(2R,2'S)-(+)-2-phenyl-2-(2'-propyl-piperidin-1'-yl)-ethanol | 88056-96-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (2R,2'S)-(+)-2-phenyl-2-(2'-propyl-piperidin-1'-yl)-ethanol
• 英文别名: (2R,2'S)-(-)-2-phenyl-2-(2'-propylpiperidin-1'-yl)ethanol；(2R)-2-phenyl-2-[(2S)-2-propylpiperidin-1-yl]ethanol
• CAS: 88056-96-6
• 化学式: C₁₆H₂₅NO
• 分子量: 247.381
• InChiKey: AZACJMYSLMUYOE-HOTGVXAUSA-N

物化性质

• 沸点：
  356.5±22.0 °C(Predicted)
• 密度：
  1.011±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (2R,2'S)-(+)-2-phenyl-2-(2'-propyl-piperidin-1'-yl)-ethanol 在 palladium on activated charcoal 氢气 作用下， 以 盐酸 、 甲醇 为溶剂， 反应 15.0h， 生成 毒芹碱
  参考文献：
  名称：

  Chiral 1,4-dihydropyridine equivalents: a new approach to the asymmetric synthesis of alkaloids. The enantiospecific synthesis of (+)- and (-)-coniine and dihydropinidine

  摘要：

  DOI：

  10.1021/ja00364a053
• 作为产物：
  描述：

  (-)-2-氰-6-苯基恶唑哌啶 在 sodium tetrahydroborate 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 (2R,2'S)-(+)-2-phenyl-2-(2'-propyl-piperidin-1'-yl)-ethanol
  参考文献：
  名称：

  Chiral 1,4-dihydropyridine equivalents: a new approach to the asymmetric synthesis of alkaloids. The enantiospecific synthesis of (+)- and (-)-coniine and dihydropinidine

  摘要：

  DOI：

  10.1021/ja00364a053

文献信息

• New methodology for the synthesis of enantiopure (3R,2aR)-(−)-3-phenyl-hexahydro-oxazolo[3,2-a]-pyridin-5-one: a synthesis of (S)-(+)-coniine
  作者：J.L. Terán、D. Gnecco、A. Galindo、J. Juárez、S. Bernès、R.G. Enrı́quez

  DOI：10.1016/s0957-4166(01)00063-5

  日期：2001.3

  A new and efficient methodology for the enantiopure synthesis of (3R,2aR)-(−)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one 3 starting from (1′R)-(−)-1-(2′-hydroxy-1′-phenyl-ethyl)-(1H)-pyridin-2-one 1 is described. In addition, the enantiospecific synthesis of (S)-(+)-coniine hydrochloride 6 in good yield from 3 is reported.

  对于（3的对映体纯合成一个新的和有效的方法- [R，2A - [R - （ - ） - ）-3-苯基-六氢-恶唑并[3,2-一个]吡啶-5-酮3从（1'开始- [R ） -描述了（-）-1-（2'-羟基-1'-苯基-乙基）-（1 H）-吡啶-2-酮1。另外，报道了对映体特异性地从（3）以高收率合成（S）-（+）-可可碱盐酸盐6。
• Asymmetric synthesis. XL. 2,3-Disubstituted piperidines via chiral non-racemic lactams
  作者：Lauren Micouin、Jean-Charles Quirion、Henri-Philippe Husson

  DOI：10.1016/0040-4039(95)02307-0

  日期：1996.2

  Optically pure 2,3-cis-disubstituted piperidines 7a and 7b have been prepared from chiral lactams 2. The first step involves C-2 functionalization with Grigard reagent, then a diastereoselective reduction of resulting oxazolidines 5 furishes the desired piperidines 7.

  由手性内酰胺2制备了光学纯的2，3-顺式二取代的哌啶7a和7b。第一步涉及使用Grigard试剂对C-2进行功能化，然后对所得恶唑烷5进行非对映选择性还原，得到所需的哌啶7。
• Syntheses of pyridin-4-ylium chirons: applications in a synthesis of (+)-coniine
  作者：Luis F. Roa、Dino Gnecco、Alberto Galindo、Joel L. Terán、Sylvain Bernès

  DOI：10.1016/j.tetasy.2004.01.017

  日期：2004.3

  The compounds (3R,5S)-(+)-5-methyl-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium iodide 4 and (3R,5S)-(+)-5-n-propyl-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium iodide 5 were synthesized in two steps starting from the bicyclic thiolactam trans(3R,2aS)-(-)-5-thio-3-phenyl-2,3,6,7,8,2a-hexahydro-oxazolo[3,2-a]pyridine 1. In addition, starting from 5 an enantiospecific synthesis of (+)-coniine 7 was achieved. (C) 2004 Elsevier Ltd. All rights reserved.
• Preparation of (R)-(+)-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium bromide: synthesis of (S)-(+)-coniine, (R)-(-)-coniceine and (R)-(+)-anabasine
  作者：A CASTRO、J RAMIREZ、J JUAREZ、J TERAN、L OREA、A GALINDO、D GNECCO

  DOI：10.1016/s0385-5414(07)81205-6

  日期：2007.12.1

  We describe the transformation of (R)-(-)-1-(2'-hydroxy-1'-phenylethyl)piperidin-2-one 1 into (R)-(-)-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium bromide 2 using POBr3, Reduction of 2 with Red-Al at -78 degrees C gave (3R,8aR)-(-)-3-phenylbexahydro-2H-oxazolo[3,8-a]-pyridine 3 as a single diastereoisomer. The synthetic potential of these transformation is illustrated by the enantiopure synthesis of (S)-(+)-coniine, (R)-(-)-coniceine and (R)-(+)-anabasine.
• Chiral 1,4-dihydropyridine equivalents: a new approach to the asymmetric synthesis of alkaloids. The enantiospecific synthesis of (+)- and (-)-coniine and dihydropinidine
  作者：Luc Guerrier、Jacques Royer、David S. Grierson、Henri Philippe Husson

  DOI：10.1021/ja00364a053

  日期：1983.12