(S)-1-(α-piperidylbenzyl)-2-naphthol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-(α-piperidylbenzyl)-2-naphthol
• 英文别名: (S)-1-(α-piperidinylbenzyl)-2-naphthol；1-[(S)-phenyl(piperidin-1-yl)methyl]naphthalen-2-ol
• 化学式: C₂₂H₂₃NO
• mdl: MFCD00098753
• 分子量: 317.431
• InChiKey: RJMSVDFLOXQKOO-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 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 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 (S)-1-(α-piperidylbenzyl)-2-naphthol
  参考文献：
  名称：

  Diastereopure Preparation of α-Benzotriazolyl 1-Azacycloalka[2,1-b][1,3]-oxazines and their Application as Versatile Chiral Precursors

  摘要：

  制备了一组非外消旋的贝蒂碱衍生的立体纯α-苯并三氮唑基1-氮杂环烷[2,1-b][1,3]恶嗪。这些化合物被用作制备手性配体和手性取代氮杂环化合物的前体，具有显著的立体选择性优势。

  DOI：

  10.1055/s-2003-43353
• 作为试剂：
  描述：

  diethylzinc 、 对氟苯甲醛 在 (S)-1-(α-piperidylbenzyl)-2-naphthol 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以96%的产率得到1-(4-氟苯基)-1-丙醇
  参考文献：
  名称：

  Novel preparation of non-racemic 1-[α-(1-azacycloalkyl)benzyl]-2-naphthols from Betti base and their application as chiral ligands in the asymmetric addition of diethylzinc to aryl aldehydes

  摘要：

  开发了一种制备非外消旋的1-[α-(1-氮杂环烷基)苯基]-2-萘醇的创新路线，该方法涉及在NaBH3CN的存在下对Betti碱进行区域选择性的N-环烷基化，与二醛反应生成1-氮杂环烷基[2,1-b]噁唑，随后用LiAlH4选择性断裂C–O键。作为一种新的手性配体家族，我们测试了其在二乙基锌对芳基醛进行对映选择性加成中的应用。结合呱啉和哌啶的配体实现了高效的非对称诱导，生成的产物收率高达96%，对映体过量（ee）达到99%。

  DOI：

  10.1039/b204534f

文献信息

• Diastereopure Preparation of α-Benzotriazolyl 1-Azacycloalka[2,1-<i>b</i>][1,3]-oxazines and their Application as Versatile Chiral Precursors
  作者：Yuefei Hu、Xuenong Xu、Jun Lu、Rui Li、Zongming Ge、Yanmei Dong

  DOI：10.1055/s-2003-43353

  日期：——

  A group of diastereopure α-benzotriazolyl 1-azacyclo­alka[2,1-b][1,3]oxazines were prepared from non-racemic Betti base and they were employed as the versatile precursors for the preparation of chiral ligands and chiral substituted azacyclics with significant advantages in the stereoselectivity.

  制备了一组非外消旋的贝蒂碱衍生的立体纯α-苯并三氮唑基1-氮杂环烷[2,1-b][1,3]恶嗪。这些化合物被用作制备手性配体和手性取代氮杂环化合物的前体，具有显著的立体选择性优势。
• Synthesis of chiral ligands derived from the Betti base and their use in the enantioselective addition of diethylzinc to aromatic aldehydes
  作者：Jun Lu、Xuenong Xu、Cunde Wang、Jiangang He、Yuefei Hu、Hongwen Hu

  DOI：10.1016/s0040-4039(02)01985-8

  日期：2002.11

  A novel procedure for selective direct N,N-alkylation of the chiral Betti base was developed, and a new family of chiral ligands, (S)-1-(α-cycloaminobenzyl)-2-naphthols, were prepared. The ligands with five- and six-membered cyclic amines showed highly efficient asymmetric induction in the addition of diethylzinc to aromatic aldehydes in 93–96% yields and 91–99% ee.

  提出了一种新的选择性手性Betti碱直接N，N-烷基化的方法，并制备了一个新的手性配体家族，即（S）-1-（α-环氨基苄基）-2-萘酚。具有五元和六元环胺的配体在芳族醛中添加二乙基锌以93–96％的收率和91–99％ee的情况下显示出高效的不对称诱导。
• Periasamy, Mariappan; Anwar, Shaik; Reddy, Meda Narsi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 9, p. 1261 - 1273
  作者：Periasamy, Mariappan、Anwar, Shaik、Reddy, Meda Narsi

  DOI：——

  日期：——
• THE RESOLUTION OF 1-(ALPHA-1-PIPERIDYLBENZYL)-2-NAPHTHOL¹
  作者：Wallace R. Brode、Joseph B. Littman

  DOI：10.1021/ja01375a062

  日期：1930.12
• Novel preparation of non-racemic 1-[α-(1-azacycloalkyl)benzyl]-2-naphthols from Betti base and their application as chiral ligands in the asymmetric addition of diethylzinc to aryl aldehydes
  作者：Jun Lu、Xuenong Xu、Shaozhong Wang、Cunde Wang、Yuefei Hu、Hongwen Hu

  DOI：10.1039/b204534f

  日期：——

  A novel route for the preparation of non-racemic 1-[α-(1-azacycloalkyl)benzyl]-2-naphthols was developed, which involves regioselective N-cycloalkylation of the Betti base with dials in the presence of NaBH3CN to give 1-azacycloalka[2,1-b]oxazine followed by the selective cleavage of a C–O bond with LiAlH4. As a new family of chiral ligands, their application in the enantioselective addition of diethylzinc to aryl aldehydes was tested. The ligands incorporating pyrrolidine and piperidine led to highly efficient asymmetric induction to give products in up to 96% yield and 99% ee.

  开发了一种制备非外消旋的1-[α-(1-氮杂环烷基)苯基]-2-萘醇的创新路线，该方法涉及在NaBH3CN的存在下对Betti碱进行区域选择性的N-环烷基化，与二醛反应生成1-氮杂环烷基[2,1-b]噁唑，随后用LiAlH4选择性断裂C–O键。作为一种新的手性配体家族，我们测试了其在二乙基锌对芳基醛进行对映选择性加成中的应用。结合呱啉和哌啶的配体实现了高效的非对称诱导，生成的产物收率高达96%，对映体过量（ee）达到99%。