(R)-1-[3,5-二(三氟甲基)苯基)乙胺 | 127733-47-5

• 物质功能分类: 有机原料 - 氨基化合物
• 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: (R)-1-[3,5-二(三氟甲基)苯基)乙胺
• 中文别名: (R)-1-[3,5-双(三氟甲基)苯基]乙胺
• 英文名称: (R)-α-(3,5-bis(trifluoromethyl)phenyl)ethylamine
• 英文别名: (R)-α-methyl-3,5-bis(trifluoromethyl)benzylamine；(S)-alpha-methyl-3,5-bis(trifluoromethyl)-benzenemethanamine；(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethylamine；(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethanamine
• CAS: 127733-47-5
• 化学式: C₁₀H₉F₆N
• mdl: MFCD03093012
• 分子量: 257.179
• InChiKey: PFVWEAYXWZFSSK-RXMQYKEDSA-N

物化性质

• 沸点：
  168.9±35.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2921499090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  (RS)-1-[3,5-双(三氟甲基)苯基]乙胺	(RS)-α-methyl-3,5-bis(trifluoromethyl)benzenemethanamine	187085-97-8	C10H9F6N	257.179
  ——	N-(1-(3,5-bis(trifluoromethyl)phenyl)ethyl)formamide	742097-67-2	C11H9F6NO	285.189
  ——	(S)-N-[(S)-alpha-Methylbenzyl]-3,5-bis(trifluoromethyl)-alpha-methylbenzenemethanamine	384824-41-3	C18H17F6N	361.33
  ——	[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethyl]-((S)-1-phenyl-ethyl)-amine	511256-29-4	C18H17F6N	361.33
  3,5-双三氟甲基苯乙酮	3,5-bis(trifluoromethyl)phenyl methyl ketone	30071-93-3	C10H6F6O	256.147
  ——	3,5-bis(trifluoromethyl)acetophenone O-methyloxime	127733-38-4	C11H9F6NO	285.189

反应信息

• 作为反应物：
  描述：

  (R)-1-[3,5-二(三氟甲基)苯基)乙胺 、 Thiazole-4-carboxylic acid (4-isothiocyanato-phenyl)-amide 以 乙腈 为溶剂， 生成 Thiazole-4-carboxylic acid (4-{3-[(R)-1-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-thioureido}-phenyl)-amide
  参考文献：
  名称：

  Thiourea inhibitors of herpes viruses. Part 2: N-Benzyl-N′-arylthiourea inhibitors of CMV

  摘要：

  A series of highly potent thiourea inhibitors of cytomegalovirus (CMV) with improved stability properties was prepared and evaluated. Compound 29 inhibited the virus in cultured HFF cells with IC50 of 0.2 nM. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.04.093
• 作为产物：
  描述：

  (S,E)-N-(1-(3,5-bis(trifluoromethyl)phenyl)ethylidene)-1-phenylethanamine 在 palladium on activated charcoal sodium tetrahydroborate 、 水 、 氢气 作用下， 以 甲醇 为溶剂， 60.0 ℃ 、500.0 kPa 条件下， 反应 24.0h， 生成 (R)-1-[3,5-二(三氟甲基)苯基)乙胺
  参考文献：
  名称：

  受芳香环上三氟甲基取代基影响的双（α-甲基苄基）胺衍生物的高度区域选择性氢解。

  摘要：

  [反应：见正文]双（α-甲基苄基）胺衍生物的高度区域选择性氢解反应不受电子效应的影响，而是受到三氟甲基取代基在芳香环上的空间效应的影响，从而提供了实用的不对称合成三氟甲基取代的化合物α-苯基乙胺。

  DOI：

  10.1021/ol034014w

文献信息

• Indanyl-piperazine compounds
  申请人：De Nanteuil Guillaume

  公开号：US20060223830A1

  公开（公告）日：2006-10-05

  A compound selected from those of formula (I): wherein: R 3 represents a hydrogen atom, and R 1 and R 2 together with the carbon atoms carrying them form a benzene, naphthalene or quinoline ring structure, each of the ring structures being optionally substituted, or R 1 represents a hydrogen atom, and R 2 and R 3 together with the carbon atoms carrying them form a benzene, naphthalene or quinoline ring structure, each of the ring structures being optionally substituted, n represents 1 or 2, —X— represents a group selected from —(CH 2 ) m —O-Ak-, —(CH 2 ) m —NR 4 -Ak-, —(CO)—NR 4 -Ak- and —(CH 2 ) m —NR 4 -(CO)—, m represents an integer between 1 and 6 inclusive, Ak represents an optionally substituted alkylene chain, and R 4 represents a hydrogen atom or an alkyl group, Ar represents an aryl or heteroaryl group, its enantiomers, diasteroisomers, and addition salts thereof with a pharmaceutically acceptable acid. Medical products containing the same which are useful in the treatment of conditions requiring a serotonin reuptake inhibitor and/or NK 1 antagonist.

  从公式（I）中选择的化合物：其中：R3代表氢原子，R1和R2与携带它们的碳原子一起形成苯、萘或喹啉环结构，每个环结构可选择地被取代，或R1代表氢原子，R2和R3与携带它们的碳原子一起形成苯、萘或喹啉环结构，每个环结构可选择地被取代，n代表1或2，-X-代表从-(CH2)m-O-Ak-、-(CH2)m-NR4-Ak-、-(CO)-NR4-Ak-和-(CH2)m-NR4-(CO)-中选择的基团，m代表1到6之间的整数，Ak代表可选择地取代的烷基链，R4代表氢原子或烷基基团，Ar代表芳基或杂环芳基基团，它的对映异构体、顺反异构体和与药用酸形成的加合物。含有这些化合物的医药产品在治疗需要血清素再摄取抑制剂和/或NK1拮抗剂的病症中有用。
• Process for producing optically active 1-(fluoro- or trifluoromethyl-substituted phenyl) ethylamine and process for purifying same
  申请人：Central Glass Company, Limited

  公开号：US06797842B2

  公开（公告）日：2004-09-28

  An optically active 1-(fluoro- or trifluoromethyl-substituted phenyl)ethylamine is produced with high optical purity and in an industrially simple and efficient manner by asymmetrically reducing an optically active imine, obtained by dehydration and condensation of a fluoro- or trifluoromethyl-substituted phenylmethyl ketone and an optically active primary amine under acidic conditions, using a hydride reducing agent to convert to an optically active secondary amine, and subjecting the secondary amine or its salt of an inorganic acid or organic acid to hydrogenolysis. In addition, an optically active 1-(fluoro- or trifluoromethyl-substituted phenyl)ethylamine is purified to an even higher optical purity in an industrially simple and efficient manner by converting the optically active secondary amine of the synthetic intermediate obtained by asymmetric reduction, or an optically active 1-(3,5-bis-trifluoromethylphenyl)ethylamine, one of the target compounds, to an inorganic or organic acid salt followed by recrystallization purification. This ethylamine is an important intermediate of pharmaceuticals and agricultural chemicals.

  通过在酸性条件下将氟代或三氟甲基取代的苯甲基酮和光学活性的初级胺脱水和缩合得到的光学活性亚胺，再使用氢化还原剂将其转化为光学活性的二级胺，然后将这个二级胺或其无机酸或有机酸盐进行氢解，可以以高光学纯度和在工业上简单高效的方式生产光学活性的1-(氟代或三氟甲基取代的苯基)乙胺。此外，通过将通过不对称还原得到的合成中间体的光学活性二级胺，或目标化合物之一的光学活性1-(3,5-双三氟甲基苯基)乙胺转化为无机或有机酸盐，然后进行重结晶纯化，可以以工业上简单高效的方式将光学活性的1-(氟代或三氟甲基取代的苯基)乙胺提纯至更高的光学纯度。这种乙胺是制药和农药化学品的重要中间体。
• [EN] ARYLAMIDE DERIVATIVES AS TTX-S BLOCKERS<br/>[FR] DÉRIVÉS D'ARYLAMIDE EN TANT QU'AGENTS BLOQUANTS DE TTX-S
  申请人：RAQUALIA PHARMA INC

  公开号：WO2012053186A1

  公开（公告）日：2012-04-26

  The present invention relates to arylamide derivatives which have blocking activities of voltage gated sodium channels as the TTX-S channels, and which are useful in the treatment or prevention of disorders and diseases in which voltage gated sodium channels are involved. The invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which voltage gated sodium channels are involved.

  本发明涉及具有对电压门控钠通道（如TTX-S通道）具有阻塞活性的芳基酰胺衍生物，用于治疗或预防涉及电压门控钠通道的疾病和疾病。该发明还涉及包含这些化合物的药物组合物以及在预防或治疗涉及电压门控钠通道的这类疾病中使用这些化合物和组合物。
• ARYLAMIDE DERIVATIVES AS TTX-S BLOCKERS
  申请人：Yamagishi Tatsuya

  公开号：US20140336377A1

  公开（公告）日：2014-11-13

  The present invention relates to arylamide derivatives which have blocking activities of voltage gated sodium channels as the TTX-S channels, and which are useful in the treatment or prevention of disorders and diseases in which voltage gated sodium channels are involved. The invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which voltage gated sodium channels are involved.

  本发明涉及一种芳基酰胺衍生物，其具有阻断电压门控钠通道（如TTX-S通道）的活性，并且在涉及电压门控钠通道的疾病和疾病的治疗或预防中有用。本发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在涉及电压门控钠通道的这种疾病的预防或治疗中的使用。
• Efficient biosynthesis of (R)− 1-[3,5-bis(trifluoromethyl)phenyl]ethanamine with self-assembled dual-enzyme clusters
  作者：Yuan Lu、Jinmei Wang、Pengpeng Cheng、Chuyue Zhang、Jinghua Li、Zhimin Ou

  DOI：10.1016/j.procbio.2023.10.003

  日期：2023.11

  SpyCatcher-ATA117 (5 µM) and SpyTag-ADH (5 µM) were covalently combined to form self-assembled dual-enzyme clusters (DENCs) at 4 °C for 3 h. The successful assembly of DENCs was verified using sodium dodecyl sulfate polyacrylamide gel electrophoresis (SDS-PAGE), transmission electron microscopy (TEM), scanning electron microscopy (SEM), and dynamic light scattering (DLS). DENCs improved the storage

  纯化的 SpyCatcher-ATA117 (5 µM) 和 SpyTag-ADH (5 µM) 在 4 °C 下共价结合 3 小时，形成自组装双酶簇 (DENC)。使用十二烷基硫酸钠聚丙烯酰胺凝胶电泳（SDS-PAGE）、透射电子显微镜（TEM）、扫描电子显微镜（SEM）和动态光散射（DLS）验证了DENC的成功组装。与游离双酶相比，DENCs的储存稳定性提高了36.2%，pH稳定性提高了11.2%。使用 DENC 合成了56.89 g/L ( R )− 1-[3,5-双(三氟甲基)苯基]乙胺 ( R -BPA)，在 45 °C 下具有高产率 (99.9%) 和高对映体过量 (99.9%) pH 9 24 小时。此外，DENCs在R - BPA的制备中重复使用5个循环后，仍保留了78%以上的初始活性。由此，DENCs成功形成，并实现了高效胺化，为通过不对称转氨级联反应高效生物合成手性胺提供了一种新的生物催化剂。