(4S,5S)-4,5-bis(di([1,1'-biphenyl]-4-yl)(azido)methyl)-2,2-dimethyl-1,3-dioxolane | 1442686-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S,5S)-4,5-bis(di([1,1'-biphenyl]-4-yl)(azido)methyl)-2,2-dimethyl-1,3-dioxolane
• CAS: 1442686-88-5
• 化学式: C₅₅H₄₄N₆O₂
• 分子量: 820.993
• InChiKey: JJCVFIMHUVUECM-YWSWRHJRSA-N

物化性质

• 熔点：
  142.1-143.9 °C

计算性质

• 辛醇/水分配系数(LogP)：
  14.68
• 重原子数：
  63.0
• 可旋转键数：
  12.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  115.98
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4,5-bis(di([1,1'-biphenyl]-4-yl)(azido)methyl)-2,2-dimethyl-1,3-dioxolane 在 lithium aluminium tetrahydride 、 potassium carbonate 、 copper(l) chloride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 11.17h， 生成
  参考文献：
  名称：

  Development of Tartaric Acid Derived Chiral Guanidines and Their Application to Catalytic Enantioselective α-Hydroxylation of β-Dicarbonyl Compounds

  摘要：

  A novel library of chiral guanidines featuring a tartaric acid skeleton was developed from diethyl L-tartrate. These guanidines are easily accessed with tunable style and electronic properties. The utilities of the guanidines were highlighted by their ability to catalyze the alpha-hydroxylation of beta-ketoesters and beta-diketones with remarkable efficiency and excellent enantioselectivity.

  DOI：

  10.1021/ol401306h
• 作为产物：
  描述：

  溴苯 在 氯化亚砜 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 75.0h， 生成 (4S,5S)-4,5-bis(di([1,1'-biphenyl]-4-yl)(azido)methyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Development of Tartaric Acid Derived Chiral Guanidines and Their Application to Catalytic Enantioselective α-Hydroxylation of β-Dicarbonyl Compounds

  摘要：

  A novel library of chiral guanidines featuring a tartaric acid skeleton was developed from diethyl L-tartrate. These guanidines are easily accessed with tunable style and electronic properties. The utilities of the guanidines were highlighted by their ability to catalyze the alpha-hydroxylation of beta-ketoesters and beta-diketones with remarkable efficiency and excellent enantioselectivity.

  DOI：

  10.1021/ol401306h

文献信息

• Metal-Free Azidation of α-Hydroxy Esters and α-Hydroxy Ketones Using Azidotrimethylsilane
  作者：Xiao-Ping Yin、Lei Zhu、Jian Zhou

  DOI：10.1002/adsc.201701345

  日期：2018.3.20

  We herein report a commercially available perchloric acid catalyst capable of catalyzing the azidation of α‐hydroxy esters, α‐hydroxy ketones and taddols using azidotrimethylsilane in dichloromethane at room temperature. Various substituted tertiary alcohols are well tolerated in this reaction. Cα‐tetrasubstituted α‐amino acid derivatives were prepared by one‐pot sequential azidation and hydrogenation

  我们在此报告了一种可商购的高氯酸催化剂，它能够在室温下在二氯甲烷中使用叠氮三甲基硅烷催化α-羟基酯，α-羟基酮和他达醇的叠氮化。在该反应中，各种取代的叔醇具有良好的耐受性。Ç α -tetrasubstitutedα氨基酸衍生物通过一锅顺序叠氮化和氢化方法制备。这种新开发的方法的优势包括操作简便，催化剂容易获得，规模放大能力以及良好的官能团兼容性。
• 基于手性二胺的螺环骨架的手性磷腈催化剂、 制备方法及其应用
  申请人：中国科学院上海有机化学研究所

  公开号：CN105056991B

  公开（公告）日：2017-06-13

  本发明提供一类基于手性二胺的螺环骨架的手性磷腈催化剂,制备方法以及应用。该催化剂具有(RX‑)3P＝NR’的通式结构，通过R，R’引入手性基团，具有两个七元环通过螺膦中心相连的结构。系利用旋光纯的酒石酸或取代的环己(戊)二酸作为原料，通过酯化，格式反应，有或无氯化反应，叠氮化反应，还原反应生成手性二胺，然后与五氯化磷发生螺环化反应构建膦中心螺环，在碱性条件下得到手性磷腈分子催化剂，其中直接的叠氮取代羟基的方法，具有很好的应用推广价值。该催化剂具有催化效率高、立体选择性好、条件温和、经济环保和操作简便等优点，具有推广和应用前景。
• Design of Highly Stable Iminophosphoranes as Recyclable Organocatalysts: Application to Asymmetric Chlorinations of Oxindoles
  作者：Xing Gao、Jianwei Han、Limin Wang

  DOI：10.1021/acs.orglett.5b02323

  日期：2015.9.18

  A new family of tartaric acid derived chiral iminophosphoranes has been developed as highly effective organocatalysts in the asymmetric chlorinations of 3-substituted oxindoles with a high level of enantioselectivity. Importantly, these catalysts are air- and moisture-stable. Recovery of the catalyst after simple chromatographic separation for reuse in the model reaction was achieved; the catalyst can be recycled six times without loss of any enantioselectivity. Several advantages of this catalytic process are high conversion after a very short reaction time at ambient temperature, low catalytic loading, and scale-up to multigram quantities with an excellent enantiomeric excess value of >99%, which meets the enantiomeric purity required for pharmaceutical purposes.