(2R,3S)-2,3-isopropylidenedioxy-4-phenylthio-4-cyclopenten-1-one | 1023699-75-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2R,3S)-2,3-isopropylidenedioxy-4-phenylthio-4-cyclopenten-1-one
• CAS: 1023699-75-3
• 化学式: C₁₄H₁₄O₃S
• 分子量: 262.329
• InChiKey: HRQWIHQSHFIDSV-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2,3-isopropylidenedioxy-4-phenylthio-4-cyclopenten-1-one 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以99%的产率得到(1S,2S,3S)-2,3-isopropylidenedioxy-4-phenylthio-4-cyclopenten-1-ol
  参考文献：
  名称：

  Radical-mediated stannylation of vinyl sulfones: access to novel 4′-modified neplanocin A analogues

  摘要：

  Synthesis of 4'-substituted (halogeno, phenyl, ethynyl, and cyano) neplanocin A analogues was carried out. A cyclopentenol derivative having a vinylstannane structure was designed as key-intermediate in this study, which was prepared based on radical-mediated sulfur-extrusive stannylation. The resulting stannylated cyclopentenol 15 was successfully condensed with 6-chloropurine through the Mitsunobu reaction, leading to the carbocyclic nucleoside 20. Compound 20 was converted to its adenine counterpart 21 by treatment with NH(3)/MeOH, during which the 4'-stannyl group remained intact. The title compounds were prepared by using 21 or the 4'-iodo derivative (22) mostly through the Stille reaction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.039
• 作为产物：
  描述：

  (2R,3S)-2,3-isopropylidenedioxy-4-(phenylthio)cyclopentan-1-one 在 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以94%的产率得到(2R,3S)-2,3-isopropylidenedioxy-4-phenylthio-4-cyclopenten-1-one
  参考文献：
  名称：

  Radical-mediated stannylation of vinyl sulfones: access to novel 4′-modified neplanocin A analogues

  摘要：

  Synthesis of 4'-substituted (halogeno, phenyl, ethynyl, and cyano) neplanocin A analogues was carried out. A cyclopentenol derivative having a vinylstannane structure was designed as key-intermediate in this study, which was prepared based on radical-mediated sulfur-extrusive stannylation. The resulting stannylated cyclopentenol 15 was successfully condensed with 6-chloropurine through the Mitsunobu reaction, leading to the carbocyclic nucleoside 20. Compound 20 was converted to its adenine counterpart 21 by treatment with NH(3)/MeOH, during which the 4'-stannyl group remained intact. The title compounds were prepared by using 21 or the 4'-iodo derivative (22) mostly through the Stille reaction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.039