(R)-Betti base (-)-tartaric acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-Betti base (-)-tartaric acid
• 英文别名: 1-[(R)-amino(phenyl)methyl]naphthalen-2-ol;(2S,3S)-2,3-dihydroxybutanedioic acid
• 化学式: C₄H₆O₆*C₁₇H₁₅NO
• 分子量: 399.4
• InChiKey: SFGQEHBXKVZEEH-RSJGWRKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  161
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-Betti base (-)-tartaric acid 在 lithium aluminium tetrahydride 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 phosphate buffer 、 乙醇 为溶剂， 反应 2.0h， 生成 (R)-1-(α-azepanylbenzyl)-2-naphthol
  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
• 作为产物：
  描述：

  1-[氨基(苯基)甲基]-2-萘酚 在 硫酸 、 三乙胺 作用下， 以 水 、 丙酮 为溶剂， 反应 7.0h， 生成 (R)-Betti base (-)-tartaric acid
  参考文献：
  名称：

  An Efficient Kinetic Resolution of Racemic Betti Base Based on an Enantioselective N,O-Deketalization

  摘要：

  [GRAPHIC]An efficient kinetic resolution of racemic Betti base with L-(+)-tartaric acid in acetone was developed based on a novel enantioselective N,O-deketalization, by which the enantiopure R- and S-enantiomers of Betti base were obtained as the corresponding NO-ketal compound and salt with L-(+)-tartaric acid, respectively, in excellent yields with a practically foolproof operation.

  DOI：

  10.1021/jo051328j

文献信息

• Preparation of Enantiopure Substituted Piperidines Containing 2-Alkene or 2-Alkyne Chains: Application to Total Syntheses of Natural Quinolizidine-Alkaloids
  作者：Guolin Cheng、Xinyan Wang、Deyong Su、Hui Liu、Fei Liu、Yuefei Hu

  DOI：10.1021/jo902615u

  日期：2010.3.19

  nonracemic Betti base as a chiral auxiliary. The key step is that the auxiliary residue was removed by a novel base-catalyzed N-debenzylation via a formation of o-quinone methide mechanism in stead of the traditional hydrogenolysis, by which the alkene or alkyne groups survived. By this method, ten 2-alkene- or 2-alkyne-containing chain substituted piperidines were prepared on the gram scale within

  通过使用非外消旋的Betti碱作为手性助剂，建立了制备对映体纯的含2个烯烃或2个炔烃的链取代哌啶的一般方法。关键步骤是代替传统的氢解反应，通过传统的氢解反应，通过邻甲基苯甲酸甲酯的形成，通过新颖的碱催化的N-脱苄基反应去除了辅助残基。通过这种方法，在数小时内以克为单位制备了十个含2-烯烃或2-炔烃的链取代的哌啶。为了证明该方法的有效性和产品的多功能性，使用（S）-2-烯丙基完成了天然生物碱（+）-peltierine，（-）-lasubine II和（+）-cermizine C的总合成--N -Boc-哌啶为通用成分。
• An Efficient Kinetic Resolution of Racemic Betti Base Based on an Enantioselective <b><i>N</i></b>,<b><i>O</i></b>-Deketalization
  作者：Yanmei Dong、Rui Li、Jun Lu、Xuenong Xu、Xinyan Wang、Yuefei Hu

  DOI：10.1021/jo051328j

  日期：2005.10.1

  [GRAPHIC]An efficient kinetic resolution of racemic Betti base with L-(+)-tartaric acid in acetone was developed based on a novel enantioselective N,O-deketalization, by which the enantiopure R- and S-enantiomers of Betti base were obtained as the corresponding NO-ketal compound and salt with L-(+)-tartaric acid, respectively, in excellent yields with a practically foolproof operation.
• 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%。