(R)-(-)-2-(3,4-methylenedioxyphenyl)-2-hydroxyacetic acid | 32345-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (R)-(-)-2-(3,4-methylenedioxyphenyl)-2-hydroxyacetic acid
• 英文别名: 3,4-(methylenedioxy)mandelic acid；(R)-benzo[1,3]dioxol-5-yl-hydroxy-acetic acid；(R)-3,4-methylenedioxymandelic acid；(2R)-2-(1,3-benzodioxol-5-yl)-2-hydroxyacetic acid
• CAS: 32345-76-9
• 化学式: C₉H₈O₅
• 分子量: 196.16
• InChiKey: CLUJFRCEPFNVHW-MRVPVSSYSA-N

物化性质

• 沸点：
  403.5±45.0 °C(Predicted)
• 密度：
  1.553±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-(3,4-methylenedioxyphenyl)-2-hydroxyacetic acid 生成 (6R)-3-acetoxymethyl-7t-((R)-2-benzo[1,3]dioxol-5-yl-2-hydroxy-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; triethylamine salt
  参考文献：
  名称：

  半合成头孢菌素。7-mandelamido-3-cephem-4-羧酸的合成及其构效关系。

  摘要：

  DOI：

  10.1021/jm00247a008
• 作为产物：
  描述：

  (R)-Acetoxy-benzo[1,3]dioxol-5-yl-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 生成 (R)-(-)-2-(3,4-methylenedioxyphenyl)-2-hydroxyacetic acid
  参考文献：
  名称：

  GUY, ALAIN;LEMOR, ALAIN;IMBERT, DOMINIQUE;LEMAIRE, MARC, TETRAHEDRON LETT., 30,(1989) N, C. 327-330

  摘要：

  DOI：

文献信息

• Convergency and Divergency as Strategic Elements in Total Synthesis:  The Total Synthesis of (−)-Drupacine and the Formal Total Synthesis of (±)-Cephalotaxine, (−)-Cephalotaxine, and (+)-Cephalotaxine
  作者：Qi Liu、Eric M. Ferreira、Brian M. Stoltz

  DOI：10.1021/jo0710883

  日期：2007.9.1

  A concise route toward the syntheses of (−)-drupacine and (+)- and (−)-cephalotaxine has been developed. The syntheses rely on Pd(II)-catalyzed aerobic oxidative heterocyclization chemistry, which was employed to rapidly construct an important spirocyclic amine intermediate. A dynamic β-elimination/conjugate addition process was strategically applied to complete the first asymmetric total synthesis

  已经开发出一种简明的合成（-）-杜帕卡因和（+）-和（-）-头孢他辛的方法。合成依赖于Pd（II）催化的好氧氧化杂环化学，该化学可用于快速构建重要的螺环胺中间体。策略性地应用了动态β消除/共轭加成过程，以完成（-）-杜拉帕汀的首次不对称全合成。
• Optical Resolution by Preferential Crystallization of 2-(3,4-Carbonyldioxyphenyl)-2-(phthalimidooxy)acetic Acid, a Key Intermediate of Cephalosporin Antibiotic M-14659
  作者：Kimihiro Murakami、Masayuki Ohashi、Atsuo Matsunaga、Ichiro Yamamoto、Akira Tomiguchi、Hiroyuki Nohira

  DOI：10.1246/bcsj.65.3288

  日期：1992.12

  (±)-2-(3,4-Carbonyldioxyphenyl)-2-(phthalimidooxy)acetic acid [(±)-1] was efficiently resolved into a pair of optically active forms by preferential crystallization. Successive preferential crystallization of (±)-1 was experimented at 15 °C under stirring in acetone, and (+)- and (−)-1 with optical purity of 68–85% were obtained. The racemization of (−)-1 proceeded smoothly in the presence of triethylamine to give (±)-1 which was reusable for the preferential crystallization procedure. A potent antipseudomonal cephalosporin M-14659 (2) was prepared from (+)-1.

  (±)-2-(3,4-羧基二氧苯基)-2-(邻苯二甲酰胺氧基)乙酸[(±)-1]通过优先结晶高效分离为一对光学活性形式。在15°C下搅拌的条件下，在丙酮中对(±)-1进行了连续的优先结晶实验，得到了光学纯度为68–85%的(+)和(−)-1。(-)-1在三乙胺的存在下平稳地进行了外消旋化反应，生成了可重复用于优先结晶过程的(±)-1。一种有效的抗伪单胞菌头孢菌素M-14659(2)是从(+) -1制备而来的。
• NEW AMINO ACID DERIVATIVES
  申请人：AstraZeneca AB

  公开号：US20040087647A1

  公开（公告）日：2004-05-06

  There is provided amino acid derivatives of formula I, 1 wherein p, q, R 1 , R 2 , R 3 , R 4 , Y, n and B have meanings given in the description which are useful as competitive inhibitors of trypsin-like proteases, such as thrombin, and in particular in the treatment of conditions where inhibition of thrombin is required (e.g. thrombosis) or as anticoagulants.

  提供了公式I，其中p，q，R1，R2，R3，R4，Y，n和B具有在描述中给出的含义，这些衍生物可用作类似胰蛋白酶的竞争性抑制剂，如凝血酶，并特别用于治疗需要抑制凝血酶的情况（例如血栓形成）或作为抗凝剂。
• Amino acid derivatives
  申请人：Astra AB

  公开号：US20020042396A1

  公开（公告）日：2002-04-11

  There is provided amino acid derivatives of formula I, 1 wherein p, q, R 1 , R 2 , R 3 , R 4 , Y, n and B have meanings given in the description which are useful as competitive inhibitors of trypsin-like proteases, such as hirombin, and in particular in the treatment of conditions where inhibition of thrombin is required (e.g. thrombosis) or as anticoagulants.

  提供了公式I,1的氨基酸衍生物，其中p，q，R1，R2，R3，R4，Y，n和B的含义如描述中所示，可作为类似胰蛋白酶的竞争性抑制剂，例如hirombin，并且特别适用于需要抑制凝血酶的情况（例如血栓形成）或作为抗凝剂的治疗。
• Ester derivatives
  申请人：Ogino Yoshio

  公开号：US20050065211A1

  公开（公告）日：2005-03-24

  This invention relates to compounds which exhibit selective muscarinic M 3 receptor antagonism, have little side effects, are suitable for inhalation therapy and are useful as treating agents of respiratory system diseases, of the general formula (I); [in which A signifies a group expressed by a formula (a 0 ) or (b 0 ); Ar signifies optionally substituted aryl or heteroaryl; B 1 and B 2 signify aliphatic hydrocarbon; R 1 signifies fluorine-substituted cycloalkyl; R 2 , R 3 and R 4 signify lower alkyl, single bond or alkylene bonded to B 1 , or R 2 and R 3 are united to signify alkylene; R 5 and R 7 signify hydrogen, lower alkyl, or a single bond or alkylene bonded to B 2 ; R 6 signifies hydrogen, lower alkyl or a group expressed as —N(R 8 )R 9 ; and X − signifies an anion].

  本发明涉及具有选择性肌动蛋白M3受体拮抗作用、副作用小、适用于吸入治疗并且可用于呼吸系统疾病治疗的化合物，其通式为(I);[其中A表示由式(a0)或(b0)表示的基团；Ar表示可选取代的芳基或杂环芳基；B1和B2表示脂肪烃基；R1表示氟代环烷基；R2、R3和R4表示低碳基、单键或与B1结合的烷基，或者R2和R3结合表示烷基；R5和R7表示氢、低碳基或与B2结合的单键或烷基；R6表示氢、低碳基或表示为—N(R8)R9的基团；X-表示阴离子]。