methyl (S)-4-oxiranylmethoxybenzoate | 154872-58-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (S)-4-oxiranylmethoxybenzoate
• 英文别名: (S)-glycidyl p-methoxycarbonylphenyl ether；Benzoic acid, 4-[(2S)-oxiranylmethoxy]-, methyl ester；methyl 4-[[(2S)-oxiran-2-yl]methoxy]benzoate
• CAS: 154872-58-9
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: GVMPCQYYYYFGMV-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-(+)-对硝基苯磺酸缩水甘油酯 、 对羟基苯甲酸甲酯 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以97%的产率得到methyl (S)-4-oxiranylmethoxybenzoate
  参考文献：
  名称：

  CsF in organic synthesis. The first and convenient synthesis of enantiopure bisoprolol by use of glycidyl nosylate

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(98)00452-3

文献信息

• Synthesis and Structure-Activity Relationship of 4-Substituted Benzoic Acids and their Inhibitory Effect on the Biosynthesis of Fatty Acids and Sterols
  作者：Tomoyasu Ohno、Kazuo Ogawa、Shingo Yano、Masakazu Fukushima、Norihiko Suzuki、Tetsuji Asao

  DOI：10.1002/ardp.200400920

  日期：2005.4

  The synthesis of 4‐[3‐(substituted phenyl)‐2‐oxo‐5‐oxazolidinyl]methoxybenzoic acids and their inhibitory effects on the biosynthesis of fatty acids and sterols is described. IC50 values in vitro were 10−6 and 10−5 M, respectively. Though the in vitro inhibitory activity of all these compounds toward sterol biosynthesis was inferior to that of pravastatin, several compounds had a stronger reducing

  描述了 4-[3-(取代苯基)-2-氧代-5-恶唑烷基]甲氧基苯甲酸的合成及其对脂肪酸和甾醇生物合成的抑制作用。体外IC50值分别为10-6和10-5M。尽管所有这些化合物对甾醇生物合成的体外抑制活性不如普伐他汀，但有几种化合物在 Sprague-Dawley (SD) 大鼠中对胆固醇 (TC) 和甘油三酯 (TG) 的降低作用比普伐他汀更强和苯扎贝特。强效化合物以高浓度存在于大鼠肝脏中。制备了有效外消旋化合物（4-[3-（4-溴-2-氟苯基）-2-氧代-5-恶唑烷基]甲氧基苯甲酸）的对映体，并在体内和体外检测了它们的活性。在体内，每种对映异构体都比外消旋化合物具有更高的活性。
• Oxazolidine derivatives and pharmaceutically acceptable salts thereof
  申请人：Taiho Pharmaceutical Co., Ltd.

  公开号：US05480899A1

  公开（公告）日：1996-01-02

  An oxazolidine derivative represented by the formula (I) ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are H, optionally halogenated alkyl, optionally halogenated alkoxy, OH, halo, NO.sub.2, amino optionally having acetyl or alkyl, COOH, alkoxycarbonyl, CN, alkanoyl, 2-oxazolyl, or R.sup.1 and R.sup.2 may be combined with each other to represent --(CH.sub.2).sub.p -- or --O(CH.sub.2).sub.q O-- (p is 3-5, q is 1-3) to form a ring, m and n are each 0 or 1, R.sup.4 and R.sup.5 are H or alkyl, X is C or N, Y is CH.sub.2 OH, CHO or COOR.sup.6 (R.sup.6 is alkyl, benzyl or H), A is alkylene, carbonyl or sulfonyl, B is alkylene, E is alkylene which may be substituted with halo or is alkenylene, Z is O or S, except for a compound wherein n is 0, m is 1 and Y is CH.sub.2 OH, and except for a compound wherein n is 0, Y is COOR.sup.6 (R.sup.6 is alkyl), a salt thereof, a process for its preparation, anti-hyperlipidemic composition containing the derivative as an active ingredient and a method for treating hyperlipidemia comprising administering the derivative.

  一种由式(I)表示的噁唑啉衍生物 ##STR1## 其中，R.sup.1，R.sup.2和R.sup.3为H，可选卤代烷基，可选卤代烷氧基，OH，卤，NO.sub.2，氨基，可选择乙酰或烷基，COOH，烷氧羰基，CN，酰基，2-噁唑烷基，或R.sup.1和R.sup.2可以结合在一起表示为--(CH.sub.2).sub.p--或--O(CH.sub.2).sub.q O--(p为3-5，q为1-3)形成环，m和n分别为0或1，R.sup.4和R.sup.5为H或烷基，X为C或N，Y为CH.sub.2 OH，CHO或COOR.sup.6（R.sup.6为烷基，苄基或H），A为烷基，羰基或磺酰基，B为烷基，E为可以用卤代取代的烷基或烯基烷基，Z为O或S，但n为0，m为1且Y为CH.sub.2 OH的化合物除外，以及n为0，Y为COOR.sup.6（R.sup.6为烷基）的化合物除外，其盐，其制备方法，含有该衍生物作为活性成分的抗高脂血症组合物和治疗高脂血症的方法。
• 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.
• 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.