogen or alkyl, R.sub.5 and R.sub.6, independently, are hydrogen or methyl, m, n and p are integers, R.sub.1 is hydrogen or alkyl, X is oxygen or sulphur And Z is hydrogen or a substituent, e.g. alkyl, are useful as insect and acarid growth inhibiting agents.

  Benzodioxan衍生物的化学式如下：##STR1## 其中R是化学式A ##STR2## 或者化学式B的一个基团，--(CH.sub.2).sub.p --CR.sub.6 =CR.sub.5 --(CH.sub.2).sub.n --O--R.sub.2 B，其中R.sub.2是一个碳氢基团，例如烷基或环烷基，R.sub.3和R.sub.4独立地是氢或烷基，R.sub.5和R.sub.6独立地是氢或甲基，m、n和p是整数，R.sub.1是氢或烷基，X是氧或硫，Z是氢或取代基，例如烷基，这些化合物可用作昆虫和螨类生长抑制剂。
• Anti-hypertensive benzodioxan derivatives
  申请人：Bouchara; Emile

  公开号：US04432984A1

  公开（公告）日：1984-02-21

  This invention relates to benzodioxanylalkylpiperidines, to processes for producing them and to the pharmaceutical compositions containing such compounds as active ingredient. This invention also relates to a method for treating hypertension in hypertensive mammals.

  本发明涉及苯二氧杂基烷基哌啶类化合物，涉及生产这些化合物的方法以及含有这些化合物作为活性成分的药物组合物。本发明还涉及一种治疗高血压的方法，适用于高血压哺乳动物。
• New antihistaminic N-heterocyclic 4-piperidinamines. 3. Synthesis and antihistaminic activity of N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amines
  作者：Frans Janssens、Joseph Torremans、Marcel Janssen、Raymond A. Stokbroekx、Marcel Luyckx、Paul A. J. Janssen

  DOI：10.1021/jm00150a030

  日期：1985.12

  the bioisosteric replacement of a 2-pyridyl ring for a phenyl nucleus in astemizole, a series of N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amines was synthesized and evaluated. The title compounds were obtained starting from either 8a or 8b by four synthetic methods. The in vivo antihistamine activity was evaluated by the compound 48/80-induced lethality test in rats and the histamine-induced lethality

  为了研究阿司咪唑中苯基核的2-吡啶基环的生物立体取代，合成并评估了一系列N-（4-哌啶基）-3H-咪唑并[4,5-b]吡啶-2-胺。通过四种合成方法从8a或8b开始获得标题化合物。口服和/或皮下给药后，通过化合物48/80在大鼠中的致死性测试和豚鼠中组胺在致死性中的测试来评估体内抗组胺活性。化合物37（阿司咪唑的等排物）在大鼠中显示出最有效的抗组胺特性。但是，就作用持续时间和总效力而言，阿司咪唑优于37。