(S)-1-(phenyl(pyrrolidin-1-yl)methyl)naphthalen-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-(phenyl(pyrrolidin-1-yl)methyl)naphthalen-2-ol
• 英文别名: (S)-(+)-1-(α-pyrrolidinylbenzyl)-2-naphthol；S(+)-1-(α-pyrrolidinyl benzyl)-2-napthol；(S)-1-(α-pyrrolidinylbenzyl)-2-naphthol；1-((S)-Phenyl(pyrrolidin-1-YL)methyl)naphthalen-2-OL；1-[(S)-phenyl(pyrrolidin-1-yl)methyl]naphthalen-2-ol
• 化学式: C₂₁H₂₁NO
• 分子量: 303.404
• InChiKey: VJIGXDICQFIIAM-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  (S)-1-(phenyl(pyrrolidin-1-yl)methyl)naphthalen-2-ol 在 copper(II) acetate monohydrate 作用下， 以 对二甲苯 为溶剂， 反应 2.0h， 生成 (7aR,12S)-12-phenyl-7a,8,9,10-tetrahydro-12H-naphtho[1,2-e]pyrrolo[2,1-b][1,3]oxazine 、 rac-(7aS,11R)-11-phenyl-7a,8,9,10-tetrahydro-11H-7-oxa-10a-aza-cyclopenta[b]phenanthrene
  参考文献：
  名称：

  铜催化叔胺的区域选择性分子内氧化α-官能化：二氢-1,3-恶嗪的高效合成

  摘要：

  交通控制：羟基官能团指导叔胺的α-官能化，通过CO键的形成合成1,3-恶嗪。与苄基和非苄基胺都发生反应。在萘并恶嗪合成的情况下，观察到100％的非对映选择性。对于该反应，提出了一种暂定的两种途径的机制。

  DOI：

  10.1002/anie.201304654
• 作为产物：
  描述：

  1-(phenyl(pyrrolidin-1-yl)methyl)naphthalen-2-ol 在 L-酒石酸 、 sodium carbonate 作用下， 以 丙酮 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 以40%的产率得到(S)-1-(phenyl(pyrrolidin-1-yl)methyl)naphthalen-2-ol
  参考文献：
  名称：

  Periasamy, Mariappan; Anwar, Shaik; Reddy, Meda Narsi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 9, p. 1261 - 1273

  摘要：

  DOI：

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 and resolution of 1-(α-pyrrolidinylbenzyl)-2-naphthol and its application in the resolution of 2,2′-dihydroxy-1,1′-binaphthyl
  作者：Mariappan Periasamy、Meda Narsi Reddy、Shaik Anwar

  DOI：10.1016/j.tetasy.2004.04.030

  日期：2004.6

  samples that can be readily purified to enantiomeric purity through preparation of hydrogen bonded aggregates. The homochiral 1-(α-pyrrolidinylbenzyl)-2-naphthol 2 is useful in the resolution of racemic 2,2′-dihydroxy-1,1′-binaphthyl (BINOL) 3 via preparation of the corresponding diastereomeric borate complexes using B(OH)3.

  使用苯甲醛，2-萘酚和吡咯烷在乙醇中的温度为78°C，可以轻松地以95％的产率制备1-（α-吡咯烷基苄基）-2-萘酚2。使用廉价的1-（+）-酒石酸将其拆分，即可获得非外消旋体样品，这些样品可通过制备氢键结合的聚集体轻松纯化至对映体纯度。的纯手性的1-（α-pyrrolidinylbenzyl）-2-萘酚2是外消旋2,2的分辨率有用' -二羟基- 1,1 '联萘（BINOL）3经由制备采用B相应的非对映体配合物的硼酸盐的（OH ）3。
• 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。
• 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%。
• Enantioselective Organocatalytic Three-Component Petasis Reaction among Salicylaldehydes, Amines, and Organoboronic Acids
  作者：Wen-Yong Han、Zhi-Jun Wu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1021/ol203109a

  日期：2012.2.17

  The catalytic enantioselective three-component Petasis reaction among salicylaldehydes, amines, and organoboronic acids with a newly designed thiourea-binol catalyst is presented. A broad range of alkylaminophenols can be obtained in good yield (up to 92%) and good to high enantioselectivity (up to 95% ee). A possible reaction pathway for this catalytic enantioselective Petasis reaction is tentatively proposed.