(2S,1'R)-2-oxiranyl-1,4-benzodioxan | 81703-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: (2S,1'R)-2-oxiranyl-1,4-benzodioxan
• 英文别名: (3S)-3-[(2R)-oxiran-2-yl]-2,3-dihydro-1,4-benzodioxine
• CAS: 81703-47-1
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: LDWQUOIUYGBUPN-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,1'R)-2-oxiranyl-1,4-benzodioxan 在 sodium tetrahydroborate 、 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 生成 (R)-2-(羟基甲基)-1,4-苯并二噁烷
  参考文献：
  名称：

  Serotonergic properties of spiroxatrine enantiomers

  摘要：

  The neuroleptic drug spiperone (1) has proven very useful in the characterization of putative serotonin (5-hydroxytryptamine, 5-HT) receptors. Thus, 5-HT1 receptors have been divided into subtypes based on their affinities for 1: 5-HT1A sites have high affinity, while 5-HT1B sites have low affinity. However, the usefulness of 1 for the pharmacological characterization of 5-HT1A sites is limited because of its high affinity for 5-HT2 (as well as D2-dopaminergic) receptors. A close analogue of 1, (+/-)-spiroxatrine (2), has much higher affinity for 5-HT1A receptors and much lower affinity for 5-HT2 receptors. We report here the stereospecific synthesis of (R)-(+)- and (S)-(-)-spiroxatrine enantiomers and their evaluation at several 5-HT receptors and D2-dopaminergic and alpha 1-adrenergic receptors.

  DOI：

  10.1021/jm00118a017
• 作为产物：
  描述：

  2-苯甲氧基苯酚 在 palladium on activated charcoal 吡啶 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 氢氧化钾 、 氢气 、 二异丁基氢化铝 、 potassium carbonate 、 (+)-Weinsaeure-diethylester 作用下， 以 甲醇 、 乙醚 、 正己烷 、 丁酮 为溶剂， -20.0~25.0 ℃ 、344.73 kPa 条件下， 反应 38.5h， 生成 (2S,1'R)-2-oxiranyl-1,4-benzodioxan
  参考文献：
  名称：

  Clark, Robin D.; Kurz, Lilia J., Heterocycles, 1985, vol. 23, # 8, p. 2005 - 2012

  摘要：

  DOI：

文献信息

• Antihypertensive 1-Acyl-4-[2-(1,4-benzodioxan-2-yl)-2-hydroxyethylamino]piperidines
  作者：Joan M. Caroon、Robin D. Clark、David B. Repke、Arthur F. Kluge、Arthur M. Strosberg、Roger L. Whiting、Marlys D. Okada、Linda R. Hedley、Donna van Antwerp、Christine M. Brown

  DOI：10.1002/jps.2600760110

  日期：1987.1

  Several 1-acyl-4-[2-(1,4-benzodioxan-2-yl)-2-hydroxy-ethylamino]piperidine s were prepared and a number of the compounds showed antihypertensive activity in the spontaneously hypertensive rat (SHR). This activity was specific for the (2S, 2R) enantiomers. General pharmacological evaluation and ligand binding data on selected compounds indicated a moderate degree of alpha 1- and beta-antagonistic activity

  制备了几种1-酰基-4- [2-（1，4-苯并二恶烷-2-基）-2-羟基-乙基氨基]哌啶，并且许多化合物在自发性高血压大鼠（SHR）中显示出降压活性。该活性对（2S，2R）对映异构体是特异性的。关于所选化合物的一般药理评估和配体结合数据表明，α1和β拮抗活性的程度适中。α1拮抗作用可能不足以解释SHR中的降血压活性。
• Antihypertensive 9-substituted 1-0xa-4,9-diazaspiro[5.5]undecan-3-ones
  作者：Robin D. Clark、Joan M. Caroon、David B. Repke、Arthur M. Strosberg、Susan M. Bitter、Marlys D. Okada、Anton D. Michel、Roger L. Whiting

  DOI：10.1021/jm00360a013

  日期：1983.6

  Forty-one 9-substituted 1-oxa-4,9-diazaspiro[5.5]undecan-3-ones were prepared for antihypertensive screening in the spontaneously hypertensive rat (SHR). For the 9-(2-indol-3-ylethyl) series, the parent compound, 9-(2-indol-3-ylethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-3-one (21), was the most potent antihypertensive agent. Substitution of lower alkyl groups on the spirolactam ring gave compounds close in activity to 21, while substitution with large alkyl or aryl groups led to a significant decrease in activity. Ring-opened analogues of 21 that contained the same functionality were markedly less active. Several 1-oxa-4,9-diazaspiro[5.5]undecan-3-ones substituted at the 9 position with 1,4-benzodioxan-2-ylmethyl, 1,4-benzodioxan-2-ylhydroxyethyl, and 2-phenylethyl groups also demonstrated significant activity. Compound 21 was chosen for a detailed pharmacological evaluation. Its antihypertensive activity appears to be predominantly due to peripheral alpha 1-adrenoceptor blockade.
• HUEBNER, C. F.;GSCHWEND, H. W.
  作者：HUEBNER, C. F.、GSCHWEND, H. W.

  DOI：——

  日期：——
• ROSZKOWSKI, A. P.;CLARK, R. D.;KLUGE, A. F.
  作者：ROSZKOWSKI, A. P.、CLARK, R. D.、KLUGE, A. F.

  DOI：——

  日期：——
• CALARK, R. D.;CAROON, J. M.;KLUGE, A. F.;REPKE, D. B.;ROSZKOWSKI, A. P.;S+, J. MED. CHEM., 1983, 26, N 5, 657-661
  作者：CALARK, R. D.、CAROON, J. M.、KLUGE, A. F.、REPKE, D. B.、ROSZKOWSKI, A. P.、S+

  DOI：——

  日期：——