(S)-(-)-2-氨基-3-甲基-1,1-二苯基丁烷 | 233772-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-(-)-2-氨基-3-甲基-1,1-二苯基丁烷
• 中文别名: (S)-(?)-2-氨基-3-甲基-1,1-二苯基丁烷
• 英文名称: (S)-3-methyl-1,1-diphenylbutan-2-amine
• 英文别名: (S)-(-)-2-Amino-3-methyl-1,1-diphenylbutane；(2S)-3-methyl-1,1-diphenylbutan-2-amine
• CAS: 233772-37-7
• 化学式: C₁₇H₂₁N
• 分子量: 239.36
• InChiKey: KJRIVAFIKUXDBL-KRWDZBQOSA-N

物化性质

• 熔点：
  73-76 °C (lit.)
• 稳定性/保质期：
  在指定条件下稳定，远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 安全说明：
  S26,S36
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-2-氨基-3-甲基-1,1-二苯基丁烷 在 五氯化磷 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 (3S,4R)-1-methyl-3-isopropyl-4-phenyl-3,4-dihydroisoquinoline
  参考文献：
  名称：

  Nicoletti; O'Hagan; Slawin, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 1, p. 116 - 121

  摘要：

  DOI：
• 作为产物：
  描述：

  (4S)-(-)-异丙基-5,5-二苯基-2-恶唑烷酮 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以72%的产率得到(S)-(-)-2-氨基-3-甲基-1,1-二苯基丁烷
  参考文献：
  名称：

  A short synthesis of (S)-α-(diphenylmethyl)alkyl amines from amino acids

  摘要：

  A range of (S)-alpha-(diphenylmethyl)alkyl amines were prepared from the corresponding (S)-alpha-amino acid ester hydrochlorides. These amines were derived by direct hydrogenation of their precursor oxazolidinones. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00095-6

文献信息

• [EN] AN IMPROVED ASYMMETRIC SYNTHESIS OF alpha-(DIARYLMETHYL) ALKYL AMINES<br/>[FR] SYNTHÈSE ASYMÉTRIQUE AMÉLIORÉE D'ALPHA-(DIARYLMÉTHYL)ALKYLAMINES
  申请人：PIRAMAL ENTPR LTD

  公开号：WO2019180627A1

  公开（公告）日：2019-09-26

  The present invention relates to an improved asymmetric synthesis of alpha- (diarylmethyl) alkyl amines (hereafter referred to as the compound (1)) or its pharmaceutically acceptable salt and derivatives. The process comprises an unusual substrate specific regioselective lithiation of alpha-diarylmethanes, followed by its highly diastereo selective addition to N-tert-butanesulfinylimines resulting in the selective formation of chiral alpha-(diarylmethyl) alkyl amines 4 and chiral amine 5; which on subsequently removing the sulfinyl group provides corresponding alpha-(diarylmethyl) alkyl amines (1) or relative chiral amines (1").

  本发明涉及一种改进的α-(二芳基甲基)烷基胺的不对称合成（以下简称为化合物（1））或其药用可接受的盐和衍生物。该过程包括对α-二芳基甲烷的不寻常底物特异性区域选择性锂化，然后将其高度对映选择性地加到N-叔丁基磺酰亚胺中，从而选择性地形成手性α-(二芳基甲基)烷基胺4和手性胺5；随后去除磺酰基可得到相应的α-(二芳基甲基)烷基胺（1）或相关手性胺（1"）。
• Asymmetric Synthesis of α-(Diarylmethyl) Alkyl Amines through Regioselective Lithiation of α-Diarylmethanes and the Diastereoselective Addition to Ellman’s Imines
  作者：Leleti Rajender Reddy、Sharadsrikar Kotturi、Yogesh Waman、Chirag Patel、Megha Danidharia、Rajesh Shenoy

  DOI：10.1021/acs.joc.8b00879

  日期：2018.6.15

  A highly regio- and diastereoselective lithiation/addition of α-diarylmethanes to N-tert-butanesulfinylimines is reported. This methodology also affords the preparation of enantiomerically pure α-(diarylmethyl) alkyl amines bearing quaternary centers.

  据报道，α-二芳基甲烷对N-叔丁烷亚磺酰亚胺具有高度的区域和非对映选择性锂化/加成。该方法还提供了带有季中心的对映体纯的α-（二芳基甲基）烷基胺的制备。
• The role of organic fluorine in directing alkylation reactions via lithium chelation
  作者：Kenny Tenza、Julian S. Northen、David O’Hagan、Alexandra M.Z. Slawin

  DOI：10.1016/j.jfluchem.2004.09.015

  日期：2004.11

  tertiary organic fluorine with hydrogen, no such effect is apparent, most probably due to adverse steric effects. The absolute and relative stereochemistry of the predominant diastereoisomers are confirmed by X-ray crystallography of suitable crystalline derivatives in each case. It is concluded that there is a potential role for organic-bound fluorine to become involved in lithium chelation in well-designed

  在酯与二异丙基氨基锂（LDA）和碘甲烷的α-甲基化过程中，氟甲基的氟对锂显示出可测量的螯合作用。将一系列酯与F，H和O进行比较，得到的非对映选择性与F螯合锂相对于H和O的中等能力相符。在涉及将叔有机氟与氢进行比较的第二种系统中，没有这样的对映体选择性。效果很明显，很可能是由于不利的空间效应。主要的非对映异构体的绝对和相对立体化学在每种情况下通过合适的结晶衍生物的X射线晶体学证实。结论是，在精心设计的烯醇盐烷基化体系中，有机结合的氟可能参与锂螯合。
• Process for preparing chiral compounds
  申请人：The University Court of the University of St. Andrews

  公开号：US07126028B1

  公开（公告）日：2006-10-24

  Process for the preparation of chiral compounds of formula (I) comprising contacting a compound of formula (II) with a source of hydrogen or halide; wherein A is a chiral center; X is selected from oxygen, sulphur and nitrogen; n is selected from 0 and 1 and is equal to the valence of X less 2; B is a fragment CR 3 2; Z is hydrogen or halogen; with the proviso that when X is nitrogen, n is 1, one of R 1 and two of R 2 are hydrogen, BZ is CHPh 2, the other R 1 and R 2 do not form together a five membered heterocyclic (pyrrolidone) ring; novel intermediates, novel compounds, polymers and libraries thereof and the use thereof as fine chemicals, and compositions thereof.

  制备式(I)手性化合物的过程包括将式(II)化合物与氢或卤素源接触；其中A是手性中心；X选择氧、硫或氮；n选择0和1，并等于X的价数减去2；B是片段CR 3 2；Z是氢或卤素；但当X为氮时，n为1，其中一个R 1 和两个R 2 是氢，BZ为CHPh 2，另一个R 1 和R 2 不形成五元杂环（吡咯烷酮）环；新的中间体、新的化合物、聚合物及其库以及作为精细化学品和其组成物的用途。
• Development of sterically hindered SPOs and enantioselective Ni−Al bimetallic catalyzed C−H cyclization of 4-oxoquinazolines with tethered alkenes
  作者：Yaqi Zhang、Qiang Ni、Bendu Pan、Long Jiang、Liqin Qiu

  DOI：10.1016/j.cclet.2022.108017

  日期：2022.11

  Ni−Al bimetallic catalysis of intramolecular enantioselective and regioselective C−H cyclization of 4-oxoquinazolines with tethered alkenes has been successfully developed. Some new secondary phosphine oxides (SPOs) with large steric hindrance (SPO6-11) were designed and successfully synthesized from readily available chiral amines or amino acids. The developed chiral SPOs as ligands or preligands demonstrate

  4-氧代喹唑啉与链烯烃的分子内对映选择性和区域选择性 C-H 环化的 Ni-Al 双金属催化已成功开发。设计了一些具有大空间位阻 (SPO6-11) 的新型二级氧化膦 (SPO)，并用现成的手性胺或氨基酸成功合成。所开发的手性 SPO 作为配体或预配体在不对称催化反应中表现出比报道的传统反应更高的效率。以高达 95% 的收率和 99% ee获得了一类新的手性三环吡咯并喹唑啉酮。