1-[(S)-[(2S,6R)-2-methyl-6-propylpiperidyl]phenylmethyl]-2-naphthalenol | 848302-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(S)-[(2S,6R)-2-methyl-6-propylpiperidyl]phenylmethyl]-2-naphthalenol
• 英文别名: 1-[(S)-[(2S,6R)-2-methyl-6-propylpiperidin-1-yl]-phenylmethyl]naphthalen-2-ol
• CAS: 848302-37-4
• 化学式: C₂₆H₃₁NO
• 分子量: 373.538
• InChiKey: YRMINRJYGQWINV-WSNOQYBDSA-N

物化性质

• 沸点：
  505.5±35.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  1-[(S)-[(2S,6R)-2-methyl-6-propylpiperidyl]phenylmethyl]-2-naphthalenol 在 1,1,2-三氯乙烷 、 10% palladium on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.17h， 以97%的产率得到(2S,6R)-dihydropinidine hydrochloride
  参考文献：
  名称：

  Highly Chemoselective Pd−C Catalytic Hydrodechlorination Leading to the Highly Efficient N-Debenzylation of Benzylamines

  摘要：

  In the presence of 1,1,2-trichloroethane, a novel procedure for the Pd-C catalytic N-debenzylation of benzylamines was established. The method proceeded in a synergistic catalytic system and directly gave the products as crystal amine hydrochlorides in practically quantitative yields.

  DOI：

  10.1021/jo9007282
• 作为产物：
  描述：

  (7aR,11R,13S)-11-(1H-benzotriazol-1-yl)-7a,8,10,11-tetrahydro-13-phenyl-9H,13H-naphtho[1,2-e]pyrido[2,1-b][1,3]oxazine 在 magnesium 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 1-[(S)-[(2S,6R)-2-methyl-6-propylpiperidyl]phenylmethyl]-2-naphthalenol
  参考文献：
  名称：

  Nonracemic Betti Base as a New Chiral Auxiliary:  Application to Total Syntheses of Enantiopure (2S,6R)-Dihydropinidine and (2S,6R)-Isosolenopsins

  摘要：

  Total syntheses of enantiopure alkaloidal natural products (2S,6R)-dihydropinidine (as hydrochloride) and (2S,6R)isosolenopsins (as hydrochlorides) were achieved in four steps and in 80-82% total yields by using a synthetic strategy of the formation-cleavage of 1,3-oxazinane. (S)-Betti base was proved to be an excellent chiral auxiliary and a novel Pd/C catalyzed N-debenzylation straightforward to amine hydrochloride was developed in the presence of CH2Cl2.

  DOI：

  10.1021/jo0480444

文献信息

• Nonracemic Betti Base as a New Chiral Auxiliary:  Application to Total Syntheses of Enantiopure (2<i>S</i>,6<i>R</i>)-Dihydropinidine and (2<i>S</i>,6<i>R</i>)-Isosolenopsins
  作者：Xinyan Wang、Yanmei Dong、Jianwei Sun、Xuenong Xu、Rui Li、Yuefei Hu

  DOI：10.1021/jo0480444

  日期：2005.3.1

  Total syntheses of enantiopure alkaloidal natural products (2S,6R)-dihydropinidine (as hydrochloride) and (2S,6R)isosolenopsins (as hydrochlorides) were achieved in four steps and in 80-82% total yields by using a synthetic strategy of the formation-cleavage of 1,3-oxazinane. (S)-Betti base was proved to be an excellent chiral auxiliary and a novel Pd/C catalyzed N-debenzylation straightforward to amine hydrochloride was developed in the presence of CH2Cl2.
• Highly Chemoselective Pd−C Catalytic Hydrodechlorination Leading to the Highly Efficient <i>N</i>-Debenzylation of Benzylamines
  作者：Chuanjie Cheng、Jianwei Sun、Lixin Xing、Jimin Xu、Xinyan Wang、Yuefei Hu

  DOI：10.1021/jo9007282

  日期：2009.8.7

  In the presence of 1,1,2-trichloroethane, a novel procedure for the Pd-C catalytic N-debenzylation of benzylamines was established. The method proceeded in a synergistic catalytic system and directly gave the products as crystal amine hydrochlorides in practically quantitative yields.