(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
• Preparation of Novel Synthons, Uniquely Functionalized Tetrahydrofuran and Tetrahydropyran Derivatives.
  作者：Masahisa NAKADA、Masashi TAKANO、Yukitaka IWATA

  DOI：10.1248/cpb.48.1581

  日期：——

  with epibromohydrin derivatives to afford a mixture of (Z)-2-alkoxycarbonylmethylidenetetrahydrofuran derivative and (E)-2-alkoxycarbonylmethylidenetetrahydropyran derivative. The selective formation of the tetrahydrofuran derivative is achieved by the use of LiClO4 as the additive. The preparation of the optically active tetrahydrofuran derivatives and tetrahydropyran derivatives is also examined, and

  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。