1-(N-Benzyl-N-methylamino)cyclohexene | 61581-04-2

• 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: 1-(N-Benzyl-N-methylamino)cyclohexene
• 英文别名: 1-(benzylmethylamino)cyclohexene；N-Benzyl-N-methyl-1-cyclohexen-1-ylamin；N-(1-Cyclohexen-1-yl)-methylbenzylamin；Benzenemethanamine, N-1-cyclohexen-1-yl-N-methyl-；N-benzyl-N-methylcyclohexen-1-amine
• CAS: 61581-04-2
• 化学式: C₁₄H₁₉N
• 分子量: 201.312
• InChiKey: NTFTZRKYKDFJED-UHFFFAOYSA-N

物化性质

• 沸点：
  156-157 °C(Press: 15 Torr)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(N-Benzyl-N-methylamino)cyclohexene 生成 (+/-)-(1S,2S)-2-(N-benzyl-N-methylamino)cyclohexanol
  参考文献：
  名称：

  Boranes in Synthesis. 5. The Hydroboration of Enamines with Mono- and Dialkylboranes. Asymmetric Synthesis of .beta.-Amino Alcohols of Moderate Enantiomeric Purity from Aldehyde Enamines

  摘要：

  The hydroboration of both acyclic and cyclic aldehyde and ketone enamines with such representative mono- and dialkylboranes as thexylborane and dicyclohexylborane, followed by an oxidative workup, yields the corresponding beta-amino alcohols in good to excellent isolated yields. The hydroboration of ketone and aldehyde enamines with the asymmetric hydroboration reagents monoisopinocampheylborane ((d)IpcBH(2)) and diisopinocampheylborane ((d)Ipc(2)BH) was also investigated, (d)Ipc(2)BH is highly effective for the asymmetric hydroboration of acyclic aldehyde enamines, such as 1-(4-morpholino)-3-phenyl-1-propene and 1-(1-pyrrolidino)-1-octene. Oxidation of the intermediate trialkylborane furnishes the corresponding beta-amino alcohols in 50-86% ee. The stereogenic center of the carbinol carbon is consistently enriched in the R-enantiomer when (d)Ipc(2)BH prepared from (+)-alpha-pinene is used as the hydroboration reagent. The enantiomeric excesses of the beta-amino alcohols synthesized in this study were determined by HPLC using a chiral stationary phase. The absolute configurations of some of the beta-amino alcohols synthesized in this study were determined by chiral HPLC comparison with authentic beta-amino alcohols prepared from chiral epoxides of known absolute configuration.

  DOI：

  10.1021/jo00112a026

文献信息

• Synthesis of tetrafluoroethyl- and tetrafluoroethylene-containing amines by the reaction of silanes with enamines under acidic conditions
  作者：Yana Chernykh、Bronislav Jurásek、Petr Beier

  DOI：10.1016/j.jfluchem.2014.08.004

  日期：2015.3

  Enamines with in situ formed hydrogen fluoride underwent efficient reaction with trimethyl(1,1,2,2-tetrafluoro-2-(phenylthio)ethyl)silane and trimethyl(1,1,2,2-tetrafluoro-2-(phenylsulfonyl)ethyl)silane. Radical or reductive desulfurization of the addition products provided amines containing the tetrafluoroethyl group.

  原位形成氟化氢的烯胺与三甲基（1,1,2,2-四氟-2-（苯硫基）乙基）硅烷和三甲基（1,1,2,2-四氟-2-（苯磺酰基）乙基）有效反应）硅烷。加成产物的自由基或还原脱硫得到含有四氟乙基的胺。
• Asymmetric synthesis of .beta.-amino alcohols from chiral or achiral
  申请人：The Regents of the University of California

  公开号：US05367073A1

  公开（公告）日：1994-11-22

  The present invention relates to a process for the synthesis of chiral enantiomerically pure .beta.-amino alcohols which are extraordinarily important as therapeutic agents for the treatment of a variety of human disorders and as chiral auxiliaries in organic synthesis. The hydroboration of enamines is a versatile and convenient method for the synthesis of both racemic and enantiomerically pure .beta.-amino alcohols in high yields. This methodology enables the synthesis of virtually any .beta.-amino alcohol. Hydroboration of these enamines with chiral organic borohydrides, e.g. either mono- or diisopinocampheylborane, followed by oxidation with aqueous or solid NaOH/30% H.sub.2 O.sub.2 or Me.sub.3 NO, gives the corresponding chiral .beta.-amino alcohol. Enantiomeric excesses ranged from 60% for reactions run at 25.degree. C. to greater than 99% for reactions run at -25.degree. C.

  本发明涉及一种合成手性对映纯的β-氨基醇的方法，这些β-氨基醇作为治疗多种人类疾病的治疗剂和有机合成中手性辅助剂具有非常重要的意义。烯胺的氢硼化是一种多用途、方便的合成方法，可高产率地合成混合和手性对映纯的β-氨基醇。该方法使得几乎任何β-氨基醇都可以合成。使用手性有机硼氢化物（例如单或双异丙基蒎硼烷）对这些烯胺进行氢硼化，然后用水溶性或固体NaOH / 30％ H2O2或Me3NO氧化，得到相应的手性β-氨基醇。对映体过量范围从在25℃下反应时为60％到在-25℃下反应时大于99％。
• Convenient conversion of aldehydes and ketones into the corresponding alkenes via hydroboration of their enamines. A remarkably simple synthesis of either (Z)- or (E)-alkenes
  作者：Bakthan Singaram、Christian T. Goralski、Milind V. Rangaishenvi、Herbert C. Brown

  DOI：10.1021/ja00183a068

  日期：1989.1
• GORALSKI, CH. T.;SINGARAM, B.;BROWN, H. C., J. ORG. CHEM., 52,(1987) N 18, 4014-4019
  作者：GORALSKI, CH. T.、SINGARAM, B.、BROWN, H. C.

  DOI：——

  日期：——
• US5367073A
  申请人：——

  公开号：US5367073A

  公开（公告）日：1994-11-22