4-叠氮丁烷-1,2-二醇 | 114642-93-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 4-叠氮丁烷-1,2-二醇
• 英文名称: 4-azidobutane-1,2-diol
• 英文别名: 4-azidobutan-1,2-diol
• CAS: 114642-93-2
• 化学式: C₄H₉N₃O₂
• 分子量: 131.134
• InChiKey: CBRREUPPRHQWCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-叠氮丁烷-1,2-二醇 在 sodium periodate 作用下， 以 水 为溶剂， 反应 0.5h， 以11 g的产率得到3-叠氮丙醛
  参考文献：
  名称：

  同源的ω-氨基化的1-甲氧基烷基β-D-吡喃葡萄糖苷的合成，作为潜在的β-D-葡萄糖苷酶抑制剂。

  摘要：

  （R）-和（S）-2-叠氮基-1-甲氧基乙基β-D-吡喃葡萄糖苷（16）和（17），（R）-和（S）-3-叠氮基-1-甲氧基丙基-β-D-吡喃葡萄糖苷（18）和（19），（R，S）-4-叠氮基-1-甲氧基丁基β-D-吡喃葡萄糖苷（20）和（R，S）-5-叠氮基-1-甲氧基戊基β-D-吡喃葡萄糖苷（ 22）由乙醛，丙醛，丁醛和戊醛的ω-取代的二甲基乙缩醛通过三甲基甲硅烷基三氟甲磺酸酯催化的转缩醛反应使用1-O-三甲基甲硅烷基2,3,4,6-四-O-乙酰基-β-D-葡萄糖合成（1）作为接受人。多数乙酰化的（R，S）-受体均可以通过柱色谱法分离为纯化合物。初步测试表明，在糖苷配基中带有ω-溴，叠氮基或乙酰氨基取代基的脱乙酰基缩醛糖苷是甜杏仁中β-D-葡萄糖苷酶的良好底物。化合物16、19、20和22的相应ω-氨基衍生物，（R）-2-氨基-1-甲氧基乙基β-D-吡喃葡萄糖苷（23），（S）-3-氨基-1-甲氧基丙基β-

  DOI：

  10.1016/0008-6215(87)80242-2
• 作为产物：
  描述：

  4-叠氮基-1-丁烯 在 hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether 作用下， 以77%的产率得到4-叠氮丁烷-1,2-二醇
  参考文献：
  名称：

  New Asymmetric Synthesis of Enantiomeric Pairs of the 2-Substituted Pyrrolidines Bgugaine and Irniine

  摘要：

  A new asymmetric route to 2-substituted pyrrolidines starting with the Sharpless asymmetric dihydroxylation (AD) of 4-pentenylphthalimide (5) followed by aminocyclization of the resultant amino alcohol is presented. The application to the asymmetric synthesis has been examined for two 2-substituted pyrrolidine alkaloids, bgugaine (1) and irniine (2).

  DOI：

  10.3987/com-97-s26

文献信息

• Synthesis of Regioisomeric Azidobutanediols
  作者：Bernhard Wünsch、Marion Aepkers

  DOI：10.1055/s-2004-822329

  日期：——

  Investigations to control the regioselectivity during the acetalization of pivalaldehyde (7) with butane-1,2,4-triol (4) were performed. Thermodynamic control led to the regioisomeric acetals 8 and 9 in the ratio 76:24, whereas kinetic control favored the five-membered acetal 9 (8/9 30:70). Tosylation, nucleophilic substitution with NaN3, and subsequent methanolysis of the regioisomeric acetals 8 and 9 provided the regioisomeric 4-azidobutanediols 5 and 6, which are considered as valuable building blocks for the synthesis of novel NMDA-receptor antagonists.

  研究人员对新戊醛（7）与丁烷-1,2,4-三醇（4）乙缩醛化过程中的区域选择性进行了控制。在热力学控制下，生成了比例为 76:24 的异构乙缩醛 8 和 9，而在动力学控制下，则生成了五元乙缩醛 9（8/9 30:70）。通过对甲苯磺酸化、NaN3 亲核取代以及随后的甲醇分解，得到了 4-叠氮丁二醇 5 和 6，它们被认为是合成新型 NMDA 受体拮抗剂的重要组成单元。
• Structure–affinity relationship studies of non-competitive NMDA receptor antagonists derived from dexoxadrol and etoxadrol
  作者：Marion Aepkers、Bernhard Wünsch

  DOI：10.1016/j.bmc.2005.07.030

  日期：2005.12

  The synthesis and NMDA receptor affinity of ring and side-chain homologues of etoxadrol and dexoxadrol are described. For the regioselective synthesis of etoxadrol homologues, the regioisomeric 4-azidobutanediols (+/-)-9 and (+/-)-14 were employed. A synthesis of the enantiomerically pure azidobutanediols (S)-, (R)-9 and (S)-, (R)-14 was developed and the homochiral building blocks were used for the synthesis of enantiomerically pure etoxadrol and dexoxadrol homologues. The affinity of the racemic and enantiomerically pure primary amines toward the phencyclidine binding site of the NMDA receptor was investigated in receptor binding studies with tritium labeled [H-3]-(+)-MK-801 as radioligand. Benzaldehyde derivatives (+/-)-12a, (+/-)-13a, and (+/-)-16a bearing a proton at the acetalic position do not interact significantly with the NMDA receptor. An enantioselective NMDA receptor binding was observed for the trans-configured 2-(2-ethyl-2-phenyl-1,3-dioxolan-4-yl)ethanamine 13b, the (2-ethyl-2-phenyl-1,3-dioxan-4-yl)methanamine 16b, and the (2,2-diphenyl-1,3-dioxan-4-yl)methanamine 16c. The NMDA receptor affinity of these compounds resides almost exclusively in the (S)-configured enantiomers (2S,4S)-13b, (2S,4S)-16b, and (4S)-16c. The lowest K-i-value in this series was found for the (2S,4S)-configured 1,3-dioxolane (2S,4S)-13b (K-i = 69 nM), which is in the range of the Ki-value of the lead compounds etoxadrol and dexoxadrol, indicating that the 2-aminoethyl and the piperidin-2-yl substituents lead to similar NMDA receptor interactions. (c) 2005 Elsevier Ltd. All rights reserved.
• Syntheses of homologous ω-aminated 1-methoxyalkyl β-D-glucopyranosides as potential β-D-glucosidase inhibitors
  作者：Jochen Lehmann、Lothar Ziser

  DOI：10.1016/0008-6215(87)80242-2

  日期：1987.11

  (R)- and (S)-2-Azido-1-methoxyethyl beta-D-glucopyranosides (16) and (17), (R)- and (S)-3-azido-1-methoxypropyl beta-D-glucopyranosides (18) and (19), (R,S)-4-azido-1-methoxybutyl beta-D-glucopyranoside (20), and (R,S)-5-azido-1-methoxypentyl beta-D-glucopyranoside (22) were synthesized from omega-substituted dimethyl acetals of acetaldehyde, propanal, butanal, and pentanal by trimethylsilyl triflate-catalysed

  （R）-和（S）-2-叠氮基-1-甲氧基乙基β-D-吡喃葡萄糖苷（16）和（17），（R）-和（S）-3-叠氮基-1-甲氧基丙基-β-D-吡喃葡萄糖苷（18）和（19），（R，S）-4-叠氮基-1-甲氧基丁基β-D-吡喃葡萄糖苷（20）和（R，S）-5-叠氮基-1-甲氧基戊基β-D-吡喃葡萄糖苷（ 22）由乙醛，丙醛，丁醛和戊醛的ω-取代的二甲基乙缩醛通过三甲基甲硅烷基三氟甲磺酸酯催化的转缩醛反应使用1-O-三甲基甲硅烷基2,3,4,6-四-O-乙酰基-β-D-葡萄糖合成（1）作为接受人。多数乙酰化的（R，S）-受体均可以通过柱色谱法分离为纯化合物。初步测试表明，在糖苷配基中带有ω-溴，叠氮基或乙酰氨基取代基的脱乙酰基缩醛糖苷是甜杏仁中β-D-葡萄糖苷酶的良好底物。化合物16、19、20和22的相应ω-氨基衍生物，（R）-2-氨基-1-甲氧基乙基β-D-吡喃葡萄糖苷（23），（S）-3-氨基-1-甲氧基丙基β-
• New Asymmetric Synthesis of Enantiomeric Pairs of the 2-Substituted Pyrrolidines Bgugaine and Irniine
  作者：Hiroki Takahata、Kozue Ihara、Minoru Kubota、Takefumi Momose

  DOI：10.3987/com-97-s26

  日期：——

  A new asymmetric route to 2-substituted pyrrolidines starting with the Sharpless asymmetric dihydroxylation (AD) of 4-pentenylphthalimide (5) followed by aminocyclization of the resultant amino alcohol is presented. The application to the asymmetric synthesis has been examined for two 2-substituted pyrrolidine alkaloids, bgugaine (1) and irniine (2).