4-Hydroxy-2-((E)-3-hydroxy-1-methyl-propenyl)-5-methyl-benzoic acid methyl ester | 114092-41-0

• 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: 4-Hydroxy-2-((E)-3-hydroxy-1-methyl-propenyl)-5-methyl-benzoic acid methyl ester
• 英文别名: methyl 4-hydroxy-2-[(E)-4-hydroxybut-2-en-2-yl]-5-methylbenzoate
• CAS: 114092-41-0
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: JCTWCHNKVDWMEG-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-4-Methyl-6-trimethylsilanyloxy-hex-4-en-2-ynoic acid methyl ester 、 (E)-3-methyl-4-methoxy-2-[(trimethylsilyl)oxy]-1,3-butadiene 以8%的产率得到
  参考文献：
  名称：

  KOCIENSKI, PHILIP J.;STREET, STEPHEN D. A.;YEATES, CLIVE;CAMPBELL, SIMON +, J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 10, 2171-2181

  摘要：

  DOI：

文献信息

• Highly Selective Diels-Alder Reactions of Directly Connected Enyne Dienophiles
  作者：Mingji Dai、David Sarlah、Maolin Yu、Samuel J. Danishefsky、Gavin O. Jones、K. N. Houk

  DOI：10.1021/ja065762u

  日期：2007.1.1

  The paper describes the course of cycloadditions of Diels-Alder dienophiles containing linked enyne sites, each substituted with activating groups. Consistently, it was found that in the enyne cases the Diels-Alder reaction occurred specifically at the acetylenic center. Furthermore, it was found that the regiochemical sense of the cycloaddition was apparently determined by the remote activating group bound to the olefinic site. This remote acrylyl group totally dominated the course of the cycloaddition, relative to the activating group bound directly on the acetylene site. Explanations for these findings at the computational level are provided. The computations also rationalize the strong preference for cycloaddition to occur at the acetylene linkage and encompass the otherwise surprising regiochemical dominance by the remote ester on the olefinic site. The high selectivities available through such reactions provide important new opportunities in the synthesis of orsenillate type substructures that are found in a variety of natural products of contemporary interest.
• Kocienski, Philip J.; Street, Stephen D. A.; Yeates, Clive, Journal of the Chemical Society. Perkin transactions I, 1987, p. 2171 - 2182
  作者：Kocienski, Philip J.、Street, Stephen D. A.、Yeates, Clive、Campbell, Simon F.

  DOI：——

  日期：——
• KOCIENSKI, PHILIP J.;STREET, STEPHEN D. A.;YEATES, CLIVE;CAMPBELL, SIMON +, J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 10, 2171-2181
  作者：KOCIENSKI, PHILIP J.、STREET, STEPHEN D. A.、YEATES, CLIVE、CAMPBELL, SIMON +

  DOI：——

  日期：——