(S)-(-)-N-(4-methoxyphenyl)-(1-phenylpentyl)amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-(-)-N-(4-methoxyphenyl)-(1-phenylpentyl)amine
• 英文别名: N-(4-methoxyphenyl)-α-butylbenzenemethaneamine；N-(4-methoxyphenyl)-1-phenylpentyl amine；4-methoxy-N-(1-phenylpentyl)aniline；(S)-N-(4-methoxyphenyl)-α-butylbenzenemethaneamine；4-methoxy-N-[(1S)-1-phenylpentyl]aniline
• 化学式: C₁₈H₂₃NO
• 分子量: 269.387
• InChiKey: RJHYEWKJJKBFBJ-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(1-phenylpentylidene)-4-anisidine 在 rac-(ethylene-1,2-bis(4,5,6,7-tetrahydro-1-indenyl))TiF₂ polymethylhydrosiloxane 、 苯硅烷 、 异丁胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 13.0h， 生成 (S)-(-)-N-(4-methoxyphenyl)-(1-phenylpentyl)amine 、 N-(4-methoxyphenyl)-α-butylbenzenemethaneamine
  参考文献：
  名称：

  A Method for the Asymmetric Hydrosilylation of N-Aryl Imines

  摘要：

  [GRAPHICS]The asymmetric reduction of N-aryl imines to yield chiral amines with enantiomeric excesses above 90% was achieved. Ethylenebis(eta(5)-tetrahydroindenyl)titanium difluoride ((EBTHI)TiF2, 1) was employed as the precatalyst with polymethylhydrosiloxane (PMHS) as the stoichiometric reducing agent. A variety of N-aryl imines derived from nonaromatic ketones were reduced with high ee.

  DOI：

  10.1021/ol005583w

文献信息

• Highly Enantioselective Reductive Amination of Simple Aryl Ketones Catalyzed by Ir−f-Binaphane in the Presence of Titanium(IV) Isopropoxide and Iodine
  作者：Yongxiang Chi、Yong-Gui Zhou、Xumu Zhang

  DOI：10.1021/jo026856z

  日期：2003.5.1

  Using an Ir-f-Binaphane complex as the catalyst, complete conversions and high enantioselectivies (up to 96% ee) were achieved in the asymmetric reductive amination of aryl ketones in the presence of Ti(O(i)()Pr)(4) and I(2). A simple and efficient method of synthesizing chiral primary amines has been realized.

  使用Ir-f-Binaphane配合物作为催化剂，在Ti（O（i）（）Pr）（4）存在下芳基酮的不对称还原胺化反应中，可实现完全转化和高对映选择性（高达96％ee） ）和I（2）。已经实现了一种简单有效的合成手性伯胺的方法。
• Chiral cyclometalated iridium complexes for asymmetric reduction reactions
  作者：Jennifer Smith、Aysecik Kacmaz、Chao Wang、Barbara Villa-Marcos、Jianliang Xiao

  DOI：10.1039/d0ob02049d

  日期：——

  A series of chiral cyclometalated iridium complexes have been synthesised by cyclometalating chiral 2-aryl-oxazoline and imidazoline ligands with [Cp*IrCl2]2. These iridacycles were studied for asymmetric transfer hydrogenation reactions with formic acid as the hydrogen source and were found to display various activities and enantioselectivities, with the most effective ones affording up to 63% ee

  通过将手性2-芳基-恶唑啉和咪唑啉配体与[Cp * IrCl 2 ] 2进行环化，合成了一系列手性环金属化铱配合物。对这些iridacycles进行了以甲酸为氢源的不对称转移氢化反应的研究，发现它们具有各种活性和对映选择性，最有效的酮类化合物在酮的不对称还原胺化反应中可提供高达63％ee的活性，而在酮中则可提供77％ee的活性。还原吡啶鎓离子。
• Studies on the Bisoxazoline- and (−)-Sparteine-Mediated Enantioselective Addition of Organolithium Reagents to Imines
  作者：Scott E. Denmark、Noriyuki Nakajima、Cory M. Stiff、Olivier J.-C. Nicaise、Michael Kranz

  DOI：10.1002/adsc.200800017

  日期：2008.5.5

  The enantioselective addition of organolithium reagents to N-anisyl aldimines promoted by chiral bisoxazolines and (-)-sparteine as external ligands is described. This reaction proceeds readily with a wide range of aldimine substrates (aliphatic, aromatic, olefinic) and organolithium nucleophiles (Me, n-Bu, Ph, vinyl) in excellent yields (81-99%) and with high enantioselectivities (up to 95.5:4.5 er)

  描述了在手性双恶唑啉和(-)-金雀花碱作为外部配体的促进下，有机锂试剂对映选择性加成到N-茴香基醛亚胺上。该反应可以使用多种醛亚胺底物（脂肪族、芳香族、烯烃）和有机锂亲核试剂（Me、n-Bu、Ph、乙烯基）轻松进行，收率优异（81-99%），并且具有高对映选择性（高达 95.5： 4.5 尔）。外部配体可以亚化学计量的量使用，尽管对映选择性略有减弱。对双恶唑啉结构特征的系统评估揭示了 C(4) 取代基的主要贡献和桥接取代基的次要影响。计算分析 (PM3) 为对映选择性的起源提供了清晰的合理解释。
• Asymmetric 1,2-addition of organolithiums to aldimines catalyzed by chiral ligand
  作者：Isao Inoue、Mitsuru Shindo、Kenji Koga、Kiyoshi Tomioka

  DOI：10.1016/s0040-4020(01)89376-5

  日期：1994.4

  An asymmetric 1,2-addition reaction of organolithiums with imines 3, 7 was catalysed by a 0.05–1.3 equivalent of a chiral amino ether 2 to provide the corresponding optically active amines 4, 8.

  与亚胺有机锂的不对称1,2-加成反应3,7用0.05-1.3当量的手性氨基醚催化的2，以提供相应的光学活性胺4,8。
• Synthesis and application of a new pseudo C2-symmetric tertiary diamine for the enantioselective addition of MeLi to aromatic imines
  作者：Quentin Perron、Alexandre Alexakis

  DOI：10.1016/j.tetasy.2007.10.018

  日期：2007.10

  A new tertiary pseudo C2-symmetric diamine derived from (1S,2S)-(+)-pseudoephedrine was synthesized and tested in the enantioselective addition of methyllithium on different aromatic imines. A comparative study with a similar C2-symmetric ligand derived from the cyclohexane diamine showed better reactivity and enantioselectivity up to 91%.

  合成了一种新的由（1 S，2 S）-（+）-伪麻黄碱衍生的叔伪C 2对称二胺，并在不同芳族亚胺上对甲基锂的对映选择性加成进行了测试。使用类似的衍生自环己烷二胺的C 2对称配体的比较研究显示了更高的反应性和对映选择性，最高可达91％。