3,4-methylenedioxyphenylalanine | 33522-63-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4-methylenedioxyphenylalanine
• 英文别名: 3,4-methanediyldioxy-phenylalanine；2-amino-3-benzo[1,3]dioxol-5-yl-propionic acid；3,4-methylenedioxy-DL-phenylalanine；3,4-Methylendioxy-DL-phenylalanin；2-Amino-3-benzo[1,3]dioxol-5-yl-propionsaeure；3-<3,4-Methylendioxy-phenyl>-DL-alanin；2-azaniumyl-3-(1,3-benzodioxol-5-yl)propanoate
• CAS: 33522-63-3
• 化学式: C₁₀H₁₁NO₄
• mdl: MFCD00666081
• 分子量: 209.202
• InChiKey: XHBLRJRZRFZSGW-UHFFFAOYSA-N

物化性质

• 熔点：
  238 °C
• 沸点：
  381.1±30.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-methylenedioxyphenylalanine 在 氯化亚砜 、 氨 作用下， 以 甲醇 为溶剂， 反应 111.0h， 生成 2-amino-3-(1,3-benzodioxol-5-yl)propanamide
  参考文献：
  名称：

  Brunner; Kroiss; Schmidt, European Journal of Medicinal Chemistry, 1986, vol. 21, # 4, p. 333 - 338

  摘要：

  DOI：
• 作为产物：
  描述：

  胡椒基氯 在 盐酸 、 乙醇 、 sodium ethanolate 、 钯 作用下， 生成 3,4-methylenedioxyphenylalanine
  参考文献：
  名称：

  3,4-二羟基苯丙氨酸（多巴）的新合成。

  摘要：

  DOI：

  10.1021/ja01182a079

文献信息

• Single-Biocatalyst Synthesis of Enantiopure<scp>d</scp>-Arylalanines Exploiting an Engineered<scp>d</scp>-Amino Acid Dehydrogenase
  作者：Fabio Parmeggiani、Syed T. Ahmed、Matthew P. Thompson、Nicholas J. Weise、James L. Galman、Deepankar Gahloth、Mark S. Dunstan、David Leys、Nicholas J. Turner

  DOI：10.1002/adsc.201600682

  日期：2016.10.20

  A practical and efficient biocatalytic synthesis of aromatic d‐amino acids has been developed, based on the reductive amination of the corresponding α‐keto acids via a recombinant whole cell system composed of an engineered dehydrogenase and cofactor recycling apparatus. The reaction was shown to give excellent enantioselectivity (≥98%) and good yields at the preparative scale across a broad range

  基于相应的α-酮酸通过由工程脱氢酶和辅因子回收装置组成的重组全细胞系统的还原胺化反应，已开发出一种实用，有效的芳香族d-氨基酸生物催化合成方法。结果表明，在制备规模上，该反应在多种底物上均具有出色的对映选择性（≥98％）和良好的收率。另外，解析了变体酶的结构以使观察到的反应速率合理化。工程化的全细胞催化剂还通过与对映体互补脱氨酶结合使用，来介导外消旋混合物和更便宜的l-氨基酸产生的d-苯丙氨酸衍生物。
• Studies on 1-Azabicyclo Compounds. XV. Oxidation of 1, 3, 4, 6, 11, 11a-Hexahydro-2H-pyrazino [1, 2-b] isoquinolin-1-one Derivatives with Mercuric Acetate, and Their Conversion into 1, 2, 3, 4, 5, 6, 7, 8-Octahydro-2-methyl-2, 5-benzodiazecine and Related Compounds
  作者：HIDEO KATO、EIICHI KOSHINAKA、YOSHIO ARATA、MIYOJI HANAOKA

  DOI：10.1248/cpb.21.2039

  日期：——

  Oxidation of hexahydro-2H-pyrazino [1, 2-b] isoquinolin-1-one (Ia) with mercuric acetate gave the α-aminocarbinol (II), which was characterized as the quaternary ammonium bromide (III). Mercuric acetate oxidation of the diamine (VII), however, afforded the lactam (VIII). Treatment of the methiodides (XIIa, XIIb, and XIIc) with lithium in liquid ammonia yielded the piperazinones (XIIIa, XIIIb, and XIIIc), respectively. On the other hand, reduction of the methiodides (XIIa, XIIb, and XIIc) with sodium amalgam furnished selectively the ten-membered aminolactams (XVIa, XVIb, and XVIc), respectively, in fair yields, which were converted to the corresponding ten-membered diamines (XVIIa, XVIIb, and XVIIc).

  六氢-2H-吡嗪并[1, 2-b]异喹啉-1-酮（Ia）与醋酸汞的氧化反应生成了α-氨基醇（II），该化合物被表征为季铵溴化物（III）。然而，二胺（VII）与醋酸汞的氧化反应则生成了内酰胺（VIII）。将甲碘化物（XIIa、XIIb和XIIc）与锂在液氨中反应，分别得到了哌嗪酮（XIIIa、XIIIb和XIIIc）。另一方面，用钠汞合金还原甲碘化物（XIIa、XIIb和XIIc），选择性地得到了十元氨基内酰胺（XVIa、XVIb和XVIc），产率尚可，随后这些化合物被转化为相应的十元二胺（XVIIa、XVIIb和XVIIc）。
• 2-Aminooxazolines as TAAR1 ligands
  申请人：Galley Guido

  公开号：US20080261920A1

  公开（公告）日：2008-10-23

  The invention relates to compounds of formula I wherein X, Y, R 1 , R 2 , and n are as defined herein or to a pharmaceutically suitable acid addition salt thereof. The invention also relates to pharmaceutical compositions containing such compounds and methods for the treatment of diseases related to the biological function of the trace amine associated receptors, which diseases include depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders, schizophrenia, neurological diseases, Parkinson's disease, neurodegenerative disorders, Alzheimer's disease, epilepsy, migraine, substance abuse and metabolic disorders, eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  本发明涉及化合物I的公式，其中X，Y，R1，R2和n如本文所定义，或其药学上适宜的酸加盐。本发明还涉及含有这种化合物的制药组合物和治疗与微量胺相关受体的生物学功能相关的疾病的方法，这些疾病包括抑郁症、焦虑症、双相情感障碍、注意力缺陷多动障碍、压力相关障碍、精神障碍、精神分裂症、神经系统疾病、帕金森病、神经退行性疾病、阿尔茨海默病、癫痫、偏头痛、物质滥用和代谢性疾病、进食障碍、糖尿病、糖尿病并发症、肥胖症、血脂异常、能量消耗和吸收障碍、体温稳态障碍和功能障碍、睡眠和昼夜节律障碍以及心血管疾病。
• 2-AMINOOXAZOLINES AS TAAR1 LIGANDS
  申请人：Galley Guido

  公开号：US20100120864A1

  公开（公告）日：2010-05-13

  The invention relates to compounds of formula I wherein X, Y, R 1 , R 2 , and n are as defined herein or to a pharmaceutically suitable acid addition salt thereof. The invention also relates to pharmaceutical compositions containing such compounds and methods for the treatment of diseases related to the biological function of the trace amine associated receptors, which diseases include depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders, schizophrenia, neurological diseases, Parkinson's disease, neurodegenerative disorders, Alzheimer's disease, epilepsy, migraine, substance abuse and metabolic disorders, eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  本发明涉及式I的化合物，其中X，Y，R1，R2和n如本文所定义，或其药学适宜的酸加盐。本发明还涉及含有此类化合物的制药组合物，以及用于治疗与微量胺相关受体的生物学功能相关的疾病的方法，这些疾病包括抑郁症，焦虑症，双相情感障碍，注意力缺陷多动障碍，应激相关障碍，精神疾病，精神分裂症，神经疾病，帕金森病，神经退行性疾病，阿尔茨海默病，癫痫，偏头痛，物质滥用和代谢性疾病，进食障碍，糖尿病，糖尿病并发症，肥胖症，血脂异常，能量消耗和吸收障碍，体温稳态障碍和功能障碍，睡眠和生物钟节律障碍以及心血管疾病。
• Process for producing threo-3-(3,4-dihydroxyphenyl)serine
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0084928A1

  公开（公告）日：1983-08-03

  A process for producing an optically active threo-3-(3,4--dihydroxyphenyl)serine represented by the formula which is useful as a remedy for peripheral orthostatic hypotension or as an antidepressant, which process comprises (A) treating threo-3-(3,4-methylenedioxyphenyl)serine or an N-carbobenzoxy derivative thereof represented by the formula wherein A represents a hydrogen atom or a carbobenzoxy group, with a Lewis acid to form threo-3(3,4-dihy- droxyphenyllserine or an N-carbobenzoxy derivative thereof represented by the formula wherein A is a defined above, and, if A is a carbobenzoxy group, catalytically reducing the resulting compound of formula (2); or (B) allowing the crystals of an optically active threo-3-(3,4--dihydroxyphenyl)serine to be present in a supersaturated solution of racemic threo-3-(3,4-dihydroxyphenyi)serine, and allowing the same optically active threo-3-(3,4-dihydroxyphenyl)serine as said crystals to crystallize preferentially out of said supersaturated solution; a racemic or optically active threo-N-carbobenzoxy-3-(3,4-methytenedioxyphenyl)serine represented by the formula which is a novel compound useful as an intermediate in the above synthesis; and a process for producing said novel com pound.

  一种生产光学活性苏-3-(3,4-二羟基苯基)丝氨酸的工艺，其化学式为 该工艺包括 (A) 用如下式子表示的硫代-3-(3,4-亚甲基二氧苯基)丝氨酸或其 N-羰基苯氧基衍生物进行处理 其中 A 代表氢原子或羰基苯氧基，用路易斯酸形成由式表示的硫代-3-(3,4-二亚甲基二氧苯基)丝氨酸或其 N-羰基苯氧基衍生物； (B) 用路易斯酸处理由式表示的硫代-3-(3,4-二亚甲基二氧苯基)丝氨酸或其 N-羰基苯氧基衍生物。 其中 A 是上文所定义的，如果 A 是羰基苯氧基，则催化还原生成的式 (2) 化合物；或 (B) 使外消旋苏-3-(3,4-二羟基苯基)丝氨酸的过饱和溶液中存在光学活性苏-3-(3,4-二羟基苯基)丝氨酸的晶体，并使与所述晶体相同的光学活性苏-3-(3,4-二羟基苯基)丝氨酸优先从所述过饱和溶液中结晶出来；一种外消旋或具有光学活性的硫代-N-苄氧基-3-(3,4-甲基tenedioxyphenyl)丝氨酸，其化学式为 这是一种新型化合物，可用作上述合成的中间体；以及生产上述新型化合物的工艺。