dl-threo-2-(1-piperidino)-1,2-diphenylethanol | 19640-36-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: dl-threo-2-(1-piperidino)-1,2-diphenylethanol
• 英文别名: 1,2-Diphenyl-2-piperidin-1-ylethanol
• CAS: 19640-36-9
• 化学式: C₁₉H₂₃NO
• 分子量: 281.398
• InChiKey: ZGYPFPPCAPRYKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dl-threo-2-(1-piperidino)-1,2-diphenylethanol 在 N,N-二乙基(2-氯-1,1,2-三氟乙基)胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-(2-Fluoro-1,2-diphenyl-ethyl)-piperidine; hydrochloride
  参考文献：
  名称：

  合成和立体化学叔胺β-芴在氟代氨基醇类中的合成，有氟，1,1,2氯-2 N，N-二乙基乙胺（FAR）等，并混合有HF-吡啶。

  摘要：

  合成和立体化学研究了氨基醇的氟化，生成叔β-氟胺。初始和最终产物的构型使用1 H和19 F NMR进行分配。氨基醇与FAR的氟化反应是立体定向反应，保留了构型。可以得到异构或光学纯的化合物。用HF-吡啶混合物氟化可优先得到苏式氟胺。

  DOI：

  10.1016/s0022-1139(00)81971-5
• 作为产物：
  描述：

  1,2-二苯基-2-(1-哌啶基)乙酮 在 sodium borohydrid 作用下， 以 乙醇 、 水 为溶剂， 生成 dl-threo-2-(1-piperidino)-1,2-diphenylethanol
  参考文献：
  名称：

  1,2-diarylethylamines for treatment of neurotoxic injury

  摘要：

  公开号：

  EP0346791B1

文献信息

• Microwave-enhanced bismuth triflate-catalyzed epoxide opening with aliphatic amines
  作者：Thierry Ollevier、Etienne Nadeau

  DOI：10.1016/j.tetlet.2007.12.100

  日期：2008.2

  In the presence of a catalytic amount of Bi(OTf)3·4H2O and under microwave irradiation, neat mixtures of epoxides and amines afforded smoothly the corresponding 2-amino alcohols. A wide variety of aliphatic amines were reacted with cycloalkene oxide, styrene oxide, and stilbene oxide. The reaction proceeded rapidly and afforded the 2-amino alcohols in high up to quantitative yields. All products could

  在催化量的Bi（OTf）3 ·4H 2 O的存在下，在微波辐射下，环氧化物和胺的纯净混合物可平稳地得到相应的2-氨基醇。使多种脂族胺与环氧化烯，氧化苯乙烯和氧化二苯乙烯反应。反应进行得很快，并以高至定量的产率得到了2-氨基醇。通过简单过滤，无需水后处理即可获得所有产品。
• C-C Bond Fragmentation as a Probe for Photoinduced Intramolecular Electron Transfer
  作者：Yingsheng Wang、Lucian A. Lucia、Kirk S. Schanze

  DOI：10.1021/j100007a028

  日期：1995.2

  Photochemical and photophysical studies are reported for the complex, fac-(bpy)Re-I(CO)(3)(DA)(1+) (e-1), where bpy is 2,2'-bipyridine and DA is a ''reactive donor ligand'' that contains a vicinal diamine functionality. Photoexcitation of e-l into the dst (Re) --> pi* (bpy) metal-to-ligand charge transfer (MLCT) excited state leads to formation of the ligand-to-ligand charge transfer (LLCT) state, *(bpy(.-))Re-I(CO)(3)(DA(.+))(1+), via diamine ligand-to-Re electron transfer. In the LLCT state, the reactive donor ligand radical cation undergoes an exceedingly rapid heterolytic C-C bond fragmentation reaction to produce an iminium ion and an cr-amino radical fragment. Steady-state photochemical studies reveal that in air-saturated solution the only products observed arise from C-C bond fragmentation, which implies that under these conditions bond fragmentation is irreversible. Laser flash photolysis studies indicate that the a-amino radical that is produced by bond fragmentation in the LLCT state absorbs strongly in the near-UV region. A kinetic analysis is carried out under the assumptions that: (1) the quantum yield for formation the LLCT state can be derived from MLCT emission lifetime data on the diamine complex and a suitable non-donor-substituted model complex and (2) C-C bond fragmentation is irreversible. This analysis affords lower limits for the rates of back electron transfer and bond fragmentation (1.5 x 10(8) and 1.0 x 10(8) s(-1), respectively).
• Kinetics and mechanism of aliphatic amine oxidation by aqueous (batho)2CuII
  作者：Fengjiang Wang、Lawrence M. Sayre

  DOI：10.1021/ja00027a032

  日期：1992.1

  The kinetics of oxidation of a large series of aliphatic amines by the 'high-potential'' oxidant (batho)2Cu(II) (batho = 2,9-dimethyl-4,7-diphenyl-1,10-phenanthrolinedisulfonate) was studied under pseudo-first-order conditions (excess amine) in water or in 30% aqueous methanol (v/v) at 25-degrees-C over the pH range 7-11. The oxidations follow bell-shaped pH-rate profiles, with the low-pH leg reflecting the fact that only the free amine base is subject to oxidation and the high-pH leg representing conversion of (batho)2Cu(II) to an ineffective oxidant at high pH. The latter is thought to be (batho)Cu(II)(OH2)OH on the basis of the observed effect of [batho] on rate at high pH, and curve fitting of the rate data yielded estimates of the unitless K(eq) values governing this conversion. The variation in rate with degree of N-substitution and other structure-reactivity trends (such as the effect of ring size and the non-rate-retarding effect of 2,4,6-trimethyl substitution on PhCH2NR2) support a mechanism involving initial outer-sphere one-electron transfer, followed by proton transfer to the solvent, and then a rapid second one-electron oxidation to give imine/iminium product. Inner-sphere coordination of chelating amines shuts down the redox reaction, presumably as a consequence of displacement of the batho ligand(s) needed for high oxidant strength. Deuterium kinetic isotope effect (DKIE) measurements (i) comparing PhCD2N(CD3)2 vs PhCH2N(CH3)2 (intermolecular DKIE) and (ii) determining N-dealkylation preference in the case of PhCH2N(CH3)CD2Ph (intramolecular DKIE) suggest that the initial electron transfer is mainly rate-limiting. A rate comparison between erythro and three diastereomers of 1,2-diphenyl-2-piperidinoethanol indicates a stereoelectronic preference for one-electron oxidation at nitrogen when held antiperiplanar to a beta-hydroxyl. Stoichiometry studies using an excess of the Cu(II) oxidant reveal regioselective and chemoselective factors governing the overall amine-to-iminium oxidations.