(S)-(+)-2-N,N-dimethylamino-3-phenyl-1-propylchloride hydrochloride | 74492-03-8

• 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: (S)-(+)-2-N,N-dimethylamino-3-phenyl-1-propylchloride hydrochloride
• 英文别名: (+)-(S)-1-chloro-2-dimethylamino-3-phenylpropane hydrochloride；(S)-2-(dimethylamino)-3-phenylpropyl chloride hydrochloride；S-dimethyl(1-benzyl-2-chloroethyl)amine hydrochloride；S-1-Chloro-2-(dimethylamino)-3-phenylpropane, hydrochloride
• CAS: 74492-03-8
• 化学式: C₁₁H₁₆ClN*ClH
• 分子量: 234.169
• InChiKey: KWUHCYZKWOBDIU-MERQFXBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-N,N-dimethylamino-3-phenyl-1-propylchloride hydrochloride 在 正丁基锂 、 potassium tert-butylate 作用下， 反应 20.0h， 生成 [(S)-1-Benzyl-2-(benzyl-phenyl-phosphanyl)-ethyl]-dimethyl-amine
  参考文献：
  名称：

  聚合物负载的光学活性β-二甲基氨基烷基膦-镍催化剂的不对称格氏交叉偶联

  摘要：

  使用氯甲基化的聚苯乙烯制备了含有β-二甲基氨基烷基膦的新型聚合物配体，并将这些配体用于镍催化的仲烷基格氏试剂与乙烯基溴的不对称交叉偶联，得到约50％ee的偶联产物。

  DOI：

  10.1016/0040-4039(80)80090-6
• 作为产物：
  描述：

  (2S)-2-(dimethylamino)-3-phenylpropanoic acid 在 盐酸 、 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 (S)-(+)-2-N,N-dimethylamino-3-phenyl-1-propylchloride hydrochloride
  参考文献：
  名称：

  手性β-二甲基氨基烷基膦。镍配合物的高效配体催化不对称格利雅交叉偶联反应

  摘要：

  从氨基酸，（S）-丙氨酸，（S）-苯丙氨酸，（R）-苯甘氨酸，（S）-缬氨酸和（R）-叔亮氨酸开始制备手性β-二甲基氨基烷基膦。发现手性膦是镍催化的不对称格利雅（Grignard）交叉偶联反应的高效配体（光学收率38〜94％）。

  DOI：

  10.1016/s0040-4039(00)93629-3

文献信息

• Benzazepine and benzothiazepine derivatives
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04902684A1

  公开（公告）日：1990-02-20

  Vasodilating activity is exhibited by compounds having the formula ##STR1## wherein X can be --S--or --CH.sub.2 --; and R.sub.2 is ##STR2## depending upon the definition of X.

  具有通式##STR1##的化合物表现出血管舒张活性，其中X可以是--S--或--CH₂--；而R₂是##STR2##，这取决于X的定义。
• (η6-Arene)ruthenium(II) complexes containing enantiomerically pure (β-aminoalkyl)phosphines or a (β-aminoalkyl) phosphinite: synthesis, stereochemical and kinetic studies
  作者：Carmela G. Arena、Stefania Calamia、Felice Faraone、Claudia Graiff、Antonio Tiripicchio

  DOI：10.1039/b003514i

  日期：——

  The chiral P–N* ligands [(S)-2-(dimethylamino)-3-phenylpropyl]diphenylphosphine, (S)-phephos, 1, [(S)-2-(dimethylamino)-2-phenylethyl]diphenylphosphine, (S)-phglyphos, 2, [(S)-2-(dimethylamino)-3-methylbutyl]diphenylphosphine, (S)-valphos, 3, and [(+)-(2S,3R)-4-(dimethylamino)-3-methyl]-2-diphenylphosphinoxy-1,2-diphenylbutane, (+)-(2S,3R)-chiraldphos, 4, reacted with [Ru(η6-arene)Cl2]2 (arene = p-cymene, benzene or hexamethylbenzene), in dichloromethane or tetrahydrofuran solution, affording the corresponding [Ru(η6-arene)(P–N*)Cl2] complexes, 5, in which the P–N* acts as a monodentate P-bonded ligand. In methanol the same reactions easily afforded the corresponding chelate complexes [Ru(η6-arene)(P–N*)Cl]Cl. Using ligands 1–3, when the arene is p-cymene, 90∶10 diastereomeric mixtures of the cationic complexes have been obtained while only one diastereomer was formed in the corresponding reactions when the arene is benzene or hexamethylbenzene. The determination of the absolute configuration of the major products as RRu,SC diastereoisomers was made from the crystal structure and CD spectra comparison of the complex (RRu,SC)-[Ru(η6-p-MeC6H4Pri)(S-phglyphos)Cl]BF4. Complexes [Ru(η6-arene)(P–N*)Cl]Cl were also obtained by adding small amounts of methanol to solutions of [Ru(η6-arene)(P–N*)Cl2] in chloroform. A kinetic study, in CDCl3 solution containing variable amounts of methanol, on the chelation process in the neutral species [Ru(η6-arene)(P–N*)Cl2] showed first-order behaviour of the kobs values with the nucleophile (methanol) concentration. The pseudo-first-order rate constants are ascribed to replacement of Cl− by a molecule of methanol. A reaction mechanism is proposed.

  手性 PâN* 配体[(S)-2-(二甲基氨基)-3-苯基丙基]二苯基膦，(S)-phephos，1，[(S)-2-(二甲基氨基)-2-苯基乙基]二苯基膦、(S)-phglyphos, 2, [(S)-2-(二甲基氨基)-3-甲基丁基]二苯基膦, (S)-valphos, 3, 和 [(+)-(2S,3R)-4-(二甲基氨基)-3-甲基]-2-二苯基膦氧基-1、在二氯甲烷或四氢呋喃溶液中，[(+)-(2S,3R)-chiraldphos, 4]与[Ru(δ-6-蒈烯)Cl2]2（蒈烯=对-甲苯、苯或六甲基苯）反应、得到相应的[Ru(δ-6-烯烃)(PâN*)Cl2]配合物 5，其中 PâN* 作为单价 P 键配体。在甲醇中，同样的反应很容易得到相应的螯合物 [Ru(δ-6-蒈烯)(PâN*)Cl]Cl。在使用配体 1â3 时，当烯烃为对-甲苯时，可以得到 90â¶10 个非对映异构体的阳离子络合物混合物，而当烯烃为苯或六甲基苯时，在相应的反应中只能形成一个非对映异构体。根据(RRu,SC)-[Ru(δ-6-p-MeC6H4Pri)(S-phglyphos)Cl]BF4 复合物的晶体结构和 CD 光谱比较，确定了主要产物为 RRu,SC 非对映异构体的绝对构型。在氯仿中的[Ru(δ-6-蒈烯)(PâN*)Cl2]溶液中加入少量甲醇，也可得到络合物[Ru(δ-6-蒈烯)(PâN*)Cl]Cl。在含有不同量甲醇的 CDCl3 溶液中，对中性物质 [Ru(δ-6-烯)(PâN*)Cl2]的螯合过程进行的动力学研究表明，kobs 值随亲核剂（甲醇）浓度的变化呈一阶行为。伪一阶速率常数归因于 Clâ 被一分子甲醇置换。提出了一种反应机理。
• Stereoselective reactions. XIX. Asymmetric dihydroxylation of olefins by employing osmium tetroxide-chiral amine complexes.
  作者：Kiyoshi TOMIOKA、Yuichi SHINMI、Kunihiko SHIINA、Makoto NAKAJIMA、Kenji KOGA

  DOI：10.1248/cpb.38.2133

  日期：——

  Enantioselective dihydroxylation of E-stilbene afforded (1S, 2S)-1, 2-diphenyl-1, 2-ethanediol in 70% ee by employing a stoichiometric amount of osmium tetroxide-chiral amine 5, prepared from N-methylephedrine and 2-bromopyridine.

  使用一定量的四氧化锇手性胺 5（由 N-甲基麻黄碱和 2-溴吡啶制备）对 E-二苯乙烯进行对映体选择性二羟基化，可得到(1S, 2S)-1, 2-二苯基-1, 2-乙二醇，eee 为 70%。
• Unsymmetrical terdentate phosphorus-nitrogen-nitrogen (PNN) ligands: effect of the M/L ratio and the pendant group on stereoselectivity
  作者：Xiaohui Cheng、King Kuok (Mimi) Hii

  DOI：10.1016/s0957-4166(03)00361-6

  日期：2003.7

  Twelve novel, unsymmetrical terdentate pyrrolidine-based phosphorus-nitrogen ligands were prepared. These ligands promoted very high catalytic activity in the palladium-catalysed allylic substitution reactions of 1,3-diphenylpropenyl acetate with malonate esters (100% conversion at 0degreesC in <2 h). Enantioselectivities up to 94% were attained. An unusual effect of metal-to-ligand ratio was observed. Various structural features affecting the enantioselectivity and stereoinduction were examined and discussed. (C) 2003 Elsevier Ltd. All rights reserved.
• Chiral (.beta.-aminoalkyl)phosphines. Highly efficient phosphine ligands for catalytic asymmetric Grignard cross-coupling
  作者：Tamio Hayashi、Mitsuo Konishi、Motoo Fukushima、Koichi Kanehira、Takeshi Hioki、Makoto Kumada

  DOI：10.1021/jo00161a013

  日期：1983.7