3-chloroalpha-(((2-(3,4-dimethoxyphenyl)-1-methylethyl)amino)methyl)-benzenemethanol | 138908-48-2

• 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: 3-chloroalpha-(((2-(3,4-dimethoxyphenyl)-1-methylethyl)amino)methyl)-benzenemethanol
• 英文别名: 1-(3-chlorophenyl)-2-[[2-(3,4-dimethoxyphenyl)-1-methylethyl]amino]ethanol；N-[2-(3,4-dimethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine；N-[2-(3-chlorophenyl)-2-hydroxyeth-1-yl]-1-(3,4-dimethoxyphenyl)-prop-2-ylamine；[R-(R*,R*)]-1-(3-chlorophenyl)-2-[2-(3,4-dimethoxy-phenyl)-1-methyl-ethylamino]ethanol；3-Chloroalpha-(((2-(3,4-dimethoxyphenyl)-1-methylethyl)amino)methyl) benzenemethanol；1-(3-chlorophenyl)-2-[1-(3,4-dimethoxyphenyl)propan-2-ylamino]ethanol
• CAS: 138908-48-2
• 化学式: C₁₉H₂₄ClNO₃
• 分子量: 349.857
• InChiKey: OFQFWPQFYLFCTO-UHFFFAOYSA-N

物化性质

• 沸点：
  501.0±45.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloroalpha-(((2-(3,4-dimethoxyphenyl)-1-methylethyl)amino)methyl)-benzenemethanol 在 三溴化硼 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (R*,S*)-5-(3-chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone
  参考文献：
  名称：

  Method of increasing lean meat in edible animals

  摘要：

  本发明揭示了替代的1,3-苯并二氧苯并具有人类和其他动物的抗糖尿病和/或抗高血糖和/或抗肥胖特性。

  公开号：

  US05106867A1
• 作为产物：
  描述：

  3,4-二甲氧基苯丙酮 、 (1R)-2-氨基-1-(3-氯苯基)乙醇 以 二氯甲烷 为溶剂， 生成 3-chloroalpha-(((2-(3,4-dimethoxyphenyl)-1-methylethyl)amino)methyl)-benzenemethanol
  参考文献：
  名称：

  Secondary amines

  摘要：

  该公式（II）的化合物：##STR1##或其盐；其中R.sup.1为氢或甲基，R.sup.2为氢或甲基，R.sup.3为氢，C.sub.1-12直链或支链烷基，C.sub.3-10环烷基，苯基(C.sub.1-4)-烷基或苄基，可选择地被C.sub.1-4烷基，C.sub.1-4烷氧基或卤素取代；R.sup.4为氢，卤素，羟基，C.sub.1-4烷基或C.sub.1-4烷氧基，R.sup.5为氢或氟，R.sup.6为氢或氟，R.sup.7为卤素；n为1或2，具有抗肥胖和/或抗高血糖活性。

  公开号：

  US04622342A1

文献信息

• Optically active 1-phenyl-2-substituted propane derivatives and methods
  申请人：Daicel Chemical Industries, Ltd.

  公开号：US05508461A1

  公开（公告）日：1996-04-16

  An (S)-1-phenyl-2-substituted propane derivative shown by the following formula (I) ##STR1## wherein R.sup.1 and R.sup.2 represent a lower alkyl group, etc., or R.sup.1 and R.sup.2 may form together an alkylene group, etc.; R.sup.3, R.sup.4 and R.sup.5 represent a hydrogen atom, etc.; and X represents a hydroxyl group which may be protected with a protective group, or a halogen atom etc., can readily be produced (i) by permitting a microorganism belonging to the genus Torulaspora, the genus Candida, the genus Pichia or the like to act on a phenylacetone derivative and asymmetrically reducing the compound, or (ii) by sterically inverting an (R)-enantiomer. (R,R)-1-phenyl-2-[(2-phenyl-1-methylethyl)amino]ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (I). The ethanol derivative is useful as an anti-obesity agent and the like.

  公式（I）所示的一种（S）-1-苯基-2-取代丙烷衍生物，其中R.sup.1和R.sup.2代表较低的烷基基团等，或R.sup.1和R.sup.2可以共同形成烷基基团等；R.sup.3、R.sup.4和R.sup.5代表氢原子等；X代表可用保护基保护的羟基或卤原子等，可通过以下方法轻松制备：（i）使属于酵母属、念珠菌属、毛孢酵母属等的微生物作用于苯乙酮衍生物并对化合物进行不对称还原，或者（ii）通过立体上反转（R）-对映体。从公式（I）的化合物中可以轻松获得具有高光学纯度的（R，R）-1-苯基-2-[(2-苯基-1-甲基乙基)氨基]乙醇衍生物。这种乙醇衍生物可用作抗肥胖剂等。
• Substituted 5-(2-((2-aryl-2-hydroxyethyl)amino)propyl)-1,3-benzodioxoles
  申请人：American Cyanamid Company

  公开号：US05061727A1

  公开（公告）日：1991-10-29

  The present invention discloses substituted 1,3-benzodioxoles which possess anti-diabetic and/or anti-hyperglycemic and/or anti-obesity properties in humans and other animals.

  本发明揭示了替代的1,3-苯并二氧苯，其具有人类和其他动物中的抗糖尿病和/或抗高血糖和/或抗肥胖特性。
• Substituted 5-(2-(2-aryl-2-hydroxyethyl)-amino)propyl)-1,3-benzodioxoles
  申请人：American Cyanamid Company

  公开号：US05245053A1

  公开（公告）日：1993-09-14

  A process is disclosed for obtaining the R,R isomer of: ##STR1## wherein R.sub.1 and R.sub.2 may be one or more groups which may be the same or different and are selected from the group consisting of hydrogen, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, hydroxy, halogen, trifluoromethyl, carboxy, hydroxyalkyl, alkoxycarbonyl, C.sub.1 to C.sub.4 thioalkyl, sulfonyl and sulfinyl; X is a divalent radical consisting of ##STR2## wherein R' is hydrogen; R.sub.2 and R.sub.3 may be the same or different and are selected from the group consisting of hydrogen and C.sub.1 to C.sub.4 alkyl; R.sub.5 and R.sub.6 are selected from the group consisting of hydrogen, carboxy, alkoxycarbonyl, hydroxymethyl, --CH.sub.2 OCH.sub.2 COOR.sub.7 and --CH.sub.2 OCH.sub.2 CH.sub.2 OR.sub.7 where R.sub.7 is hydrogen or C.sub.1 to .sub.4 alkyl; except that R.sub.5 and R.sub.6 may not both be hydrogen; and the asterisks denote asymmetric carbon atoms; said process comprising the steps of: (a) reacting Mosher's acid with a compound of formula I to attach a group of the formula ##STR3## at the N-9 position of a mixture of (+) and (-) enantiomers of said compound to form a new pair of diastereoisomers; and (b) separating said new pair of diastereoisomers by HPLC and recovering the R,R isomer. The process is based on reacting Mosher's acid with the compound of formula I and thereafter using HPLC to separate the R,R isomer.

  本发明公开了一种获得R,R异构体的方法：##STR1## 其中，R1和R2可以是一个或多个基团，可以相同也可以不同，选择自氢、C.sub.1到C.sub.4烷基、C.sub.1到C.sub.4烷氧基、羟基、卤素、三氟甲基、羧基、羟基烷基、烷氧羰基、C.sub.1到C.sub.4硫代烷基、磺酰基和亚磺酰基的群；X是一个二价基团，由##STR2##组成，其中R'是氢；R2和R3可以相同也可以不同，选择自氢和C.sub.1到C.sub.4烷基；R5和R6选择自氢、羧基、烷氧羰基、羟甲基、--CH.sub.2 OCH.sub.2 COOR.sub.7和--CH.sub.2 OCH.sub.2 CH.sub.2 OR.sub.7，其中R.sub.7是氢或C.sub.1到C.sub.4烷基；但R.sub.5和R.sub.6不能同时为氢；星号表示不对称碳原子；该方法包括以下步骤：(a)将Mosher酸与式I化合物反应，将##STR3##式的基团附加到该化合物的(+)-和(-)-对映体混合物的N-9位置，形成一对新的对映异构体；(b)通过HPLC分离所述新的对映异构体并回收R,R异构体。该方法基于将Mosher酸与式I化合物反应，然后使用HPLC分离R,R异构体。
• Process of asymmetrically reducing 1-phenyl-2-oxo-propane derivatives
  申请人：Daicel Chemical Industries, Limited

  公开号：US05679557A1

  公开（公告）日：1997-10-21

  An (S)-1-phenyl-2-substituted propane derivative shown by the following formula (I) ##STR1## wherein R.sup.1 and R.sup.2 represent a lower alkyl group, etc., or R.sup.1 and R.sup.2 may form together an alkylene group, etc.; R.sup.3, R.sup.4 and R.sup.5 represent a hydrogen atom, etc.; and X represents a hydroxyl group which may be protected with a protective group, or a halogen atom etc., can readily be produced (i) by permitting a microorganism belonging to the genus Torulaspora, the genus Candida, the genus Pichia or the like to act on a phenylacetone derivative and asymmetrically reducing the compound, or (ii) by sterically inverting an (R)-enantiomer. (R,R)-1-phenyl-2-\x9b(2-phenyl-1-methylethyl)amino!ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (I). The ethanol derivative is useful as an anti-obesity agent and the like.

  以下式子(I)所示的(S)-1-苯基-2-取代丙烷衍生物：##STR1## 其中，R.sup.1和R.sup.2代表低碳链基等，或R.sup.1和R.sup.2可以共同形成一个亚烷基等；R.sup.3，R.sup.4和R.sup.5代表氢原子等；X代表一个羟基，该羟基可以用保护基保护，或卤原子等，可以通过(i)让属于Torulaspora属，Candida属，Pichia属或类似菌属的微生物作用于苯乙酮衍生物并不对称还原化合物，或(ii)通过立体上反转(R)-对映体来轻松制备。可以从式(I)的化合物中轻松获得具有高光学纯度的(R,R)-1-苯基-2-\x9b(2-苯基-1-甲基乙基)氨基!乙醇衍生物。该乙醇衍生物可用作抗肥胖剂等。
• Optically active 1-phenyl-2-substituted propane derivatives and methods of producing the same
  申请人：Daicel Chemical Industries, Ltd.

  公开号：US06248573B1

  公开（公告）日：2001-06-19

  An (S)-1-phenyl-2-substituted propane derivative shown by the following formula (I) wherein R1 and R2 represent a lower alkyl group, etc., or R1 and R2 may form together an alkylene group, etc.; R3, R4 and R5 represent a hydrogen atom, etc.; and X represents a hydroxyl group which may be protected with a protective group, or a halogen atom etc., can readily be produced (i) by permitting a microorganism belonging to the genus Torulaspora, the genus Candida, the genus Pichia or the like to act on a phenylacetone derivative and asymmetrically reducing the compound, or (ii) by sterically inverting an (R)-enantiomer. (R,R)-1-phenyl-2-[(2-phenyl-1-methylethyl)amino]ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (I). The ethanol derivative is useful as an anti-obesity agent and the like.

  以下是翻译结果： 以下公式（I）所示，其中R1和R2代表低碳基等，或R1和R2可能一起形成亚烷基等；R3、R4和R5代表氢原子等；X代表一个羟基，它可以用保护基保护，或者是卤原子等。可以通过以下方法轻松地制备出（S）-1-苯基-2-取代丙烷衍生物：（i）让属于酵母菌属Torulaspora、Candida、Pichia等的微生物作用于苯乙酮衍生物并不对称还原化合物，或者（ii）通过立体反演（R）-对映体。从公式（I）的化合物可以轻松地获得具有高光学纯度的（R，R）-1-苯基-2-［（2-苯基-1-甲基乙基）氨基］乙醇衍生物。该乙醇衍生物可用作抗肥胖剂等。