乙基3-(1,3-苯并二氧戊环-5-基)-2-甲酰基丙酸酯 | 72716-70-2

• 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
• 中文名称: 乙基3-(1,3-苯并二氧戊环-5-基)-2-甲酰基丙酸酯
• 中文别名: 4-氯-3-[4-[[5-氯-2-(2-氯苯氧基)苯基]偶氮]-4,5-二氢-3-甲基-5-羰基-1H-吡唑-1-基]苯磺化钠
• 英文名称: ethyl 2-formyl-3-(3,4-methylenedioxyphenyl)-propionate
• 英文别名: Ethyl alpha-formyl-1,3-benzodioxole-5-propanoate；ethyl 2-(1,3-benzodioxol-5-ylmethyl)-3-oxopropanoate
• CAS: 72716-70-2
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: MPWATBGBEKGSJA-UHFFFAOYSA-N

物化性质

• 沸点：
  354.6±30.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  乙基3-(1,3-苯并二氧戊环-5-基)-2-甲酰基丙酸酯 在 recombinant Escherichiacoli HB 101 (pTSBG₁) Accession No_. FERM BP-6898 作用下， 反应 24.0h， 生成 Ethyl (S)-2-hydroxymethyl-3-(3,4-methylenedioxyphenyl)propionate
  参考文献：
  名称：

  PROCESSES FOR PRODUCING OPTICALLY ACTIVE 2-THIOMETHYL-3-PHENYLPROPIONIC ACID DERIVATIVE AND FOR PRODUCING INTERMEDIATE THEREFOR

  摘要：

  本发明提供了一种简单生产光学活性2-硫甲基-3-苯丙酸衍生物的方法，该衍生物可作为药物中间体，使用廉价原料。通过酶的不对称还原反应，可以相对容易地获得光学活性2-羟甲基-3-苯丙酸酯衍生物，然后将其环化为光学活性β-内酯衍生物，再与硫化合物反应，高产率地生产光学活性2-硫甲基-3-苯丙酸衍生物。

  公开号：

  EP1577310A1
• 作为产物：
  描述：

  3-苯并[1,3]二氧杂环戊烯-5-基-丙酸乙酯 、 甲酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 32.0h， 生成 乙基3-(1,3-苯并二氧戊环-5-基)-2-甲酰基丙酸酯
  参考文献：
  名称：

  EP1568679

  摘要：

  公开号：

文献信息

• Processes for producing optically active 2-thiomethyl-3-phenylpropionic acid derivative and for producing intermediate therefor
  申请人：Ohishi Takahiro

  公开号：US20060089503A1

  公开（公告）日：2006-04-27

  The present invention provides a process for simply producing an optically active 2-thiomethyl-3-phenylpropionic acid derivative useful as an intermediate for medicines from inexpensive raw materials. An optically active 2-hydroxymethyl-3-phenylpropionic acid ester derivative which can be relatively easily obtained by asymmetric reduction reaction with an enzyme is cyclized to an optically active P-lactone derivative which is then reacted with a sulfur compound to produce an optically active 2-thiomethyl-3-phenylpropionic acid derivative in high yield.

  本发明提供一种从廉价原料简单制备用于药物中间体的光学活性2-硫代甲基-3-苯丙酸衍生物的方法。通过酶的不对称还原反应可以相对容易地得到一种光学活性的2-羟甲基-3-苯丙酸酯衍生物，该衍生物被环化成为一种光学活性的P-内酯衍生物，然后与硫化合物反应，高产率地产生一种光学活性的2-硫代甲基-3-苯丙酸衍生物。
• Process for producing optically active 3-hydroxypropionic ester derivative
  申请人：Taoka Naoaki

  公开号：US20060166342A1

  公开（公告）日：2006-07-27

  The present invention is to provide a process for simply producing an optically active 3-hydroxypropionic ester derivative useful as a medicament intermediate from an inexpensive material. More specifically, the present invention is directed to a process for producing an optically active 3-hydroxypropionic ester derivative comprising reacting an acetic ester derivative available at low cost with abase and a formic ester, thereby converting the acetic ester derivative into a 2-formylacetic ester derivative, and thereafter, stereospecifically reducing the formyl group of the derivative by use of an enzymatic source capable of stereoselectively reducing the formyl group of the derivative.

  本发明提供了一种简单制备光学活性的3-羟基丙酸酯衍生物，该衍生物可用作药物中间体，从廉价原料中制备。更具体地，本发明涉及一种制备光学活性的3-羟基丙酸酯衍生物的方法，包括将一种低成本的乙酸酯衍生物与碱和甲酸酯反应，从而将乙酸酯衍生物转化为2-甲酰乙酸酯衍生物，然后使用能够立体选择性还原该衍生物的酶源，立体特异性地还原衍生物的甲酰基。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE 3-HYDROXYPROPIONIC ESTER DERIVATIVE
  申请人：TAOKA Naoaki

  公开号：US20100016627A1

  公开（公告）日：2010-01-21

  A 2-formylacetic ester derivative represented by the general formula (5) is provided: where R 4 represents an alkyl group having 2 to 6 carbon atoms; R 5 represents an alkyl group having 1 to 10 carbon atoms; and X represents H, Li, Na or K.

  提供一种由一般式(5)表示的2-甲酰基乙酸酯衍生物：其中R4代表具有2至6个碳原子的烷基；R5代表具有1至10个碳原子的烷基；X代表H、Li、Na或K。
• Pyrimidinone derivatives, processes for preparing them and pharmaceutical compositions containing them
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0013071A1

  公开（公告）日：1980-07-09

  The invention provides new histamine H2- antagonist compounds of Structure 1 in which R' is hydrogen, lower alkyl, lower alkoxy, hydroxy, halogen, trifluoromethyl, nitro, amino, lower alkylamino, lower alkanoylamino, di(lower alkyl)amino or cyano; R2 is in the 3-, 4- or 5- position and is hydrogen, or R2 is lower alkyl substituted by amino, lower alkylamino, di(lower alkyl)amino, N-piperidino or N-pyrollidino, or R2 is ethoxy or propoxy w-substituted by amino, lower alkylamino, di(lower alkyl)amino, N-piperidino or N-pyrollidino; Y is methylene or oxygen and X is methylene or sulphur provided that one or two of the groups X and Y is methylene; Z is hydrogen or lower alkyl; A is C1-C5 alkylene or-(CH2)pW-(CH2)q-where W is oxygen or sulphur and p and q are such that their sum is from 1 to4, and B is hydrogen, methyl, C3-C6 cycloalkyl, a heteroaryl group optionally substituted by one or more of the groups lower alkyl, lower alkoxy, halo, hydroxy and amino, or B is a naphthyl, 6-(2,3-dihydro-1,4-benzodioxinyl), a 4- or 5-(1,3-benzodioxolyl) group, or a phenyl group optionally substituted with one or more lower alkyl, lower alkoxy, halogen, aryl(lower alkoxy), hydroxy, lower alkoxy-lower alkoxy, trifluoromethyl, di(lower alkyl)amino, phenoxy, halophenoxy, lower alkoxyphenoxy, phenyl, halophenyl or lower alkoxyphenyl groups and pharmaceutical compositions containing them. A compound of Structure 1 can be prepared by reacting a compound of Structure 3 in which Q is nitroamino, loweralkylthio, benzylthio or halogen with an amine of Structure 2, in which R3 is in the 3-, 4- or 5p position and is hydrogen, lower alkyl substituted by a group R4, or is R4CH2CH2O-or R4CH2CH2CH2O-, where R' is di(lower alkyl)amino, N-piperidino, N-pyrrollidino, a protected amino group or a protected lower alkylamino group, and where necessary any amino-protecting group present in the substituent R3 is removed.

  本发明提供了结构 1 的新型组胺 H2- 拮抗剂化合物 其中R'是氢、低级烷基、低级烷氧基、羟基、卤素、三氟甲基、硝基、氨基、低级烷基氨基、低级烷酰氨基、二（低级烷基）氨基或氰基；R2 位于 3-、4-或 5-位且为氢，或 R2 为被氨基、低级烷基氨基、二（低级烷基）氨基、N-哌啶基或 N-吡咯烷基取代的低级烷基，或 R2 为被氨基、低级烷基氨基、二（低级烷基）氨基、N-哌啶基或 N-吡咯烷基取代的乙氧基或丙氧基；Y 为亚甲基或氧，X 为亚甲基或硫，条件是 X 和 Y 中的一个或两个基团为亚甲基；Z 为氢或低级烷基；A是C1-C5亚烷基或-(CH2)pW-(CH2)q-其中W是氧或硫，p和q的和为1至4，B是氢、甲基、C3-C6环烷基、任选被一个或多个基团低级烷基、低级烷氧基、卤代、羟基和氨基取代的杂芳基，或者B是萘基、6-(2,3-二氢-1,4-苯并二噁烷基)、4-或5-(1、3-苯并二恶茂基）基团，或任选被一个或多个低级烷基、低级烷氧基、卤素、芳基（低级烷氧基）、羟基、低级烷氧基-低级烷氧基、三氟甲基、二（低级烷基）氨基、苯氧基、卤代苯氧基、低级烷氧基苯氧基、苯基、卤代苯基或低级烷氧基苯基基团取代的苯基基团以及含有它们的药物组合物。结构 1 的化合物可通过结构 3 的化合物（其中 Q 为硝基氨基、低级烷硫基、苄硫基或卤素） 与结构 2 的胺反应制备，其中 R3 位于 3-、4-或 5p 位，是氢、被基团 R4 取代的低级烷基或 R4CH2CH2O- 或 R4CH2CH2CH2O-，其中 R' 是二（低级烷基）氨基、N-哌啶基、N-吡咯烷基、受保护的氨基或受保护的低级烷基氨基，必要时去除取代基 R3 中存在的任何氨基保护基。
• A process for preparing pyrimidones
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0024873A1

  公开（公告）日：1981-03-11

  A process is disclosed for preparing compounds of formula (1) : and acid addition salts thereof where Het is an optionally substituted 5-or6- membered fully unsaturated nitrogen containing heterocyclic group where the substituents (which can be the same or different) are one or more C1-4 alkyl, trifluoromethyl, halogen, hydroxy, C1-4 alkoxy or amino groups; n is 2 or 3; Z is hydrogen or C1-4 alkyl; A is C1-5 alkylene optionally interrupted with oxygen or sulphur and B is hydrogen, methyl, C3-6 cycloalkyl, an optionally substituted heteroaryl group where the substituents (which can be the same or different) are one or more C1-4 alkyl, C1-4 alkoxy or hydroxy groups; or B is a naphthyl, 5- or 6-(2,3-dihydro-1, 4-benzodioxinyl) or a 4- or 5-(1,3-benzodioxolyl) group or an optionally substituted phenyl group where the substituents (which can be the same or different) are one or more C1-4 alkyl, C1-4 alkoxy, halogen, aryl-(C1-4 alkoxy), hydroxy, C1-4 alkoxy-C1-4 alkoxy, trifluoromethyl, di(C1-4 alkyl) amino, phenoxy, halophenyl, or C1-4 alkoxyphenyl groups which comprises reacting a compound of formula (4) :- or an acid addition salt thereof where Het is as defined with reference to formula 11) provided that any substituents which interfere with the reaction are protected and L is a group displacable with thiol with a compound of formula (3) :- or an acid addition salt thereof where n, Z, A and B are as defined with reference to formula (1) provided that any phenolic hydroxy groups within B are optionally protected, and thereafter removing any protecting groups.

  本发明公开了一种制备式 (1) ： 及其酸加成盐 其中 Het 是任选取代的 5 或 6 位元完全不饱和含氮杂环基团，取代基（可以相同或不同）是一个或多个 C1-4 烷基、三氟甲基、卤素、羟基、C1-4 烷氧基或氨基；n 是 2 或 3；Z 是氢或 C1-4 烷基；A 是任选用氧或硫间断的 C1-5 亚烷基，B 是氢、甲基、C3-6 环烷基、任选取代的杂芳基，其中取代基（可以相同或不同）是一个或多个 C1-4 烷基、C1-4 烷氧基或羟基；或 B 是萘基、5-或 6-(2,3-二氢-1,4-苯并二氧杂环戊基)或 4-或 5-(1,3-苯并二氧杂环戊基)基团或任选取代的苯基，其中取代基（可以相同或不同）是一个或多个 C1-4 烷基、C1-4 烷氧基、卤素或羟基、- 或其酸加成盐，其中 Het 如参照式 11 所定义），条件是任何干扰反应的取代基均被保护，且 L 为可与硫醇置换的基团，与式 (3) 化合物：- 反应 或其酸加成盐 其中 n、Z、A 和 B 如参照式（1）所定义，但 B 中的任何酚羟基可选择被保护，然后去除任何保护基团。