(S)-2,2,2-三氟-1-苯乙胺盐酸盐

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (S)-2,2,2-三氟-1-苯乙胺盐酸盐
• 中文别名: (S)-2,2,2-三氟-1-苯基乙胺盐酸盐
• 英文名称: (S)-2,2,2-trifluoro-1-phenylethan-1-amine hydrochloride
• 英文别名: [(1S)-2,2,2-trifluoro-1-phenylethyl]azanium;chloride
• 化学式: C₈H₈F₃N*ClH
• 分子量: 211.614
• InChiKey: LCQGOISHUDYBOS-FJXQXJEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  13
• 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：
  26
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4'-溴-2,2,2-三氟苯乙酮 在 甲醇 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 生成 (S)-2,2,2-三氟-1-苯乙胺盐酸盐
  参考文献：
  名称：

  Unprecedented Catalytic Asymmetric Reduction of N−H Imines

  摘要：

  Addition of lithium bis(trimethylsilyl)amide to perfluorinated ketones 1a-j affords (E)-N-TMS-ketimines 2a-j that are reduced in situ to afford racemic perfluoromethylated amine hydrochloride salts 3a-j in 54-97% yields. Solvolysis of the N-Si bond in MeOH leads to formation of bench-stable, isolable N-H imine Z/E isomer mixtures along with a methanol adduct. Enantioselective reduction of these three-component mixtures provides the first catalytic asymmetric synthesis of trifluoromethylated amines in 72-95% yields and 75-98% ee.

  DOI：

  10.1021/ol047431x

文献信息

• Catalytic Enantioselective Trifluoromethylation of Azomethine Imines with Trimethyl(trifluoromethyl)silane
  作者：Hiroyuki Kawai、Akihiro Kusuda、Shuichi Nakamura、Motoo Shiro、Norio Shibata

  DOI：10.1002/anie.200902457

  日期：——

  It′s a cinch! The title reaction with azomethine imines 1 uses an operationally simple procedure, based on the combination of the bromide salt of cinchona alkaloids (3) and KOH. The procedure is reliable and general. Trifluoromethyl‐substituted amines can be accessed by a two‐step deprotection of the product (S)‐2.

  c！基于金鸡纳生物碱（3）的溴化物盐和KOH的组合，使用偶氮甲亚胺1的标题反应使用操作简单的程序。该程序是可靠且通用的。可通过产品（S）-2的两步脱保护来获得三氟甲基取代的胺。
• Stereodivergent trifluoromethylation of <i>N</i>-sulfinylimines by fluoroform with either organic-superbase or organometallic-base
  作者：Nagender Punna、Takuya Saito、Mikhail Kosobokov、Etsuko Tokunaga、Yuji Sumii、Norio Shibata

  DOI：10.1039/c8cc01526k

  日期：——

  Here we have successfully demonstrated the first stereodivergent direct nucleophilic trifluoromethylation of N-sulfinylimines using the potent greenhouse gas “HFC-23, fluoroform” with an organic-superbase or an organometallic-base in high yields and selectivity.

  在这里，我们成功地证明了使用强效温室气体“ HFC-23，氟仿”与有机超碱或有机金属碱的高收率和选择性，N-亚磺酰亚胺的第一个立体发散性直接亲核三氟甲基化反应。
• Diastereoselective Addition of Organomagnesium and Organolithium Reagents to Chiral Trifluoromethyl<i>N</i>-<i>tert</i>-Butanesulfinyl Hemiaminals
  作者：Fabienne Grellepois、Abdelkhalek Ben Jamaa、Abdoulaye Gassama

  DOI：10.1002/ejoc.201300890

  日期：2013.10

  The asymmetric synthesis of trifluoromethylated tertiary and secondary carbinamines (α,α-dibranched and α-branched amines) was achieved by reaction of alkyl, aryl and allyl organomagnesium or organolithium reagents to trifluoromethyl N-tert-butanesulfinyl hemiaminals, bench-stable analogs of the corresponding ketoimines.

  通过烷基、芳基和烯丙基有机镁或有机锂试剂与三氟甲基 N-叔丁烷亚磺酰基半胺、三氟甲基 N-叔丁烷亚磺酰基半胺、三氟甲基 N-叔丁烷亚磺酰基半胺反应，实现三氟甲基化叔胺和仲胺（α,α-二支化和 α-支化胺）的不对称合成。相应的酮亚胺。
• Asymmetric Syntheses of 1-Aryl-2,2,2-trifluoroethylamines via Diastereoselective 1,2-Addition of Arylmetals to 2-Methyl-<i>N</i>-(2,2,2-trifluoroethylidene)propane-2-sulfinamide
  作者：Vouy Linh Truong、Madelaine S. Ménard、Isabelle Dion

  DOI：10.1021/ol063001q

  日期：2007.2.1

  N-tert-butanesulfinamide (S)-1 with trifluoroacetaldehyde hydrate 2a afforded 2-methyl-N-(2,2,2-trifluoroethylidene)propane-2-sulfinamide 3. Without isolation and purification, imine 3 was added to various aryllithium reagents to give highly diastereomerically enriched adducts 5a-g. Acidic methanolysis of 5a-g provided the desired 1-aryl-2,2,2-trifluoroethylamine hydrochloride compounds 6a-g. [reaction: see text]

  N-叔丁烷亚磺酰胺（S）-1与三氟乙醛水合物2a的缩合得到2-甲基-N-（2,2,2-三氟乙叉基）丙烷-2-亚磺酰胺3。无需分离和纯化，将亚胺3添加到各种芳基锂试剂生成高度非对映异构体富集的加合物5a-g。5a-g的酸性甲醇分解提供了所需的1-芳基-2,2,2-三氟乙胺盐酸盐化合物6a-g。[反应：请参见文字]。
• One-pot asymmetric synthesis of α-trifluoromethylated amines from α-trifluoromethyl ketones
  作者：Jian Xu、Zhen-Jiang Liu、Xian-Jin Yang、Li-Min Wang、Guan-Long Chen、Jin-Tao Liu

  DOI：10.1016/j.tet.2010.09.047

  日期：2010.11

  of (Rs)-N-tert-butanesulfinyl α-trifluoromethyl ketimines formed in situ from the corresponding α-trifluoromethyl ketones and N-tert-butanesulfinamide has been achieved, and either diastereomer of N-tert-butanesulfinyl α-trifluoromethyl amines was obtained in good yields with excellent diastereoselectivities (up to 99:1 dr) using NaBH4 and L-Selectride as the reductants, respectively.

  （非对映选择性还原卢比- ）ñ -叔-butanesulfinylα三氟甲基酮亚胺形成原位由相应的α-三氟甲基酮和ñ -叔-butanesulfinamide已经实现，并且或者非对映体ñ -叔-butanesulfinylα三氟甲基胺WAS分别使用NaBH 4和L-Selectride作为还原剂，可以得到具有良好非对映选择性（高达99：1 dr）的非对映选择性的高收率化合物。