(anthracen-9-ylmethoxy)(tert-butyl)dimethylsilane | 918161-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (anthracen-9-ylmethoxy)(tert-butyl)dimethylsilane
• 英文别名: [(Anthracen-9-YL)methoxy](tert-butyl)dimethylsilane；anthracen-9-ylmethoxy-tert-butyl-dimethylsilane
• CAS: 918161-50-9
• 化学式: C₂₁H₂₆OSi
• 分子量: 322.522
• InChiKey: BKRFSRVHNSODMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (anthracen-9-ylmethoxy)(tert-butyl)dimethylsilane 在 iron(III) chloride 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  New chiral 1,2-aminoalcohols derived from biomass and their application in diethyl zinc additions

  摘要：

  A convenient procedure for the preparation of chiral 1,2-aminoalcohols starting from levoglucosenone, a biomass derivative, is described. The 1,2-aminoalcohols, bearing primary, secondary, and tertiary amino groups, were tested as chiral catalysts in the asymmetric addition of diethyl zinc to benzaldehyde. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.124
• 作为产物：
  描述：

  9-蒽醇 、 叔丁基二甲基氯硅烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 以98%的产率得到(anthracen-9-ylmethoxy)(tert-butyl)dimethylsilane
  参考文献：
  名称：

  9-取代的蒽与左旋葡萄糖醛酮之间的微波辅助区域选择性环加成反应。

  摘要：

  在微波辐射和常规加热条件下，研究了9-取代的蒽与左旋葡糖酮的环加成反应。考虑到时间，产量和区域选择性，微波技术已被证明是实现这种化学转化的理想工具。[反应：请参见文字]。

  DOI：

  10.1021/ol062254g

文献信息

• Microwave-Assisted Regioselective Cycloaddition Reactions between 9-Substituted Anthracenes and Levoglucosenone
  作者：Ariel M. Sarotti、Madeleine M. Joullié、Rolando A. Spanevello、Alejandra G. Suárez

  DOI：10.1021/ol062254g

  日期：2006.11.1

  The cycloaddition reactions of 9-substituted anthracenes and levoglucosenone were investigated under microwave irradiation and conventional heating conditions. Considering time, yields, and regioselectivity, microwave technology has proven to be an ideal tool to achieve this chemical transformation. [reaction: see text].

  在微波辐射和常规加热条件下，研究了9-取代的蒽与左旋葡糖酮的环加成反应。考虑到时间，产量和区域选择性，微波技术已被证明是实现这种化学转化的理想工具。[反应：请参见文字]。
• Second generation levoglucosenone-derived chiral auxiliaries. Scope and application in asymmetric Diels–Alder reactions
  作者：Ariel M. Sarotti、Rolando A. Spanevello、Alejandra G. Suárez

  DOI：10.1016/j.tet.2009.02.020

  日期：2009.4

  Chiral alcohols were designed and easily prepared from levoglucosenone, a biomass-derived valuable synthon. These alcohols were tested as chiral auxiliaries in asymmetric Diels-Alder reactions between the corresponding acrylates with acyclic and cyclic dienes. The regio, stereo, and facial selectivity varied from very good to excellent, depending upon the benzylic substitution of the auxiliary and the diene employed. As a consequence, after removal of the auxiliary, the resulting carboxylic acid derivatives were obtained in 72-99% ee. (C) 2009 Elsevier Ltd. All rights reserved.
• Development of polymer-supported chiral aminoalcohols derived from biomass and their application to asymmetric alkylation
  作者：María C. Botta、Hernán D. Biava、Rolando A. Spanevello、Ernesto G. Mata、Alejandra G. Suárez

  DOI：10.1016/j.tetlet.2016.04.021

  日期：2016.5

  starting from easily available and renewable chiral building blocks. They were tested as chiral ligands for the asymmetric diethylzinc addition to carbonyl compounds. Enantioselectivities were comparable to those observed for non-immobilized analogs. These results provide strong evidence for the flexibility of our approach to generate highly valuable supported chiral ligands derived from cellulose-rich materials

  已经开发了一种合成策略，用于从易于获得和可再生的手性建筑原料开始制备固定的1,2-氨基醇。将它们作为羰基化合物不对称二乙基锌的手性配体进行了测试。对映选择性与未固定类似物观察到的相当。这些结果为我们的方法的灵活性提供了有力的证据，该方法可用于从富含纤维素的材料中生成高度有价值的负载型手性配体。
• New chiral 1,2-aminoalcohols derived from biomass and their application in diethyl zinc additions
  作者：María M. Zanardi、María C. Botta、Alejandra G. Suárez

  DOI：10.1016/j.tetlet.2014.08.124

  日期：2014.10

  A convenient procedure for the preparation of chiral 1,2-aminoalcohols starting from levoglucosenone, a biomass derivative, is described. The 1,2-aminoalcohols, bearing primary, secondary, and tertiary amino groups, were tested as chiral catalysts in the asymmetric addition of diethyl zinc to benzaldehyde. (C) 2014 Elsevier Ltd. All rights reserved.