threo-oxiran-2'(R)-ylethan-1(R)-ol | 53837-90-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: threo-oxiran-2'(R)-ylethan-1(R)-ol
• 英文别名: (R^*,R^*)-α-Methyloxiranemethanol；(1R)-1-(oxiran-2-yl)ethanol
• CAS: 53837-90-4
• 化学式: C₄H₈O₂
• 分子量: 88.1063
• InChiKey: LEJLUUHSOFWJSW-SYPWQXSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Chloro-5-(3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-N-(1-hydroxy-cycloheptylmethyl)-benzamide 、 threo-oxiran-2'(R)-ylethan-1(R)-ol 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-氯-N-[(1-羟基环庚基)甲基]-5-{4-[(R)-羟基(甲氧基)甲基]-3,5-二氧代-4,5-二氢-1,2,4-三嗪-2(3H)-基}苯甲酰胺
  参考文献：
  名称：

  Optimization of the physicochemical and pharmacokinetic attributes in a 6-azauracil series of P2X7 receptor antagonists leading to the discovery of the clinical candidate CE-224,535

  摘要：

  High throughput screening (HTS) of our compound file provided an attractive lead compound with modest P2X(7) receptor antagonist potency and high selectivity against a panel of receptors and channels, but also with high human plasma protein binding and a predicted short half-life in humans. Multi-parameter optimization was used to address the potency, physicochemical and pharmacokinetic properties which led to potent P2X(7)R antagonists with good disposition properties. Compound 33 (CE-224,535) was advanced to clinical studies for the treatment of rheumatoid arthritis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.077
• 作为产物：
  描述：

  ((2S,3R)-3-methyloxiran-2-yl)methanol 在 potassium carbonate 作用下， 反应 0.75h， 生成 threo-oxiran-2'(R)-ylethan-1(R)-ol
  参考文献：
  名称：

  Marstokk, K.-M.; Moellendal, Harald; Samdal, Svein, Acta Chemica Scandinavica, 1992, vol. 46, # 4, p. 325 - 337

  摘要：

  DOI：

文献信息

• Stereocontrolled synthesis of the C(1)-C(17) half of boromycin
  作者：James D. White、Mitchell A. Avery、Satish C. Choudhry、Om P. Dhingra、Myung Chol Kang、Alan J. Whittle

  DOI：10.1021/ja00359a041

  日期：1983.10
• Photooxygenation of olefins in the presence of titanium(IV) catalyst. A convienient "one-pot" synthesis of epoxy alcohols.
  作者：Waldemar Adam、Martin Braun、Axel Griesbeck、Vittorio Lucchini、Eugen Staab、Bernd Will

  DOI：10.1021/ja00183a032

  日期：1989.1
• Asymmetric dihydroxylation of primary allylic halides and a concise synthesis of (−)-diepoxybutane
  作者：Koen P.M. Vanhessche、Zhi-Min Wang、K.Barry Sharpless

  DOI：10.1016/s0040-4039(00)73212-6

  日期：1994.5

  Tire asymmetric dihydroxylation (AD) of primary allylic halides is described. Enantiomeric excesses range from 40 to 98%. Subsequent base treatment gives epoxy alcohols in high yields. This strategy is further illustrated by the synthesis of (-)-diepoxybutane, an important C-4-chiral building block.