2,3-dideuterio-3-(3,4-dihydroxyphenyl)propionic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2,3-dideuterio-3-(3,4-dihydroxyphenyl)propionic acid
• 英文别名: 2,3-Dideuterio-3-(3,4-dihydroxyphenyl)propanoic acid；2,3-dideuterio-3-(3,4-dihydroxyphenyl)propanoic acid
• 化学式: C₉H₁₀O₄
• 分子量: 184.16
• InChiKey: DZAUWHJDUNRCTF-XRIVEGAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  TRANS-咖啡酸 在 samarium diiodide 、 重水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以73%的产率得到2,3-dideuterio-3-(3,4-dihydroxyphenyl)propionic acid
  参考文献：
  名称：

  Synthesis of Different Deuterated Carboxylic Acids from Unsaturated Acids Promoted by Samarium Diiodide and D2O

  摘要：

  An easy, and rapid reduction of the C=C bond of alpha,beta-unsaturated acids by means of samarium diiodide in the presence of D2O provides an efficient method for synthesizing 2,3-dideuterio acids. Starting from alka-2,4-dienoic acids, (E)-alpha,delta-dideuterio-betagamma-unsaturated acids are obtained, the new C=C bond being generated with complete diastereoselectivity. When H2O is used instead of D2O, saturated carboxylic acids and (E)-beta,gamma-unsaturated acids are isolated. A mechanism to explain each synthesis has been proposed.

  DOI：

  10.1002/1521-3765(20021004)8:19<4493::aid-chem4493>3.0.co;2-u

文献信息

• EP1991522A2
  申请人：——

  公开号：EP1991522A2

  公开（公告）日：2008-11-19
• COMPOSITION COMPRISING A DOPAMINE AGONIST AND AN L-DOPA DERIVATIVE FOR TREATING PARKINSON'S DISEASE
  申请人：ratiopharm GmbH

  公开号：EP3116477A2

  公开（公告）日：2017-01-18
• [EN] DEUTERATED CATECHOLAMINE DERIVATIVES AND MEDICAMENTS COMPRISING SAID COMPOUNDS<br/>[FR] DERIVES DE CATECHOLAMINE DEUTERIES ET MEDICAMENTS COMPRENANT DE TELS COMPOSES
  申请人：BIRDS PHARMA GMBH BEROLINA INN

  公开号：WO2007093450A2

  公开（公告）日：2007-08-23

  [EN] The present invention concerns deuterated catecholamine derivatives as well as pharmaceuticals containing these compounds. In addition, the invention concerns the use of deuterated catecholamine derivatives as well as physiologically acceptable salts thereof, and also pharmaceutical compositions, which contain these compounds, also in combination with enzyme inhibitors, for the treatment of dopamine deficiency diseases or diseases which are based on disrupted tyrosine transport or disrupted tyrosine decarboxylase, as well as other disorders.
  [FR] La présente invention concerne des dérivés de catécholamine deutériés ainsi que des compositions pharmaceutiques contenant ces composés. Par ailleurs, l'invention concerne l'utilisation de dérivés de catécholamine deutériés ainsi que des sels physiologiquement acceptables dérivés, et aussi des compositions pharmaceutiques qui contiennent ces composés, aussi en combinaison avec des inhibiteurs d'enzymes, pour le traitement de maladies de déficience en dopamine, ou de maladies basées sur le transport interrompu de la tyrosine ou d'une décarboxylase interrompue de tyrosine, ainsi que d'autres affections.
• [EN] PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OF PARKINSON'S DISEASE<br/>[FR] COMPOSITION PHARMACEUTIQUE POUR LE TRAITEMENT DE LA MALADIE DE PARKINSON
  申请人：IMPHAR AG

  公开号：WO2015136003A2

  公开（公告）日：2015-09-17

  Disclosed is a pharmaceutical composition comprising i) a dopamine agonist and ii) a L-DOPA derivative in combination in form of a liquid preparation. The pharmaceutical composition is used for the treatment of Parkinson's disease, restless leg syndrome, dystonia, for inhibiting prolactin secretion, for stimulating the release of growth hormones, for the treatment of neurological symptoms of chronic manganese intoxication, oamyotrophic lateral sclerosis, and multiple system atrophy.
• Synthesis of Different Deuterated Carboxylic Acids from Unsaturated Acids Promoted by Samarium Diiodide and D2O
  作者：José M. Concellón、Humberto Rodríguez-Solla

  DOI：10.1002/1521-3765(20021004)8:19<4493::aid-chem4493>3.0.co;2-u

  日期：2002.10.4

  An easy, and rapid reduction of the C=C bond of alpha,beta-unsaturated acids by means of samarium diiodide in the presence of D2O provides an efficient method for synthesizing 2,3-dideuterio acids. Starting from alka-2,4-dienoic acids, (E)-alpha,delta-dideuterio-betagamma-unsaturated acids are obtained, the new C=C bond being generated with complete diastereoselectivity. When H2O is used instead of D2O, saturated carboxylic acids and (E)-beta,gamma-unsaturated acids are isolated. A mechanism to explain each synthesis has been proposed.