(+)-<1'S,2'S>-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4-methylenedioxyphenyl)acetamide | 247118-52-1

• 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: (+)-<1'S,2'S>-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4-methylenedioxyphenyl)acetamide
• 英文别名: 2-(1,3-benzodioxol-5-yl)-N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylacetamide
• CAS: 247118-52-1
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: LOYASWYCAXHGPI-ORAYPTAESA-N

物化性质

• 沸点：
  524.4±50.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-<1'S,2'S>-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4-methylenedioxyphenyl)acetamide 在 正丁基锂 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2S)-2-amino-1-(3,4-dimethoxyphenyl)-2-(3,4-methylenedioxyphenyl)ethanone
  参考文献：
  名称：

  Asymmetric synthesis of 1,2-diaryl-2-amino ethanols

  摘要：

  A straightforward procedure for the asymmetric synthesis of 1,2-diaryl-2-amino ethanols is described. The key step relies on the diastereoselective electrophilic amination of the enolates derived from the corresponding (S,S)-(+)-pseudoephedrine arylacetamides with di-tert-butylazodicarboxylate, followed by a hydrolysis/hydrogenolysis procedure to yield alpha-amino amide derivatives with a very high degree of diastereoselection. These substrates were subsequently Subjected to a non-racemizing 1,2-addition step with several aryllithium reagents to yield the corresponding alpha-amino ketones which, upon diastereoselective reduction with NaBH4 afforded the desired beta-amino alcohols as single enantiomers with 1,2-anti relative configuration. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00181-7
• 作为产物：
  描述：

  胡椒乙酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 (+)-<1'S,2'S>-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4-methylenedioxyphenyl)acetamide
  参考文献：
  名称：

  首次立体控制合成12-甲基-六氢苯并[ c ]菲啶生物碱

  摘要：

  从通过（+）-（S，S）-伪麻黄碱基芳基乙酰胺烯醇酸酯的不对称烯丙基化制备的手性非外消旋2-芳基-2-芳基-4-戊烯酸开始，立体选择性地合成了12-甲基B / C六氢苯并[ c ]菲啶。随后的转化（Friedel-Crafts酰化，立体控制的还原胺化，Pictet-Spengler环化和PPA催化的阳离子环化）导致了对映体富集的六氢苯并[ c ]菲啶的合成，其中所有新的立体异构中心的顺序形成均由起始位点控制手性酸。

  DOI：

  10.1016/s0957-4166(99)00167-6

文献信息

• Asymmetric Synthesis of Arylglycines and Their Use as Chiral Templates for the Stereocontrolled Synthesis of 7,8-Disubstituted 3-Aryl-1,2,3,4-tetrahydroisoquinolin-4-ols
  作者：Eneritz Anakabe、Jose L. Vicario、Dolores Badía、Luisa Carrillo、Victoria Yoldi

  DOI：10.1002/1099-0690(200111)2001:22<4343::aid-ejoc4343>3.0.co;2-d

  日期：2001.11

  obtained turned out to be excellent chiral templates for the production of chiral, nonracemic 7,8-disubstituted 3-aryl-1,2,3,4-tetrahydroisoquinolines, through use of a synthetic sequence involving: (1) reduction of the arylglycines to the parent arylglycinols, (2) N-benzylation with appropriately substituted aromatic aldehydes and (3) Swern oxidation followed by acid-catalysed cyclization of the obtained

  一种用于不对称合成芳基甘氨酸的合成技术已得到优化，只需四步即可达到目标氨基酸，收率良好，对映体过量超过 99%。关键步骤包括基于 (S,S)-(+)-伪麻黄碱的芳基乙酰胺烯醇化物与二叔丁基偶氮二羧酸酯的立体控制的亲电胺化反应。由此获得的芳基甘氨酸被证明是用于生产手性非外消旋 7,8-二取代 3-芳基-1,2,3,4-四氢异喹啉的极好手性模板，通过使用合成序列，包括：（1）还原将芳基甘氨酸转化为母体芳基甘氨醇，(2) 用适当取代的芳香醛进行 N-苄基化和 (3) Swern 氧化，然后酸催化所得 α-氨基醛的环化。
• Asymmetric synthesis of arylglycine amino acids using (S,S)-(+)-pseudoephedrine derived amides
  作者：Jose L. Vicario、Dolores Badía、Esther Domínguez、Ana Crespo、Luisa Carrillo、Eneritz Anakabe

  DOI：10.1016/s0040-4039(99)01475-6

  日期：1999.9

  Arylglycine aminoacids were obtained in good yields and with enantiomeric excesses higher than 99% by using an asymmetric amination reaction protocol on (S,S)-(+)-pseudoephedrine based arylacetamide enolates with di-tert-butylazodicarboxylate. Subsequent hydrazinolysis and hydrolysis yielded the target aminoacids.

  通过在基于（S，S）-（+）-伪麻黄碱的芳基乙酰胺烯酸酯和二叔丁基偶氮二羧酸酯上使用不对称胺化反应方案，可以以高收率获得对映体过量，且对映体过量率高于99％。随后的肼解和水解产生目标氨基酸。
• The first stereocontrolled synthesis of isoflavanones
  作者：Jose L. Vicario、Dolores Badı́a、Esther Domı́nguez、Mónica Rodrı́guez、Luisa Carrillo

  DOI：10.1016/s0040-4039(00)01464-7

  日期：2000.10

  The first asymmetric synthesis of isoflavanones has been performed employing a stereocontrolled aldol reaction between an (S,S)-(+)-pseudoephedrine arylacetamide and para-formaldehyde as the key step. (C) 2000 Elsevier Science Ltd. All rights reserved.
• An easy and straightforward approach to the asymmetric synthesis of isoflavanones
  作者：Jose L. Vicario、Dolores Badı́a、Luisa Carrillo

  DOI：10.1016/s0957-4166(02)00831-5

  日期：2003.2

  Isoflavanones 4a-d have been prepared in a stereocontrolled fashion using (S.S)-(+)-pseudoephedrine as a chiral auxiliary. The employed synthetic pathway consists of only four steps and involves initial formation of the stereogenic centre via diastereoselective aldol reaction of pseudoephedrine arylacetamides la-c with formaldehyde, followed by aryl ether formation under Mitsunobu conditions, removal of the chiral auxiliary by hydrolysis and final Friedel-Crafts intramolecular acylation. (C) 2003 Elsevier Science Ltd. All rights reserved.
• The first stereocontrolled synthesis of 12-methyl-hexahydrobenzo[c]phenanthridine alkaloids
  作者：Jose L. Vicario、Dolores Badı́a、Esther Domı́nguez、Ana Crespo、Luisa Carrillo

  DOI：10.1016/s0957-4166(99)00167-6

  日期：1999.5

  synthesized stereoselectively starting from chiral nonracemic 2-aryl-4-pentenoic acids prepared by asymmetric allylation of (+)-(S,S)-pseudoephedrine-based arylacetamide enolates. Subsequent transformations (Friedel–Crafts acylation, stereocontrolled reductive amination, Pictet–Spengler cyclization and PPA catalyzed cationic cyclization) led to the synthesis of enantiomerically enriched hexahydroben

  从通过（+）-（S，S）-伪麻黄碱基芳基乙酰胺烯醇酸酯的不对称烯丙基化制备的手性非外消旋2-芳基-2-芳基-4-戊烯酸开始，立体选择性地合成了12-甲基B / C六氢苯并[ c ]菲啶。随后的转化（Friedel-Crafts酰化，立体控制的还原胺化，Pictet-Spengler环化和PPA催化的阳离子环化）导致了对映体富集的六氢苯并[ c ]菲啶的合成，其中所有新的立体异构中心的顺序形成均由起始位点控制手性酸。