(±)-trans-(1-benzyl-azetidine-2,4-diyl)dimethanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (±)-trans-(1-benzyl-azetidine-2,4-diyl)dimethanol
• 英文别名: (+/-)-(2R,4R)-N-benzyl-2,4-bis(hydroxymethyl)azetidine；(2R*,4R*)-1-benzylazetidine-2,4-dimethanol；(+/-)-N-benzyl-2,4-trans-2,4-bis(hydroxymethyl)azetidine；[(2S,4S)-1-benzyl-4-(hydroxymethyl)azetidin-2-yl]methanol
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: STVDKEPRJUNWSZ-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (±)-trans-(1-benzyl-azetidine-2,4-diyl)dimethanol 在 盐酸 、 甲醇 、 水 作用下， 以 乙醇 为溶剂， 反应 0.41h， 生成 (+/-)-(2R,4R)-1-[(7-benzyloxymethyl-9-deaza-6-methoxypurin-9-yl)methyl]azetidine-2,4-dimethanol hydrochloride
  参考文献：
  名称：

  WO2008/79028

  摘要：

  公开号：
• 作为产物：
  描述：

  2,4-二溴戊二酸二乙酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 苯 为溶剂， 反应 28.0h， 生成 (±)-trans-(1-benzyl-azetidine-2,4-diyl)dimethanol
  参考文献：
  名称：

  Synthesis of chiral non-racemic azetidines by lipase-catalysed acetylations and their transformation into amino alcohols: precursors of chiral catalysts

  摘要：

  Azetidinic mono-acetate 7, diol 6b and di-acetate 10a were prepared with high e.e. using PPL-catalysed acetylations. The absolute configurations of all new enantioenriched compounds were assigned by chemical correlation with known compounds. Mono-acetate 7 was then transformed into 30, an amino alcohol of noteworthy potential interest since it represents an interesting precursor for chiral catalysts, such as 32. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00077-5

文献信息

• Azetidine Based Transition State Analogue Inhibitors of <i>N</i>-Ribosyl Hydrolases and Phosphorylases
  作者：Gary B. Evans、Richard H. Furneaux、Ben Greatrex、Andrew S. Murkin、Vern L. Schramm、Peter C. Tyler

  DOI：10.1021/jm701265n

  日期：2008.2.1

  ribooxacarbenium carbon from the fixed purine to phosphate and water nucleophiles, respectively. As the lysis reaction progresses along the reaction coordinate, the distance between the purine and carbocation increases and the distance between carbocation and nucleophile decreases. Immucillin-H and DADMe-immucillin-H have been shown previously to be potent inhibitors of purine nucleoside phosphorylases and lie more

  N-核糖基磷酸化酶和水解酶通过将阳离子核糖氧碳carb碳分别从固定的嘌呤迁移到磷酸和水亲核试剂来催化亲核取代反应。随着裂解反应沿着反应坐标进行，嘌呤和碳正离子之间的距离增加，而碳正离子和亲核试剂之间的距离减小。以前已显示Immucillin-H和DADMe-immucillin-H是嘌呤核苷磷酸化酶的有效抑制剂，分别位于该反应坐标的反应物和产物侧。目前正在人类临床试验中针对不同适应症的这两种酶抑制剂都是手性的且制造昂贵。现在，我们报告DADMe-immucillins的氮杂环丁烷类似物的合成，
• Synthesis and evaluation of novel azetidine analogs as potent inhibitors of vesicular [3H]dopamine uptake
  作者：Derong Ding、Justin R. Nickell、Agripina G. Deaciuc、Narsimha Reddy Penthala、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1016/j.bmc.2013.08.001

  日期：2013.11

  Lobelane analogs that incorporate a central piperidine or pyrrolidine moiety have previously been reported by our group as potent inhibitors of VMAT2 function. Further central ring size reduction of the piperidine moiety in lobelane to a four-membered heterocyclic ring has been carried out in the current study to afford novel cis-and trans-azetidine analogs. These azetidine analogs (15a-15c and 22a-22c) potently inhibited [H-3]dopamine (DA) uptake into isolated synaptic vesicles (K-i <= 66 nM). The cis-4-methoxy analog 22b was the most potent inhibitor (K-i = 24 nM), and was twofold more potent that either lobelane (2a, K-i = 45 nM) or norlobelane (2b, K-i = 43 nM). The trans-methylenedioxy analog, 15c (K-i = 31 nM), was equipotent with the cis-analog, 22b, in this assay. Thus, cis-and trans-azetidine analogs 22b and 15c represent potential leads in the discovery of new clinical candidates for the treatment of methamphetamine abuse. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of optically active N-benzyl-2,4-bis(hydroxymethyl) substituted azetidines by lipase catalyzed acetylations
  作者：Giuseppe Guanti、Renata Riva

  DOI：10.1016/0957-4166(95)00387-8

  日期：1995.12

  Both cis- and trans-N-benzyl-azetidine-2,4-dimethanols 5 and 6 were prepared and submitted to acetylation in organic solvents catalyzed by lipases. Asymmetrization of diol 5 gave the corresponding monoacetate 7, while double sequential kinetic resolution of racemic 6 gave optically enriched diol 6b and its enantiomer as the corresponding diacetate 10a Optimized reaction conditions furnished 7, 6b and 10a with e.e. > 99%.
• NOVEL CYCLIC LIPID DERIVATIVES AS POTENT PAF ANTAGONISTS
  申请人：POHANG IRON & STEEL CO., LTD.

  公开号：EP0607374B1

  公开（公告）日：1999-04-07
• US5610310A
  申请人：——

  公开号：US5610310A

  公开（公告）日：1997-03-11