tert-butyl bethyl allyliminodicarbonate | 68819-86-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: tert-butyl bethyl allyliminodicarbonate
• 英文别名: tert-butyl N-methoxycarbonyl-N-prop-2-enylcarbamate
• CAS: 68819-86-3
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: JAOMBAPEXGAAOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl bethyl allyliminodicarbonate 、 p-chlorobenzenediazonium tetrafluoroborate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium acetate 作用下， 以 苯甲腈 为溶剂， 生成 (E)-tert-butyl methyl [3-(4-chlorophenyl)prop-2-en-1-yl]imidodicarbonate
  参考文献：
  名称：

  Substrate-Directable Heck Reactions with Arenediazonium Salts. The Regio- and Stereoselective Arylation of Allylamine Derivatives and Applications in the Synthesis of Naftifine and Abamines

  摘要：

  The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the carbonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.

  DOI：

  10.1021/jo201105z
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 咪唑 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.25h， 生成 tert-butyl bethyl allyliminodicarbonate
  参考文献：
  名称：

  Substrate-Directable Heck Reactions with Arenediazonium Salts. The Regio- and Stereoselective Arylation of Allylamine Derivatives and Applications in the Synthesis of Naftifine and Abamines

  摘要：

  The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the carbonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.

  DOI：

  10.1021/jo201105z

文献信息

• Evaluation of Kilogram-Scale Sonagashira, Suzuki, and Heck Coupling Routes to Oncology Candidate CP-724,714
  作者：David H. Brown Ripin、Dennis E. Bourassa、Thomas Brandt、Michael J. Castaldi、Heather N. Frost、Joel Hawkins、Phillip J. Johnson、Stephen S. Massett、Karin Neumann、James Phillips、Jeffery W. Raggon、Peter R. Rose、Jennifer L. Rutherford、Barbara Sitter、A. Morgan Stewart、Michael G. Vetelino、Lulin Wei

  DOI：10.1021/op050039u

  日期：2005.7.1

  The synthesis of the anti-cancer compound 2-methoxy-N-(3-4-[3-methyl-4-(6-methyl-pyridin-3-yloxy)phenylamino]quinazolin-6-yl}-E-allyl)acetamide (CP-724,714) (1) on multikilogram scale using several different synthetic routes is described. Application of the Sonogashira, Suzuki, and Heck couplings to this synthesis was investigated to identify a safe, environmentally friendly, and robust process for the production of this drug candidate. A convergent and selective synthesis of the candidate was identified which utilizes a Heck coupling of a protected allylamine to install the critical olefin.
• Clarke,C.T. et al., Journal of the Chemical Society. Perkin transactions I, 1978, p. 1088 - 1090
  作者：Clarke,C.T. et al.

  DOI：——

  日期：——
• CLARKE C.T.; ELLIOTT J. D.; JONES J. H., J. CHEM. SOC. PERKIN TRANS., 1978, PART 1, NO 9, 1088-1090
  作者：CLARKE C.T.、 ELLIOTT J. D.、 JONES J. H.

  DOI：——

  日期：——