(2S)-2--3-phenyl-1-propanol | 91373-74-9

• 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: (2S)-2--3-phenyl-1-propanol
• 英文别名: N-(4-Methoxybenzyl)-L-phenylalaninol；(S)-2-(4′-methoxybenzyl)amino-3-phenylpropan-1-ol；(2S)-2-[(4-methoxyphenyl)methylamino]-3-phenylpropan-1-ol
• CAS: 91373-74-9
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: RLEWETXUFNVGPG-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2--3-phenyl-1-propanol 在 吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 ammonium cerium(IV) nitrate 、 四丁基氟化铵 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 106.67h， 生成 [(1S,2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenyl-1-(1,3-thiazol-2-yl)propyl] acetate
  参考文献：
  名称：

  Chelation- and Non-chelation-Controlled Addition of 2-(Trimethylsilyl)thiazole to .alpha.-Amino Aldehydes: Stereoselective Synthesis of the .beta.-Amino-.alpha.-hydroxy Aldehyde Intermediate for the Preparation of the Human Immunodeficiency Virus Proteinase Inhibitor Ro 31-8959

  摘要：

  DOI：

  10.1021/jo00129a057
• 作为产物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 11.5h， 生成 (2S)-2--3-phenyl-1-propanol
  参考文献：
  名称：

  分子内狄尔斯-阿尔德环加成向途径顺-融合Δ 5,6- -Hexahydroisoindol -1-酮细胞松弛素核心

  摘要：

  的合成的顺式-融合Δ 5,6- -hexahydroisoindol -1-酮细胞松弛素B的核心2 -B 5，K，Z 8，Z 9，Z 12 -Z 15，和Z 17已经建立从分子内狄尔斯开始–酰胺系的（8 E）-1,3,8-壬二烯的Al光反应。然后使反式融合的5 / 6-双环加合物经历高度立体选择性的C9-β-羟基化和C7-α-OH基的差向异构化。

  DOI：

  10.1021/acs.orglett.8b04129

文献信息

• Optically active N-substituted phenylalaninols and use thereof
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US04536601A1

  公开（公告）日：1985-08-20

  Optically active N-substituted phenylalaninols of the formula (I): ##STR1## wherein R is isopropyl, 1-ethylpropyl, cyclopentyl, cyclohexyl, cycloheptyl, 4-methylbenzyl, 4-methoxybenzyl, or 3,4-methylenedioxybenzyl; and acid addition salts thereof which are useful as a resolving agent, and a process for preparing D-3-acetylthio-2-methylpropionic acid which comprises reacting DL-3-acetylthio-2-methylpropionic acid with an optically active N-substituted phenylalaninol of the formula (I) to form diastereomeric salts, subjecting the formed diastereomeric salts to a fractional crystallization from a solvent to separate the D-acid salt from the L-acid salt, and then decomposing the D-acid salt with a mineral acid to give D-3-acetylthio-2-methylpropionic acid.

  光学活性的N-取代苯丙氨醇的化学式（I）：##STR1## 其中R是异丙基，1-乙基丙基，环戊基，环己基，环庚基，4-甲基苯甲基，4-甲氧基苯甲基或3,4-亚甲二氧基苯甲基；以及其酸加成盐，可用作分离剂。制备D-3-乙酰基硫基-2-甲基丙酸的过程包括将DL-3-乙酰基硫基-2-甲基丙酸与光学活性的N-取代苯丙氨醇的化学式（I）反应，形成对映异构体盐，将形成的对映异构体盐从溶剂中分馏结晶，分离出D-酸盐和L-酸盐，然后用矿酸分解D-酸盐，得到D-3-乙酰基硫基-2-甲基丙酸。
• Dynamic kinetic resolution during iron carbonyl promoted [6+2] ene-type reactions
  作者：Anthony J. Pearson、Xiaolong Wang

  DOI：10.1016/j.tetlet.2005.02.166

  日期：2005.4

  Intramolecular coupling of cyclohexadiene–Fe(CO)3 complexes with pendant alkenes, to form spirolactams, proceed with excellent stereocontrol, using chiral amide substrates that lead to dynamic kinetic resolution.

  环己二烯-Fe（CO）3配合物与侧链烯烃的分子内偶联，形成螺内酰胺，使用手性酰胺底物可实现动态动力学拆分，可进行出色的立体控制。
• Optically active N-substituted phenylalaninols and use therefor
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP0105696A1

  公开（公告）日：1984-04-18

  Optically active N-substituted phenylalaninols of the formula (I): wherein R is isopropyl, 1-ethylpropyl, cyclopentyl, cyclohexyl, cycloheptyl, 4-methylbenzyl, 4-methoxybenzyl, or 3,4-methylenedioxybenryl; and acid addition salts thereof which are useful as a resolving agent, and a process for preparing D-3-acetylthio-2-methylpropionic acid which comprises reacting DL-3-acetylthio-2-methylpropionic acid with an optically active N-substituted phenylalaninol of the formula (I) to form diastereomeric salts, subjecting the formed diastereomeric salts to a fractional crystallization from a solvent to separate the D-acid salt from the L-acid salt, and then decomposing the D-acid salt with a mineral acid to give D-3-acetylthio-2-methylpropionic acid.

  式(I)的光学活性 N-取代的苯丙氨醇： 其中 R 为异丙基、1-乙基丙基、环戊基、环己基、环庚基、4-甲基苄基、4-甲氧基苄基或 3,4-亚甲二氧基苄基；及其可用作溶解剂的酸加成盐，以及制备 D-3-乙酰巯基-2-甲基丙酸的工艺，该工艺包括使 DL-3-乙酰巯基-2-甲基丙酸与光学活性 N-取代的式 (I) 苯丙氨醇反应，形成非对映异构盐、将形成的非对映异构盐从溶剂中进行分馏结晶，以分离 D 酸盐和 L 酸盐，然后用矿物酸分解 D 酸盐，得到 D-3-乙酰硫基-2-甲基丙酸。
• Synthesis and Reactivity of Bicycles Derived from Tartaric Acid and α-Amino Acids:  A Novel Class of Conformationally Constrained Dipeptide Isosteres Based upon Enantiopure 3-Aza-6,8-dioxabicyclo[3.2.1]octane-7-carboxylic Acid
  作者：Antonio Guarna、Antonio Guidi、Fabrizio Machetti、Gloria Menchi、Ernesto G. Occhiato、Dina Scarpi、Sauro Sisi、Andrea Trabocchi

  DOI：10.1021/jo9904967

  日期：1999.10.1

  3-Aza-6,8-dioxabicyclo[3.2.1]octane-7-carboxylic acids (named BTAa) derived from (R,R), (S,S)-, or meso-tartaric acid and natural (L), unnatural (D), or unusual alpha-amino acids are described as conformationally constrained dipeptide isosteres. The general strategy developed for their preparation has required the transformation of the amino acids into the corresponding N-benzylamino alcohols, followed by the PyBroP-promoted condensation with the monomethyl ester of the suitable 2,3-di-O-isopropylidenetartaric acid. Oxidation of the hydroxy group to aldheyde and subsequent acid-catalyzed trans-acetalization with the two hydroxy groups of the tartaric acid moiety provided 3-aza-2-oxo-6,8-dioxabicyclo [3.2.1] octane-7-carboxylic acid methyl esters [named BTAa(O)] in good yield and, in most cases, as single enantiopure diastereoisomers. This strategy has been applied to the preparation of BTAa(O) starting from (R,R)-, (S,S)-, or meso-tartaric acid and glycine, L- and D-phenylalanine, L- and D-alanine, and (+/-)-phenylglycine. In the cases of glycine, L- and D-phenylalanine, and L- and D-alanine, the selective reduction by BH3. DMS of the amide group succeeding to the cyclization step, or the reduction of both amide and ester functions followed by reoxidation of the hydroxy to carboxylic group, provided in good yield the 3-aza-3-benzyl-6,8-dioxabicyclo[3.2.1]-octane-7-carboxylic acids (or their methyl ester) BTAa, having the side chain of the amino acid precursors at position 4. The stability and rigidity of the bicyclic skeleton, the complete control of all the stereocenters, the possibility of introducing the side chains of L- or D-amino acids, and the demonstrated compatibility with the conditions required for solid-phase peptide synthesis make the BTAa compounds potential dipeptide isosteres useful for the synthesis of modified peptides.
• Cyclic sulfamate from N-substituted 2-amino-3-phenyl-1-propanol and its nucleophilic reactions
  作者：Gregory J. White、Michael E. Garst

  DOI：10.1021/jo00009a045

  日期：1991.4