tert-butyl (2-cyano-5-phenylpent-1-en-3-yl) carbonate | 1381860-40-7

• 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-5-phenylpent-1-en-3-yl) carbonate
• CAS: 1381860-40-7
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: MKCRJIPVAFPNHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 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-5-phenylpent-1-en-3-yl) carbonate 在 三苯基膦 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以95%的产率得到2-((1S,6R,9R)-8-cyano-9-phenethylbicyclo[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

• Stereoselective synthesis of organosulfur compounds incorporating N-aromatic heterocyclic motifs and quaternary carbon centers via a sulfa-Michael triggered tandem reaction
  作者：Tianyou Qin、Lu Cheng、Sean Xiao-An Zhang、Weiwei Liao

  DOI：10.1039/c5cc01875g

  日期：——

  The novel sulfa-Michael addition (SMA)-triggered tandem reaction was developed by combining a SMA reaction with a simultaneous rearomatization process.

  这种新型的磺胺-迈克尔加成（SMA）触发串联反应是通过将SMA反应与同时的重芳构化过程结合而开发的。
• Lewis Base-Catalyzed One-Pot Cascade Sequences of <i>O</i>-Alkenyl-Substituted Cyanohydrins: Diastereoselective Synthesis of Multisubstituted Dihydrofurans
  作者：Shan-Tao Du、Zhen Sun、Wei Liu、Wei-Wei Liao

  DOI：10.1021/acs.orglett.7b03301

  日期：2017.12.15

  of the diastereoselective construction of polysubstituted 2,3-dihydrofurans incorporating contiguous quaternary and tertiary carbon centers via a Lewis base-catalyzed one-pot cascade sequence is described. The diversity and complexity of the final products can be efficiently constructed with high diastereoselectivities via this catalytic multistep process under mild reaction conditions.

  描述了通过路易斯碱催化的一锅级联序列并入连续的季碳和叔碳中心的多取代的2，3-二氢呋喃的非对映选择性构建的第一个例子。通过在温和的反应条件下进行催化多步法，可以高非对映选择性有效地构建最终产物的多样性和复杂性。
• 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.