(4S)-4-(3-tert-butyldimethylsilyloxypropyl)-2-cyclopenten-1-one | 138622-67-0

• 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: (4S)-4-(3-tert-butyldimethylsilyloxypropyl)-2-cyclopenten-1-one
• 英文别名: (4R)-4-[3-[tert-butyl(dimethyl)silyl]oxypropyl]cyclopent-2-en-1-one
• CAS: 138622-67-0
• 化学式: C₁₄H₂₆O₂Si
• 分子量: 254.445
• InChiKey: YBFXEYOJMPLIQP-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  (4S)-4-(3-tert-butyldimethylsilyloxypropyl)-2-cyclopenten-1-one 在 水 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 (3S,4S)-3,4-bis(3-hydroxypropyl)cyclopentanone
  参考文献：
  名称：

  Synthesis of a new ketone and alcohol with C2 symmetry; (S,S,S,S) tricyclo[6.3.0.03,7]undecan-2-onela and (S,S,S,S) tricyclo[6.3.0.03,7]undecan-2-ollb

  摘要：

  Dissolving metal reduction of known enone 5 affords predominantly the racemic form of title ketone (3) whereas catalytic reduction gives the meso isomer 6. Neither ketone 3 nor alcohol 4 could be satisfactorily resolved. Asymmetric synthesis of (-)-3 and (+)-4 (ee = 91%) was effected from ketone (+)-13.

  DOI：

  10.1016/s0957-4166(00)86156-x
• 作为产物：
  描述：

  (3-溴丙氧基)叔丁基二甲基硅烷 以 邻二氯苯 为溶剂， 反应 5.0h， 生成 (4S)-4-(3-tert-butyldimethylsilyloxypropyl)-2-cyclopenten-1-one
  参考文献：
  名称：

  Synthesis of a new ketone and alcohol with C2 symmetry; (S,S,S,S) tricyclo[6.3.0.03,7]undecan-2-onela and (S,S,S,S) tricyclo[6.3.0.03,7]undecan-2-ollb

  摘要：

  Dissolving metal reduction of known enone 5 affords predominantly the racemic form of title ketone (3) whereas catalytic reduction gives the meso isomer 6. Neither ketone 3 nor alcohol 4 could be satisfactorily resolved. Asymmetric synthesis of (-)-3 and (+)-4 (ee = 91%) was effected from ketone (+)-13.

  DOI：

  10.1016/s0957-4166(00)86156-x

文献信息

• Synthesis of a new ketone and alcohol with C2 symmetry; (S,S,S,S) tricyclo[6.3.0.03,7]undecan-2-onela and (S,S,S,S) tricyclo[6.3.0.03,7]undecan-2-ollb
  作者：John M. McIntosh、Kenneth C. Cassidy

  DOI：10.1016/s0957-4166(00)86156-x

  日期：1991.1

  Dissolving metal reduction of known enone 5 affords predominantly the racemic form of title ketone (3) whereas catalytic reduction gives the meso isomer 6. Neither ketone 3 nor alcohol 4 could be satisfactorily resolved. Asymmetric synthesis of (-)-3 and (+)-4 (ee = 91%) was effected from ketone (+)-13.