(3RS,4SR)-3-t-butyldimethyl-silyloxy-4-phenyl-1-cyclopentanone | 114738-30-6

• 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: (3RS,4SR)-3-t-butyldimethyl-silyloxy-4-phenyl-1-cyclopentanone
• 英文别名: (3R^*,4S^*)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylcyclopentan-1-one；(3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-4-phenylcyclopentan-1-one
• CAS: 114738-30-6
• 化学式: C₁₇H₂₆O₂Si
• 分子量: 290.478
• InChiKey: RAKAHFKRAVJQBC-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3RS,4SR)-3-t-butyldimethyl-silyloxy-4-phenyl-1-cyclopentanone 在 sodium tetrahydroborate 、 四溴化碳 、 四丁基氟化铵 、 双氧水 、 silver trifluoroacetate 、 L-Selectride 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 18.58h， 生成 1-hydroxy-3-phenylcyclopent-2-ene
  参考文献：
  名称：

  Formation of 1-phenyl-2,3-dioxabicyclo[2.2.1]heptane in the reaction of 1,3-dibromo-4-phenylcyclopentane with hydrogen peroxide in the presence of silver trifluoroacetate

  摘要：

  DOI：

  10.1021/jo00248a035
• 作为产物：
  描述：

  4-((tert-butyldimethylsilyl)oxy)-3-penten-2-one 在 copper(l) iodide 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 (3RS,4SR)-3-t-butyldimethyl-silyloxy-4-phenyl-1-cyclopentanone
  参考文献：
  名称：

  Formation of 1-phenyl-2,3-dioxabicyclo[2.2.1]heptane in the reaction of 1,3-dibromo-4-phenylcyclopentane with hydrogen peroxide in the presence of silver trifluoroacetate

  摘要：

  DOI：

  10.1021/jo00248a035

文献信息

• Synthesis of a prostaglandin endoperoxide model compound and its reaction with electron transfer reagents
  作者：Kimio Takahashi、Morio Kishi

  DOI：10.1016/s0040-4020(01)86176-7

  日期：1988.1

  5-Exo-phenyl-2,3-dioxabicyclo[2.2.1]heptane (4c) was synthesized as a model compound of prostaglandin endoperoxide (PGH) to mimic the bioconversion of PGH into thromboxane (TX). The reaction of (4c) with various electron transfer reagents was investigated. With the aid of a catalytic amount of ferrous ion, (4c) was successfully converted into the thromboxane B (TXB) skeleton.

  合成了5-Exo-phenyl-2,3-dioxabicyclocyclo [2.2.1]庚烷（4c）作为内生前列腺素（PGH）的模型化合物，以模拟PGH到血栓烷（TX）的生物转化。研究了（4c）与各种电子转移试剂的反应。借助催化量的亚铁离子，成功地将（4c）转化为血栓烷B（TXB）骨架。
• <i>pseudo</i>Enantiomeric Carbohydrate Olefin Ligands - Case Study and Application in Kinetic Resolution in Rhodium(I)-Catalysed 1,4-Addition
  作者：Holger Grugel、Fabian Albrecht、Mike M. K. Boysen

  DOI：10.1002/adsc.201400459

  日期：2014.11.3

  AbstractIn order to investigate significant differences in asymmetric induction for pseudo enantiomeric carbohydrate olefin ligands in rhodium(I)‐catalysed 1,4‐addition reactions, we designed a set of new olefin ligands differing in relative configuration and pyranoside conformation. With these, we have successfully elucidated structural requirements for metal binding and also identified an improved alternative for one pseudo enantiomer. Furthermore, we report the efficient kinetic resolution of a racemic 4‐hydroxycyclopentenone derivative by 1,4‐addition.magnified image
• TAKAHASHI, KIMIO;KISHI, MORIO, TETRAHEDRON, 44,(1988) N 15, C. 4737-4746
  作者：TAKAHASHI, KIMIO、KISHI, MORIO

  DOI：——

  日期：——