2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran | 93885-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran
• 英文别名: (2-methyl-3H-1-benzofuran-2-yl)methanol
• CAS: 93885-43-9
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: GAJXHYVWKPJQDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran 在 氯化亚砜 、 jones' reagent 作用下， 以 丙酮 、 苯 为溶剂， 反应 50.5h， 生成 2-Methyl-2,3-dihydro-benzofuran-2-carbonyl chloride
  参考文献：
  名称：

  .alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity

  摘要：

  Modification of the 1,4-benzodioxan ring present in RX 781094 has not previously been considered. This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives. The dihydrobenzofuranylimidazoline compound 7 is the only analogue possessing presynaptic antagonist potency potency and selectivity comparable to that of 1. In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series. Many derivatives, as well as the parent compound 7, were found to possess presynaptic alpha 2-adrenoreceptor antagonist and postsynaptic alpha 1-adrenoreceptor partial agonist properties. Two of the selective presynaptic antagonists, 13 and 14 possess greater potency and selectivity than that possessed by 1. The 5-chloro derivative 25 is twice as potent as after oral administration but only about half as potent when given intravenously.

  DOI：

  10.1021/jm00371a003
• 作为产物：
  描述：

  甲烯丙基苯醚 在 Kieselgel 60 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.17h， 生成 2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran
  参考文献：
  名称：

  .alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity

  摘要：

  Modification of the 1,4-benzodioxan ring present in RX 781094 has not previously been considered. This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives. The dihydrobenzofuranylimidazoline compound 7 is the only analogue possessing presynaptic antagonist potency potency and selectivity comparable to that of 1. In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series. Many derivatives, as well as the parent compound 7, were found to possess presynaptic alpha 2-adrenoreceptor antagonist and postsynaptic alpha 1-adrenoreceptor partial agonist properties. Two of the selective presynaptic antagonists, 13 and 14 possess greater potency and selectivity than that possessed by 1. The 5-chloro derivative 25 is twice as potent as after oral administration but only about half as potent when given intravenously.

  DOI：

  10.1021/jm00371a003

文献信息

• Imidazoline derivatives as presynaptic .alpha..sub.2 -adrenoreceptor
  申请人：Reckitt & Colman Products Limited

  公开号：US04411908A1

  公开（公告）日：1983-10-25

  Imidazoline derivatives of the formula ##STR1## wherein R.sup.1 is hydrogen or alkyl C.sub.1-6 ; R.sup.2 is hydrogen, methyl, chloro, bromo or fluoro; R.sup.3 is hydrogen, methyl, hydroxy, methoxy, fluoro, chloro or bromo; and their non-toxic salts. Processes for their preparation and pharmaceutical compositions thereof. The compounds exhibit presynaptic .alpha..sub.2 -adrenoreceptor antagonist activity.

  咪唑啉衍生物的化学式为##STR1##其中R.sup.1为氢或烷基C.sub.1-6；R.sup.2为氢、甲基、氯、溴或氟；R.sup.3为氢、甲基、羟基、甲氧基、氟、氯或溴；以及它们的无毒盐。它们的制备方法和药物组合物。这些化合物具有前突触α2-肾上腺素受体拮抗活性。
• VO(acac)2/TBHP Catalyzed Epoxidation of 2-(2-Alkenyl)phenols. Highly Regio- and Diastereoselective Oxidative Cyclization to 2,3-Dihydro-benzofuranols and 3-Chromanols
  作者：Alessandra Lattanzi、Arrigo Scettri

  DOI：10.1055/s-2002-31894

  日期：——

  The VO(acac) 2 /TBHP (1.5 mol%/1.3 equiv) system has been successfully used for the epoxidation of variously double bond substituted 2-(2-alkenyl)phenols under mild conditions. Moreover, a one-pot conversion to 2,3-dihydrobenzofuranols and 3-chromanols is achieved with high or complete regio- and diastereoselectivity in the presence of catalytic amounts of TFA (20 mol%). This metal-catalyzed methodology

  VO(acac) 2 /TBHP (1.5 mol%/1.3 equiv) 系统已成功用于各种双键取代的 2-(2-烯基) 苯酚在温和条件下的环氧化反应。此外，在催化量的 TFA (20 mol%) 存在下，以高或完全的区域选择性和非对映选择性实现了向 2,3-二氢苯并呋喃醇和 3-苯并二氢呋喃的一锅法转化。这种金属催化的方法被证明比以前用于环氧化和 2-(2-烯基) 苯酚氧化环化的 m-CPBA 更实用和更优越。
• Imidazoline derivatives
  申请人：RECKITT AND COLMAN PRODUCTS LIMITED

  公开号：EP0071368A1

  公开（公告）日：1983-02-09

  Imidazoline derivatives of the formula wherein R' is hydrogen or alkyl C1-6; R2 is hydrogen, methyl, chloro, bromo or fluoro; R3 is hydrogen, methyl, hydroxy, methoxy, fluoro, chloro or bromo; and their non-toxic salts. Processes for their preparation and pharmaceutical compositions thereof. The compounds exhibit presynaptic α2-adrenoreceptor antagonist activity.

  式中R'为氢或C1-6烷基；R2为氢、甲基、氯、溴或氟；R3为氢、甲基、羟基、甲氧基、氟、氯或溴的咪唑啉衍生物及其无毒盐。 其制备方法及其药物组合物。 这些化合物具有突触前α2-肾上腺素受体拮抗剂活性。
• US4411908A
  申请人：——

  公开号：US4411908A

  公开（公告）日：1983-10-25
• .alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity
  作者：Christopher B. Chapleo、Peter L. Myers、Richard C. M. Butler、John A. Davis、John C. Doxey、Stanley D. Higgins、Malcolm Myers、Alan G. Roach、Colin F. C. Smith

  DOI：10.1021/jm00371a003

  日期：1984.5

  Modification of the 1,4-benzodioxan ring present in RX 781094 has not previously been considered. This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives. The dihydrobenzofuranylimidazoline compound 7 is the only analogue possessing presynaptic antagonist potency potency and selectivity comparable to that of 1. In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series. Many derivatives, as well as the parent compound 7, were found to possess presynaptic alpha 2-adrenoreceptor antagonist and postsynaptic alpha 1-adrenoreceptor partial agonist properties. Two of the selective presynaptic antagonists, 13 and 14 possess greater potency and selectivity than that possessed by 1. The 5-chloro derivative 25 is twice as potent as after oral administration but only about half as potent when given intravenously.