(5R)-5-[(1S)-1,2-dihydroxyethyl]butyrolactone | 137625-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (5R)-5-[(1S)-1,2-dihydroxyethyl]butyrolactone
• 英文别名: 2,3-dideoxy-L-erythro-hexono-1,4-lactone；2.3-dideoxy-L-erythro-hexono-1,4-lactone；(5R)-5-[(1S)-1,2-dihydroxyethyl]oxolan-2-one
• CAS: 137625-43-5
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: WKCBOODKPXKQAC-CRCLSJGQSA-N

物化性质

• 沸点：
  410.9±15.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R)-5-[(1S)-1,2-dihydroxyethyl]butyrolactone 在 sodium tetrahydroborate 、 sodium periodate 、 silica gel 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 0.17h， 生成 (R)-γ-羟甲基-γ-丁内酯 (R)-4,5-二氢-5-羟甲基-2(3H)-呋喃酮 (R)-5-羟甲基-2-氧代四氢呋喃
  参考文献：
  名称：

  制备新型合成子，独特官能化的四氢呋喃和四氢吡喃衍生物。

  摘要：

  乙酰乙酸酯的二价阴离子与表溴醇衍生物反应，得到（Z）-2-烷氧基羰基亚甲基四氢呋喃衍生物和（E）-2-烷氧基羰基亚甲基四氢吡喃衍生物的混合物。通过使用LiClO4作为添加剂可以选择性地形成四氢呋喃衍生物。还检查了旋光四氢呋喃衍生物和四氢吡喃衍生物的制备，并阐明了产物的光学纯度和绝对构型。

  DOI：

  10.1248/cpb.48.1581
• 作为产物：
  描述：

  (5R)-5-[(1S)-1-hydroxy-2-phenylmethoxyethyl]oxolan-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.5h， 生成 (5R)-5-[(1S)-1,2-dihydroxyethyl]butyrolactone
  参考文献：
  名称：

  制备新型合成子，独特官能化的四氢呋喃和四氢吡喃衍生物。

  摘要：

  乙酰乙酸酯的二价阴离子与表溴醇衍生物反应，得到（Z）-2-烷氧基羰基亚甲基四氢呋喃衍生物和（E）-2-烷氧基羰基亚甲基四氢吡喃衍生物的混合物。通过使用LiClO4作为添加剂可以选择性地形成四氢呋喃衍生物。还检查了旋光四氢呋喃衍生物和四氢吡喃衍生物的制备，并阐明了产物的光学纯度和绝对构型。

  DOI：

  10.1248/cpb.48.1581

文献信息

• Stereoselective process for the preparation of 2-amino-ethanol
  申请人：Zambon Group S.p.A

  公开号：US05142066A1

  公开（公告）日：1992-08-25

  A stereoselective process for the preparation of the compounds of formula ##STR1## wherein R, R.sub.1, R.sub.2, a and b have the meanings reported in the specification, is described. The compounds of formula I have a remarkable central analgesic activity and they are useful in the pharmaceutical field.

  本发明提供了一种立体选择性的方法，用于制备公式##STR1##中R、R.sub.1、R.sub.2、a和b的化合物。其中R、R.sub.1、R.sub.2、a和b的含义在说明书中有所描述。公式I的化合物具有显著的中枢镇痛活性，并且在制药领域中有用。
• Conformationally Constrained Analogues of Diacylglycerol. 13. Protein Kinase C Ligands Based on Templates Derived from 2,3-Dideoxy-<scp>l</scp>-<i>erythro(threo)</i>-hexono-1,4-lactone and 2-Deoxyapiolactone
  作者：Jeewoo Lee、Nancy E. Lewin、Peter Acs、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm960525v

  日期：1996.1.1

  In the present investigation, the last two possible modes of generating conformationally semirigid diacylglycerol (DAG) analogues embedded into five-membered ring lactones as templates III and IV are investigated. The first two templates studied in previous investigations corresponded to 2-deoxyribonolactone (template I) and 4,4-disubstituted gamma-butyrolactone (template II), with the latter producing potent protein kinase C (PK-C) ligands with low nanomolar binding affinities. The templates reported in this work correspond to 2,3-dideoxy-L-erythro- or -threo-hexono-1,4-lactone (template III) and 2-deoxyapiolactone (template IV). Compounds constructed with the dideoxy-L-erythro- or -threo-hexono-1,4-lactone template were synthesized stereospecifically from tri-O-acetyl-L-glucal and L-galactono-1,4-lactone, respectively. Compounds constructed with the 2-deoxyapiolactone template were synthesized stereoselectively from di-O-isopropylidene-alpha-D-apiose. Inhibition of the binding of [H-3]phorbol-12,13-dibutyrate to PK-C alpha showed that only the threo-isomer, 5-O-tetradecanoyl-2,3-dideoxy-L-threo-hexono-1,4-lactone (2) was a good PK-C ligand (K-i = 1 mu M). The rest of the ligands had poorer affinities with K-i values between 10 and 28 mu M. With these results, the order of importance of five-membered ring lactones as competent templates for the construction of semirigid DAG surrogates with effective PK-C binding affinity can be established as II much greater than I similar to III > IV.
• Stereoselective process for the preparation of 2-amino-ethanol derivatives having a central analgesic activity and intermediates thereof
  申请人：ZAMBON GROUP S.p.A.

  公开号：EP0449011B1

  公开（公告）日：1997-10-08
• US5142066A
  申请人：——

  公开号：US5142066A

  公开（公告）日：1992-08-25