(1R)-1-(1,3-benzodioxol-5-yl)-3-phenylprop-2-yn-1-ol | 1005216-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (1R)-1-(1,3-benzodioxol-5-yl)-3-phenylprop-2-yn-1-ol
• CAS: 1005216-38-5
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: OKRGURAXKOJTBM-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  胡椒醛 、 苯乙炔 在 diethylzinc 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 22.0h， 生成 (1S)-1-(1,3-benzodioxol-5-yl)-3-phenylprop-2-yn-1-ol 、 (1R)-1-(1,3-benzodioxol-5-yl)-3-phenylprop-2-yn-1-ol
  参考文献：
  名称：

  对映体纯N-（二茂铁基甲基）氮杂环丁烷-2-基（二苯基）甲醇催化有机锌试剂不对称加成到醛上的评估

  摘要：

  从廉价且容易获得的1 -（+）-甲硫氨酸开发了一种简便实用的对映体纯的N-（二茂铁基甲基）氮杂环丁烷-2-基（二苯基）甲醇的制备方法。合成亮点包括手性氮杂环丁烷环的三步，一锅结构和一种改进的单步过程为关键中间体的合成的发展升-2-氨基-4-溴丁酸。对映纯N评估了-（二茂铁基甲基）氮杂环丁烷-2-基（二苯基）甲醇催化有机锌试剂向醛的催化不对称加成。在催化量的手性氮存在下，醛的不对称乙基化，甲基化，芳基化和炔基化分别实现了高达98.4％，94.1％，99.0％和84.6％ee的对映选择性。-（二茂铁基甲基）氮杂环丁烷-2-基（二苯基）甲醇。我们的结果进一步证明，基于四元杂环的骨架是催化不对称诱导反应的良好潜在手性单元，与苯基相比，笨重的二茂铁基的阻碍在对映选择性中发挥了重要作用。基于包括两个HOAc分子的手性配体3b的晶体结构和先前的研究，已经提出了催化不对称加成的可能过渡。

  DOI：

  10.1021/jo701943x

文献信息

• Enantioselective addition of alkynylzinc to arylaldehydes catalyzed by azetidino amino alcohols bearing an additional stereogenic center
  作者：Jun-Long Niu、Min-Can Wang、Liu-jie Lu、Guo-Liang Ding、Hui-Jie Lu、Qing-Tao Chen、Mao-Ping Song

  DOI：10.1016/j.tetasy.2009.10.031

  日期：2009.11

  Chiral azetidino amino alcohol ligands bearing an additional stereogenic center were readily prepared and used as catalysts for the asymmetric addition of alkynylzinc to aromatic aldehydes with enantioselectivities of up to 87% ee. The relationship between the reaction enantioselectivity and the structure of the chiral ligands was also evaluated in this reaction. The experimental results showed that the enantioselectivity level of the reaction was greatly influenced by the second stereogenic center attached to azetidine ring, but the stereochemical sense was only determined by the configuration of the azetidine ring. A possible transition structure for the catalytic asymmetric addition was also proposed. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of new Schiff base-camphorsulfonyl amide ligands and in situ screening in the asymmetric additions of organozinc reagents to aldehydes
  作者：Jiangtao Sun、Xu Pan、Zhenya Dai、Chengjian Zhu

  DOI：10.1016/j.tetasy.2008.10.017

  日期：2008.11

  We have designed and synthesized a new library of highly modular Schiff base-camphorsulfonyl amide ligands from readily available starting materials. These ligands have been used in the asymmetric addition of diethyl zinc to aldehydes in good yields (up to 91%) and high enantioselectivities (up to 93%). Moreover, when the ligands were used in the asymmetric addition of phenylacetylene to aldehydes, good yields and moderate to high ee values (up to 90%) were obtained. The introduction of the camphorsulfonyl moiety into the ligands is highly critical for the selectivities of the reactions. Published by Elsevier Ltd.