tert-butyl (2-cyano-1-(4-fluorophenyl)allyl) carbonate | 1381860-26-9

• 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: tert-butyl (2-cyano-1-(4-fluorophenyl)allyl) carbonate
• CAS: 1381860-26-9
• 化学式: C₁₅H₁₆FNO₃
• 分子量: 277.295
• InChiKey: AOZOJSWQZMYFBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.32
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2,4,6-环庚三烯-1-亚基)丙二腈 、 tert-butyl (2-cyano-1-(4-fluorophenyl)allyl) carbonate 在 三苯基膦 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以78%的产率得到2-((1S,6R,9S)-8-cyano-9-(4-fluorophenyl)bicyclo[4.3.1]deca-2,4,7-trien-10-ylidene)malononitrile
  参考文献：
  名称：

  [6 + 3] Morita-Baylis-Hillman 碳酸盐和二氰基七富烯的环化

  摘要：

  Morita-Baylis-Hillman 碳酸盐和二氰基七富烯的 [6 + 3] 环化反应是通过使用市售的三苯基膦作为路易斯碱催化剂来完成的。一系列密集功能化的双环[4.3.1]癸烷结构被有效地构建，具有独特的非对映选择性和良好的产率（高达 95%）。

  DOI：

  10.1039/d1ob00854d

文献信息

• DABCO- and DBU-promoted one-pot reaction of <i>N</i>-sulfonyl ketimines with Morita–Baylis–Hillman carbonates: a sequential approach to (2-hydroxyaryl)nicotinate derivatives
  作者：Soumitra Guin、Raman Gupta、Debashis Majee、Sampak Samanta

  DOI：10.3762/bjoc.14.254

  日期：——

  important class of (2-hydroxyaryl)pyridine derivatives bearing a carboxylate or a nitrile group suitably placed at C3 position of the aza-ring has been achieved in acceptable chemical yields with a broad functional group tolerance. This sequential C-C/C-N bond making process proceeds through a regioselective allylic alkylation/aza-Michael reaction between MBH carbonates derived from an acrylate/acrylonitrile

  令人陶醉的DABCO催化和DBU促进的一锅合成重要的一类重要的（2-羟基芳基）吡啶衍生物，带有适当地位于氮杂环C3位的羧酸盐或腈基，并具有可接受的化学收率。广泛的功能组耐受性。这种连续的CC / CN键形成过程是通过DABCO催化的丙烯酸酯/丙烯腈MBH碳酸酯与N-磺酰基酮亚胺之间的区域选择性烯丙基烷基化/氮杂-Michael反应进行的，然后由DABCO催化，然后消除SO2。碱的影响以及随后在露天气氛中的芳香化。
• Highly Enantioselective Regiodivergent Allylic Alkylations of MBH Carbonates with Phthalides
  作者：Fangrui Zhong、Jie Luo、Guo-Ying Chen、Xiaowei Dou、Yixin Lu

  DOI：10.1021/ja303115m

  日期：2012.6.20

  Phthalides were used for the first time in the allylic alkylation reactions with MBH carbonates for the creation of chiral 3,3-disubstituted phthalides. Highly enantioselective regiodivergent synthesis of gamma-selective or beta-selective allylic alkylation products was achieved by employing bifunctional chiral phosphines or multifunctional tertiary amine-thioureas as the catalyst, respectively. It was demonstrated that proper selection of catalysts and reaction conditions would differentiate an S(N)2'-S(N)2' pathway and an addition-elimination process, yielding different regioisomers of the allylic alkylation products in a highly enantiomerically pure form.