threo-2-piperidino-1,2-diphenylethanol

• 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: threo-2-piperidino-1,2-diphenylethanol
• 英文别名: rac-1,2-diphenyl-2-(piperidin-1-yl)ethan-1-ol；threo-α'-Piperidino-bibenzyl-α-ol；(1S,2S)-1,2-diphenyl-2-piperidin-1-ylethanol
• 化学式: C₁₉H₂₃NO
• 分子量: 281.398
• InChiKey: ZGYPFPPCAPRYKE-OALUTQOASA-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：

  threo-2-piperidino-1,2-diphenylethanol 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以71%的产率得到rac-1-(2-chloro-1,2-diphenylethyl)piperidine
  参考文献：
  名称：

  氟化钾的氢键相转移催化：β-氟胺的对映选择性合成

  摘要：

  氟化钾 (KF) 是一种理想的氟化试剂，因为它安全、易于处理且成本低。然而，在有机溶剂中溶解度差，加上控制其反应性的策略有限，阻碍了其用于不对称 CF 键的形成。在这里，我们证明了使用 KF 的氢键相转移催化可以高产率和对映选择性获得有价值的 β-氟胺。该方法采用手性 N-乙基双脲催化剂，将固体 KF 作为三配位的脲-氟化物络合物带入溶液中。这种操作简单的反应使用 0.5 mol% 的可回收双脲催化剂提供了对映体富集的氟联苯胺（高达 50 g 规模）。

  DOI：

  10.1021/jacs.8b12568
• 作为产物：
  描述：

  2-溴-2-苯基乙酰苯 在 乙醚 、 aluminum isopropoxide 、 异丙醇 作用下， 生成 threo-2-piperidino-1,2-diphenylethanol
  参考文献：
  名称：

  Analgesics. III. Hydrochlorides of Phenylalkylamines

  摘要：

  DOI：

  10.1021/ja01177a080

文献信息

• Planar Chiral PHANOLs as Double Hydrogen Bonding Donor Organocatalysts: Synthesis and Catalysis
  作者：D. Christopher Braddock、Iain D. MacGilp、Benjamin G. Perry

  DOI：10.1002/adsc.200404065

  日期：2004.8

  4,12-Dihydroxy[2.2]paracyclophanediol (PHANOL; 1), and its para-substituted derivatives 2, 5 and 7, were found to catalyse Diels–Alder cycloadditions of α,β-unsaturated aldehydes or ketones with dienes and/or epoxide ring opening reactions with amines. The mode of catalysis by the PHANOLs is via double hydrogen bonding to the two sp2 lone pairs of a carbonyl group or the two lone pairs of the epoxide

  发现4,12-二羟基[2.2]对环庚二醇（PHANOL; 1）及其对位取代的衍生物2、5和7可以催化α，β-不饱和醛或酮与二烯和/或环氧化物的狄尔斯-阿尔德环加成反应与胺的开环反应。PHANOLs的催化方式是通过氢键与羰基的两个sp 2孤对或环氧化物的两个孤对进行双氢键合。该PHANOLs的Diels-Alder反应的催化活性的顺序基本上与基于的吸电子基团的能力（一个或多个）的程度在预期的氢键供体强度相关的对位置。相反，由于对双氢键模式的空间干扰，邻位取代的PHANOL 10、11和14没有活性作为催化剂。为支持所提出的双氢键模式，讨论了各种PHANOL的1 H NMR和IR光谱数据。
• Secondary and Tertiary Amino Ketones and Alcohols Derived from Desoxybenzoin and 1,2-Diphenylethanol.¹ Ring-Chain Tautomerism of the α-(β-Hydroxyethylamino) Ketones²
  作者：Robert E. Lutz、James A. Freek、Robert S. Murphey

  DOI：10.1021/ja01186a012

  日期：1948.6
• Isomeric Amino Alcohols from the Reaction of Styrene Oxide with Benzylamine
  作者：Colin L. Browne、Robert E. Lutz

  DOI：10.1021/jo50009a002

  日期：1952.9
• Photochemistry of Intramolecular Charge Transfer Excited States in Donor-Acceptor-Substituted Diamines
  作者：Yingsheng Wang、Kirk S. Schanze

  DOI：10.1021/j100018a019

  日期：1995.5

  The photochemistry and photophysics of 1,2-diamines C(5)H(10)NCHPhCHPhNHC(6)H(4)R (1, R = CN, and 2, R = 4-pyridyl) have been examined. These compounds display a strong absorption band in the near-UV which is due to intramolecular charge transfer from the secondary amine group to the 4-cyanophenyl or (4-pyridyl)phenyl acceptor unit. Photoexcitation into this absorption band leads to moderately intense fluorescence from the (1)LE state of the charge transfer chromophore and to homolytic bond fragmentation across the 1,2 C-C bond with moderate quantum efficiency. Detailed photochemical and photophysical studies reveal that the bond fragmentation reaction ensues from a second intramolecular charge transfer excited state (denoted (CT)-C-1) which is based on electron transfer from the tertiary piperidine nitrogen to the 4-cyanophenyl or (4-pyridyl)phenyl unit. Photochemical product analysis reveals that erythro --> three (or three --> erythro) isomerization occurs under both argon-degassed and air-saturated conditions. This observation indicates that recombination of the radicals formed by bond fragmentation occurs, both within the geminate pair and between free radicals that have escaped the solvent cage. Analysis of fluorescence, transient absorption, and steady-state photochemical kinetics data indicates that (1) internal conversion from the (1)LE state to the (CT)-C-1 state by intramolecular electron transfer occurs with k greater than or equal to 10(9) s(-1) in all of the diamines; (2) bond fragmentation within the (CT)-C-1 state occurs with k greater than or equal to 10(8) s(-1) in each of the diamines: (3) bond fragmentation may be faster in erythro-1 than in threo-1.
• Analgesics. III. Hydrochlorides of Phenylalkylamines
  作者：L. H. Goodson、R. B. Moffett

  DOI：10.1021/ja01177a080

  日期：1949.9