(2S)-3-(邻烯丙基氧基苯氧基)-1,2-环氧丙烷 | 66966-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (2S)-3-(邻烯丙基氧基苯氧基)-1,2-环氧丙烷
• 英文名称: (S)-3-(2-allyloxyphenoxy)-1,2-epoxypropane
• 英文别名: (S)-o-allyloxyphenyl glycidyl ether；(S)-glycidyl-2-allyloxyphenyl ether；(2S)-3-(O-Allyloxyphenoxy)-1,2-epoxypropane；(2S)-2-[(2-prop-2-enoxyphenoxy)methyl]oxirane
• CAS: 66966-20-9
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: FZONULHLKBOHHY-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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)-3-(邻烯丙基氧基苯氧基)-1,2-环氧丙烷 、 异丙胺 以 四氢呋喃 、 乙醇 为溶剂， 反应 12.0h， 生成 (S)-oxprenolol
  参考文献：
  名称：

  酶辅助制备对映体纯的β-肾上腺素能阻滞剂III。旋光氯醇衍生物及其转化

  摘要：

  两个对映体系列的光学活性氯代醇衍生物2a-m和3a-m是通过酶水解和由假单胞菌属物种的高度选择性脂肪酶催化的酰基转移反应制备的。。将得到的结构单元进一步转化为高对映体纯度的相应β-受体阻滞剂。

  DOI：

  10.1016/s0957-4166(00)80256-6
• 作为产物：
  描述：

  3-(o-Allyloxyphenoxy)-2-hydroxy-1-chlorpropan 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2S)-3-(邻烯丙基氧基苯氧基)-1,2-环氧丙烷
  参考文献：
  名称：

  酶辅助制备对映体纯的β-肾上腺素能阻滞剂III。旋光氯醇衍生物及其转化

  摘要：

  两个对映体系列的光学活性氯代醇衍生物2a-m和3a-m是通过酶水解和由假单胞菌属物种的高度选择性脂肪酶催化的酰基转移反应制备的。。将得到的结构单元进一步转化为高对映体纯度的相应β-受体阻滞剂。

  DOI：

  10.1016/s0957-4166(00)80256-6

文献信息

• PROCESS FOR THE PREPARATION OF 3-AMINO-2-HYDROXY-1-PROPYL ETHERS
  申请人：DAISO CO., LTD.

  公开号：EP0930291A1

  公开（公告）日：1999-07-21

  A process for preparation of 3-amino-2-hydroxy-1-propyl ether of the formula wherein R1 is substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic ring, R2 and R3 are the same or different hydrogen atom, a substituted or unsubstituted alkyl, or may form a ring together with an adjacent nitrogen atom, which ring may be interrupted with nitrogen atom, oxygen atom or sulfur atom, which is characterized in reacting an epoxy compound of the formula wherein X is halogen, in the presence of a fluoride salt, with an alcohol and then reacting an amine. According to the above method, an intermediates for synthesis of medicines is obtained in good yield and highly optical purity.

  一种制备式 3-氨基-2-羟基-1-丙基醚的工艺 其中 R1 是取代或未取代的烷基、取代或未取代的芳基或取代或未取代的杂环，R2 和 R3 是相同或不同的氢原子、取代或未取代的烷基，或可与相邻的氮原子一起形成环，该环可被氮原子、氧原子或硫原子打断、 其特征在于使式如下的环氧化合物反应 其中 X 为卤素 的环氧化合物与醇反应，然后与胺反应。 根据上述方法，可以获得产率高、光学纯度高的药物合成中间体。
• CsF in organic synthesis. Regioselective nucleophilic reactions of phenols with oxiranes leading to enantiopure β-blockers
  作者：Kazuhiro Kitaori、Yoshiro Furukawa、Hiroshi Yoshimoto、Junzo Otera

  DOI：10.1016/s0040-4020(99)00896-0

  日期：1999.12

  The two modes of the paths in the reaction of oxiranes with phenols are completely controlled by CsF. Glycidyl nosylate undergoes exclusive substitution at the C-1 position whereas the ring-opening (C-3 attack) occurs with epichlorohydrin, glycidol, and 1,2-epoxyalkanes. These reactions provide convenient access to enantiopure beta-blockers. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Determination of the enantiomeric purity and the configuration of β-aminoalcohols using (R)-2-fluorophenylacetic acid (AFPA) and fluorine-19 NMR: application to β-blockers
  作者：Marcel Apparu、Younes Ben Tiba、Pierre-Marc Léo、Sylvain Hamman、Christian Coulombeau

  DOI：10.1016/s0957-4166(00)00254-8

  日期：2000.7

  A method has been developed for determining the enantiomeric purity and the absolute configuration of beta-aminoalcohols of type ArOCH2CH(OH)CH2NHR (R = iPr, tBu). To determine enantiomeric purity, the amine function was first protected by a benzyl group, then the compound formed was esterified using the acid chloride of (R)-2-fluorophenylacetic acid (AFPA). The F-19 NMR analysis of the derivative obtained revealed the presence of two distinctly separate signals (similar to 2.5 ppm), the one for the RS-SR pair being the most deshielded. The configuration was determined directly on the aminoalcohol by using the acid. In stoichiometric conditions, when R = iPr, the amide function was obtained very preponderantly. The F-19 NMR spectrum of the amide presented four distinct signals when derivatization was carried out by means of a reaction between the (+/-)-beta-aminoalcohol and the (R)-AFPA. The extreme signals, which were over 3.5 ppm apart, did not belong to the same diastereomer. With R = tBu essentially the ester function was obtained. The first studies revealed the presence of two signals, though not as clearly separated as in the previous cases. Each experiment was simple to perform, and purification was not necessary. Mosher's acid gave unsatisfactory results in each case. (C) 2000 Elsevier Science Ltd. All rights reserved.
• CsF in organic synthesis. The first and convenient synthesis of enantiopure bisoprolol by use of glycidyl nosylate
  作者：Kazuhiro Kitaori、Yoshiro Furukawa、Hiroshi Yoshimoto、Junzo Otera

  DOI：10.1016/s0040-4039(98)00452-3

  日期：1998.5

  The regioselective substitution of glycidyl nosylate with phenols is catalyzed by CsF in the presence of K2CO3 in DMF; this reaction enables the first and convenient synthesis of enantiopure bisoprolol. (C) 1998 Elsevier Science Ltd. All rights reserved.
• PROCESS FOR PRODUCING GLYCIDYL ETHER
  申请人：DAISO CO., LTD.

  公开号：EP1508568B1

  公开（公告）日：2010-11-03