(3S,4S)-3-allyl-2-methyl-4-methoxy-1-(trimethylsilyloxy)cyclopent-1-ene | 1450728-29-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3S,4S)-3-allyl-2-methyl-4-methoxy-1-(trimethylsilyloxy)cyclopent-1-ene
• 英文别名: [(3S,4S)-4-methoxy-2-methyl-3-prop-2-enylcyclopenten-1-yl]oxy-trimethylsilane
• CAS: 1450728-29-6
• 化学式: C₁₃H₂₄O₂Si
• 分子量: 240.418
• InChiKey: RPZZJUQLPPDXMX-AAEUAGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-4-hydroxy-2-methylcyclopent-2-en-1-one 在 五氯化钽 、 silver(l) oxide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (3S,4S)-3-allyl-2-methyl-4-methoxy-1-(trimethylsilyloxy)cyclopent-1-ene
  参考文献：
  名称：

  An Enantioselective Total Synthetic Approach to (+)-Heptemerone G and (+)-Guanacastepene A from 2-Furyl Methyl Carbinol

  摘要：

  An enantioselective synthesis of the key bicyclic building block for (+)-heptemerone G and (+)-guanacastepene A construction has been accomplished. 2-Furyl methyl carbinol was used as the starting material and (S)-4-hydroxy-2-methylcyclopent-2-en-1-one as the primal optically active intermediate.

  DOI：

  10.1055/s-0033-1338857

文献信息

• A convenient preparation of (S)-(−)-4-hydroxy-2-methylcyclopent-2-en-1-one and its application as a chiral synthetic equivalent of 2-methylcyclopent-2-en-1-one in the terpenoid synthesis
  作者：Karol Michalak、Jerzy Wicha

  DOI：10.1016/j.tet.2014.06.006

  日期：2014.8

  from 1-(2-furyl)ethanol using modified Piancatelli rearrangement and enzymatic kinetic resolution of the racemate was developed. An application of O-protected derivatives of 4-hydroxy-2-methylcyclopent-2-en-1-one to terpenoid synthesis through tandem conjugate addition of allyl-metal reagents, enolate trapping, and consecutive Mukaiyama–Michael addition was studied. An optically active azulene derivative

  开发了一种通过修饰的Piancatelli重排和消旋体的酶促动力学拆分从1-（2-呋喃基）乙醇制备（S）-4-羟基-2-甲基环戊-2-烯-1-酮的方法。通过串联共轭添加烯丙基金属试剂，烯醇盐捕集和连续Mukaiyama-Michael加成反应，研究了O-保护的4-羟基-2-甲基环戊-2-烯-1-酮在萜类化合物合成中的应用。有效地合成了可用于类萜合成的旋光性z青烯衍生物。