Pyridoxin-formaldehydacetal | 1622-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Pyridoxin-formaldehydacetal
• 英文别名: 8-Methyl-1,5-dihydro-[1,3]dioxepino[5,6-c]pyridin-9-ol
• CAS: 1622-73-7
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: YJSRGCIKKTVSAW-UHFFFAOYSA-N

物化性质

• 熔点：
  175-176 °C
• 沸点：
  392.6±42.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  51.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Pyridoxin-formaldehydacetal 、 对氨基苯磺酸 在 盐酸 、 sodium nitrite 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  吡哆醇基己二唑衍生物及其偶氮类似物的合成和非线性光学性质

  摘要：

  摘要 合成了一系列新的噻菌灵衍生物及其在吡哆醇环的第 6 位带有苯基烯基和苯基二氮烯基取代基的偶氮类似物。在三苯基苄基氯化鏻和吡哆醇缩酮的羰基衍生物之间的 Wittig 反应中观察到的顺/反区域选择性就过渡态中间体、反应中使用的碱的性质和吡哆醇系统中的共振转化进行了讨论。偶氮衍生物通过磺胺或4-氨基苯基-1,3-二磺酸的重氮盐与相应的吡哆醇缩醛的偶氮偶联获得。获得的实验系列中的九种化合物能够发出二次谐波产生光，尽管与众所周知的 KH2PO4 或 LiIO3 钙钛矿晶体相比效率有所降低，但在激光照射下具有出色的抗光束性，这使其成为开发新型非线性光学材料的潜在起点。图形概要

  DOI：

  10.1080/00397911.2017.1422520
• 作为产物：
  描述：

  4-甲基恶唑 、 5-methanesulfonyl-4,7-dihydro-[1,3]dioxepine 反应 8.0h， 生成 Pyridoxin-formaldehydacetal
  参考文献：
  名称：

  维生素B 6 ; Diels-Alder反应的新合成†

  摘要：

  4-甲基恶唑（1a）与3-甲基磺酰基-2,5-二氢呋喃（7）进入Diels-Alder反应，其中吡reaction醇衍生物8通过消除甲亚磺酸形成。用氯化氢处理可生成二氯化物10，直接水解或通过三乙酸酯14可制得吡ido醇（12）。反应序列代表维生素B 6的丰富合成。

  DOI：

  10.1002/jlac.197919791104

文献信息

• [EN] MANUFACTURE OF VITAMIN B6<br/>[FR] FABRICATION DE LA VITAMINE B6
  申请人：DSM IP ASSETS BV

  公开号：WO2005049618A1

  公开（公告）日：2005-06-02

  A process for manufacturing a 3-unsubstituted, 3-monosubstituted or 3,3-disubstituted 9-acyloxy-1,5-dihydro-8-­methylpyrido[3,4-e] [1,3]dioxepin (I) and optionally for manufacturing pyridoxine involves performing an addition reaction between a 4-methyl-5-alkoxy-oxazole (II) and a 2-unsubstituted, 2-monosubstituted or 2,2-disubstituted 4,7-dihydro-(1,3)-dioxepin (III) in the substantial absence of a solvent and a catalyst to give a product mixture consisting essentially of the appropriate Diels-Alder adduct (IV) in a major proportion and the appropriate 3-­unsubstituted, 3-monosubstituted or 3,3-disubstituted 1,5-dihydro-8-methylpyrido[3,4-e] [1,3]dioxepin 9-ol (V) in a minor proportion, removal of a substantial proportion of the unreacted oxazole and dioxapin starting materials from the product mixture by distillation under reduced pressure, addition of a substantially anhydrous organic acid to said product mixture and rearrangement of the Diels-Alder adduct IV to further V in the presence of said substantially anhydrous organic acid with removal of the generated alkanol by distillation under reduced pressure, and acylation of the resultingly enriched quantity of V with an added carboxylic acid anhydride to produce the desired I, and optionally converting this so-manufactured acylation product I to pyridoxine by acid hydrolysis for achieving deprotection and deacylatiom. Pyridoxine is a well known form of vitamin B6 with well established utility.

  一种用于制造3-未取代，3-单取代或3,3-二取代9-酰氧基-1,5-二氢-8-甲基吡啶并[3,4-e][1,3]二氧杂环己烯(I)的方法，以及可选地用于制造吡哆醇的方法，包括在基本缺乏溶剂和催化剂的情况下，在4-甲基-5-烷氧基-噁唑酮(II)和2-未取代，2-单取代或2,2-二取代4,7-二氢-(1,3)-二氧杂环己烯(III)之间进行加成反应，以产生主要包含适当的Diels-Alder加合物(IV)和适当的3-未取代，3-单取代或3,3-二取代1,5-二氢-8-甲基吡啶并[3,4-e][1,3]二氧杂环己烯9-醇(V)的产物混合物，通过减压蒸馏去除大部分未反应的噁唑酮和二氧杂环己烯起始物，向所述产物混合物中添加基本无水的有机酸，并在所述基本无水的有机酸存在下将Diels-Alder加合物IV重排为进一步的V，并通过减压蒸馏去除生成的烷醇，将富集的V与额外的羧酸酐酸化以产生所需的I，可选择地将此种制造的酰化产物I通过酸水解转化为吡哆醇，以实现去保护和去酰基化。吡哆醇是一种已知的维生素B6形式，具有已建立的实用性。
• Novel potent pyridoxine-based inhibitors of AChE and BChE, structural analogs of pyridostigmine, with improved in vivo safety profile
  作者：Alexey D. Strelnik、Alexey S. Petukhov、Irina V. Zueva、Vladimir V. Zobov、Konstantin A. Petrov、Evgeny E. Nikolsky、Konstantin V. Balakin、Sergey O. Bachurin、Yurii G. Shtyrlin

  DOI：10.1016/j.bmcl.2016.06.070

  日期：2016.8

  We report a novel class of carbamate-type ChE inhibitors, structural analogs of pyridostigmine. A small library of congeneric pyridoxine-based compounds was designed, synthesized and evaluated for AChE and BChE enzymes inhibition in vitro. The most active compounds have potent enzyme inhibiting activity with IC50 values in the range of 0.46-2.1 mu M ( for AChE) and 0.59-8.1 mu M (for BChE), with moderate selectivity for AChE comparable with that of pyridostigmine and neostigmine. Acute toxicity studies using mice models demonstrated excellent safety profile of the obtained compounds with LD50 in the range of 22-326 mg/kg, while pyridostigmine and neostigmine are much more toxic (LD50 3.3 and 0.51 mg/kg, respectively). The obtained results pave the way to design of novel potent and safe cholinesterase inhibitors for symptomatic treatment of neuromuscular disorders. (C) 2016 Elsevier Ltd. All rights reserved.
• MANUFACTURE OF VITAMIN B6
  申请人：DSM IP Assets B.V.

  公开号：EP1685133A1

  公开（公告）日：2006-08-02
• Manufacture of vitamin b6
  申请人：Fischesser Jocelyn

  公开号：US20070072254A1

  公开（公告）日：2007-03-29

  A process for manufacturing a 3-unsubstituted, 3-monosubstituted or 3,3-disubstituted 9-acyloxy-1,5-dihydro-8-methylpyrido[3,4-e] [1,3]dioxepin (I) and optionally for manufacturing pyridoxine involves performing an addition reaction between a 4-methyl-5-alkoxy-oxazole (II) and a 2-unsubstituted, 2-monosubstituted or 2,2-disubstituted 4,7-dihydro-(1,3)-dioxepin (III) in the substantial absence of a solvent and a catalyst to give a product mixture consisting essentially of the appropriate Diels-Alder adduct (IV) in a major proportion and the appropriate 3-unsubstituted, 3-monosubstituted or 3,3-disubstituted 1,5-dihydro-8-methylpyrido[3,4-e] [1,3]dioxepin 9-ol (V) in a minor proportion, removal of a substantial proportion of the unreacted oxazole and dioxapin starting materials from the product mixture by distillation under reduced pressure, addition of a substantially anhydrous organic acid to said product mixture and rearrangement of the Diels-Alder adduct IV to further V in the presence of said substantially anhydrous organic acid with removal of the generated alkanol by distillation under reduced pressure, and acylation of the resultingly enriched quantity of V with an added carboxylic acid anhydride to produce the desired I, and optionally converting this so-manufactured acylation product I to pyridoxine by acid hydrolysis for achieving deprotection and deacylatiom. Pyridoxine is a well known form of vitamin B 6 with well established utility.
• US7495101B2
  申请人：——

  公开号：US7495101B2

  公开（公告）日：2009-02-24