(R)-1-phenylethylammonium | 80158-36-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-1-phenylethylammonium
• 英文别名: (S)-1-phenylethylammonium；1-phenylethylammonium；(1S)-1-phenylethanaminium；[(1S)-1-phenylethyl]azanium
• CAS: 80158-36-7
• 化学式: C₈H₁₁N*H
• 分子量: 122.19
• InChiKey: RQEUFEKYXDPUSK-ZETCQYMHSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  27.6
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  [(3S,8S,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2S)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 2-[(2S,16S)-2,16-dimethyl-3,6,9,12,15-pentaoxa-18,19,20-triazabicyclo[15.2.1]icosa-1(19),17(20)-dien-18-yl]acetate 、 (R)-1-phenylethylammonium 生成 [(3S,8S,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2S)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 2-[(2S,16S)-2,16-dimethyl-3,6,9,12,15-pentaoxa-18,19,20-triazabicyclo[15.2.1]icosa-1(19),17(20)-dien-18-yl]acetate;[(1S)-1-phenylethyl]azanium
  参考文献：
  名称：

  LI, YI;ECHEGOYEN, LUIS;MARTINEZ-DIAZ, VICTORIA M.;MENDOZA, JAVIER DE;TORR+, J. ORG. CHEM., 56,(1991) N3, C. 4193-4196

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-(-)-N-乙酰基-1-甲基苄胺 、 水 生成 (R)-1-phenylethylammonium 、 乙酸盐
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Hydrogen Bonding Ring Patterns of Chiral Dibenzoyltartrate in a Series of Hydrated Ammonium Carboxylate Salts with Chiral 1-Phenylethylammonium
  作者：Andreas Lemmerer

  DOI：10.1007/s10870-012-0361-2

  日期：2012.11

  A number of ammonium carboxylate salts using the cations (R)-1-phenylethylammonium (R–C) and (S)-1-phenylethylammonium (S–C), and the anions (2R,3R)-(-)-2,3-di-p-toluoyloxybutanedioate (RR-A) and (2S,3S)-(+)-2,3-di-p-toluoyloxybutanedioate (SS-A) were prepared by using different ratios of the R and S cations to the two anions. In particular, the crystal structures of the ammonium carboxylate salts (R-A)2 ·(RR-A)·(H2O)·(MeOH) (1), (R–C)3 ·(S–C)·(RR-A)2 ·(H2O)5 (2), (R–C)·(S–C)·(RR-A)·(H2O)8 (3), (R–C)·(S–C)3 ·(RR-A)2 ·(H2O)6 ·(MeOH) (4), (S–C)2 ·(RR-A)·(H2O)2 (5), (R–C)2 ·(SS-A)·(H2O)2 (6) and (S–C)2 ·(SS-A)·(H2O)·(MeOH) (7) were synthesized and their solid state structures determined by low temperature single crystal X-ray diffraction. The molecular salts were prepared by solution crystallization of the carboxylic acids with the respective amines in a 1:2 stoichiometric ratio, and crystallized out as hydrated and solvated salts. The salts 1–5 all have the same anion species, but with the cation chiral ratio varying from R to S, and the salts 6 and 7 feature the SS-A anion. The crystal structure of 1 belongs to the orthorhombic space group P212121 with a = 7.9812(1), b = 10.3781(2), c = 41.1897(6) Å. The crystal structure of 2 belongs to the monoclinic space group P21 with a = 12.7316(2), b = 18.0107(3), c = 15.0977(2) Å and β = 101.755(1)°. The crystal structure of 3 belongs to the monoclinic space group P21 with a = 13.9615(2), b = 18.0549(2), c = 15.1335(2) Å and β = 111.397(1)°. The crystal structure of 4 belongs to the monoclinic space group P21 with a = 10.3381(5), b = 25.6109(12), c = 13.3450(4) Å and β = 91.504(3)°. The crystal structure of 5 belongs to the orthorhombic space group P212121 with a = 10.3104(2), b = 13.4412(2), c = 24.6998(6) Å. The crystal structure of 6 belongs to the orthorhombic space group P212121 with a = 10.3149(3), b = 13.4377(7), c = 24.7113(13) Å. The crystal structure of 7 belongs to the orthorhombic space group P212121 with a = 7.9755(6), b = 10.3946(7), c = 41.186(3) Å. The changes in cation and anion species produces 1-D ribbons in 1 and 7, and 2-D layers in 2–6, with corresponding changes in the hydrogen bonded ring patterns linking the ionic species together using charge-assisted N+–H···O−, O–H···O− and N+–H···O hydrogen bonds. Hydrogen bonding ring patterns of chiral dibenzoyltartrate in a series of hydrated ammonium carboxylate salts with chiral 1-phenylethylammonium. The three most commonly observed ring patterns in hydrated chiral ammonium carboxylate salts.

  一些羧酸铵盐使用阳离子(R)-1-苯基乙基铵(R-C)和(S)-1-苯基乙基铵(S-C)，阴离子(2R,3R)-(-)-2、通过使用 R 和 S 阳离子与两种阴离子的不同比例，制备了 (2R,3R)-(-)-2,3-二对甲苯甲酰基氧基丁二酸（RR-A）和 (2S,3S)-(+)-2,3-二对甲苯甲酰基氧基丁二酸（SS-A）。特别是羧酸铵盐 (R-A)2 -(RR-A)-(H2O)-(MeOH) (1)、(R-C)3 -(S-C)-(RR-A)2 -( )5 (2)、(R-C)-(S-C)-(RR-A)-( )8 (3)、(R-C)-(S-C)3 -(RR-A)2 -( )6 -(MeOH) (4) 的晶体结构、合成了 (S-C)2 -(RR-A)-( )2 (5)、(R-C)2 -(SS-A)-( )2 (6) 和 (S-C)2 -(SS-A)-( )-(MeOH) (7)，并通过低温单晶 X 射线衍射测定了它们的固态结构。分子盐是通过羧酸与相应胺按 1:2 的化学计量比进行溶液结晶制备的，并结晶成水合盐和溶解盐。盐 1-5 都具有相同的阴离子种类，但阳离子的手性比例从 R 到 S 不等，盐 6 和盐 7 则具有 SS-A 阴离子。1 的晶体结构属于正交空间群 P212121，a = 7.9812(1), b = 10.3781(2), c = 41.1897(6) Å.2 的晶体结构属于单斜空间群 P21，a = 12.7316(2)，b = 18.0107(3)，c = 15.0977(2) Å，β = 101.755(1)°。3 的晶体结构属于单斜空间群 P21，a = 13.9615(2), b = 18.0549(2), c = 15.1335(2) Å 和 β = 111.397(1)°。4 的晶体结构属于单斜空间群 P21，a = 10.3381(5)，b = 25.6109(12)，c = 13.3450(4) Å 和 β = 91.504(3)°。5 的晶体结构属于正交空间群 P212121，a = 10.3104(2), b = 13.4412(2), c = 24.6998(6) Å.6 的晶体结构属于正交空间群 P212121，a = 10.3149(3), b = 13.4377(7), c = 24.7113(13) Å.7 的晶体结构属于正交空间群 P212121，a = 7.9755(6)，b = 10.3946(7)，c = 41.186(3) 埃。阳离子和阴离子种类的变化在 1 和 7 中产生了一维带状，在 2-6 中产生了二维层，利用电荷辅助 N+-H--O-、O-H--O- 和 N+-H-O 氢键将离子种类连接在一起的氢键环模式也发生了相应的变化。手性二苯甲酰基酒石酸盐与手性 1-苯基乙基铵的一系列水合羧酸铵盐中的氢键环模式。水合手性羧酸铵盐中最常观察到的三种环模式。
• Process for the preparation of (+)-(1R)
  申请人：Firmenich SA

  公开号：US05728866A1

  公开（公告）日：1998-03-17

  A method for preparing 3-oxo-2-pentyl-1-cyclopentaneacetic acid or methyl 3-oxo-2-pentyl-1-cyclopentaneacetate, essentially in the form of the (+)-(1R)-cis isomer thereof. The method includes the steps of (a) catalytically hydrogenating a compound of the formula (I), ##STR1## wherein M is a hydrogen atom, an alkali metal or alkaline earth metal atom, or a group NR.sub.4, where R is a hydrogen or a lower alkyl radical, in a suitable solvent and in the presence of a catalyst consisting of an Ru(II) complex comprising chiral ligands that contain a 2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl (BINAP) radical or a 1,2-bis(2,5-dialkylphospholano)benzyl (DuPHOS) radical, wherein the alkyl is a C.sub.2 or C.sub.3 radical, to give a compound of formula (II), ##STR2## wherein M has the meaning given above, essentially in the form of the (+)-(1R)-cis isomer thereof; (b) if required, acidifying, in a per se known manner, the compound of formula (II), wherein M is an alkali metal or alkaline earth metal atom, or a group N.sub.4, where R is hydrogen or a lower alkyl radical, to give (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid; and (c) if required, esterifying the resulting (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid under suitable conditions to form methyl (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate.

  本发明涉及一种制备3-氧代-2-戊基-1-环戊基乙酸或甲基3-氧代-2-戊基-1-环戊基乙酸酯的方法，其基本上呈现出(+)-(1R)-顺式异构体的形式。该方法包括以下步骤：(a)在适当的溶剂中，在Ru（II）配合物催化剂的存在下，催化氢化式（I）的化合物， 其中M是氢原子，碱金属或碱土金属原子，或基团NR.sub.4，其中R是氢或较低的烷基基团，所述催化剂包括含有2,2'-双(二苯基膦基)-1,1'-二萘基(BINAP)基团或1,2-双(2,5-二烷基膦氧基)苯基(DuPHOS)基团的手性配体，其中烷基是C.sub.2或C.sub.3基团，以得到式（II）的化合物， 其中M具有上述给定的含义，基本上呈现出(+)-(1R)-顺式异构体的形式；(b)如有必要，以已知的方式酸化式（II）的化合物，其中M是碱金属或碱土金属原子，或基团N.sub.4，其中R是氢或较低的烷基基团，以得到(+)-(1R)-顺式-3-氧代-2-戊基-1-环戊基乙酸；以及(c)如有必要，以适当的条件酯化所得的(+)-(1R)-顺式-3-氧代-2-戊基-1-环戊基乙酸，以形成甲基(+)-(1R)-顺式-3-氧代-2-戊基-1-环戊基乙酸酯。
• Hwang B.Y.; Ko S.H.; Park H.Y., J Microbiol Biotechnol, 2008, 1017-7825, 48-54
  作者：Hwang B.Y.、Ko S.H.、Park H.Y.、Seo J.H.、Lee B.S.、Kim B.G.

  DOI：——

  日期：——