tert-butyl N-[(1S,4R)-4-[tert-butyl(diphenyl)silyl]oxycyclopent-2-en-1-yl]carbamate | 817210-67-6

• 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: tert-butyl N-[(1S,4R)-4-[tert-butyl(diphenyl)silyl]oxycyclopent-2-en-1-yl]carbamate
• CAS: 817210-67-6
• 化学式: C₂₆H₃₅NO₃Si
• 分子量: 437.654
• InChiKey: WMKNHXDGKKPIKR-RTWAWAEBSA-N

物化性质

• 沸点：
  499.9±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S,4R)-4-[tert-butyl(diphenyl)silyl]oxycyclopent-2-en-1-yl]carbamate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以64%的产率得到[(1S,4R)-4-羟基-2-环戊烯-1-基](2-甲基-2-丙基)氨基甲酸
  参考文献：
  名称：

  Chiral base route to functionalised cyclopentenyl amines: formal synthesis of the cyclopentene core of nucleoside Q

  摘要：

  A chiral base route to a range of highly functionalised amino cyclopentenes has been developed. The key asymmetric step involved the chiral lithium amide base-mediated rearrangement of a protected trans-4-hydroxy cyclopentene oxide to give an allylic alcohol (88% ee). Subsequent Overman rearrangement gave a protected trans-1,2-aminocyclopentenol whereas Mitsunobu substitution with BocNHNs gave a protected cis-amino cyclopentenol. Both are proven intermediates for natural product synthesis. The protected cis-aminocyclopentenol was transformed in a few steps into a precursor of the cyclopentene core of nucleoside Q, a natural product whose deficiency in animals is related to tumour growth. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.043
• 作为产物：
  描述：

  N-(叔丁氧羰基)-2-硝基苯酰胺 在 lithium hydroxide 、 偶氮二甲酸二异丙酯 、 巯基乙酸 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 90.0h， 生成 tert-butyl N-[(1S,4R)-4-[tert-butyl(diphenyl)silyl]oxycyclopent-2-en-1-yl]carbamate
  参考文献：
  名称：

  Chiral base route to functionalised cyclopentenyl amines: formal synthesis of the cyclopentene core of nucleoside Q

  摘要：

  A chiral base route to a range of highly functionalised amino cyclopentenes has been developed. The key asymmetric step involved the chiral lithium amide base-mediated rearrangement of a protected trans-4-hydroxy cyclopentene oxide to give an allylic alcohol (88% ee). Subsequent Overman rearrangement gave a protected trans-1,2-aminocyclopentenol whereas Mitsunobu substitution with BocNHNs gave a protected cis-amino cyclopentenol. Both are proven intermediates for natural product synthesis. The protected cis-aminocyclopentenol was transformed in a few steps into a precursor of the cyclopentene core of nucleoside Q, a natural product whose deficiency in animals is related to tumour growth. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.043

文献信息

• Chiral base route to functionalised cyclopentenyl amines: formal synthesis of the cyclopentene core of nucleoside Q
  作者：Sally J. Oxenford、Peter O’Brien、Mark R. Shipton

  DOI：10.1016/j.tetlet.2004.10.043

  日期：2004.11

  A chiral base route to a range of highly functionalised amino cyclopentenes has been developed. The key asymmetric step involved the chiral lithium amide base-mediated rearrangement of a protected trans-4-hydroxy cyclopentene oxide to give an allylic alcohol (88% ee). Subsequent Overman rearrangement gave a protected trans-1,2-aminocyclopentenol whereas Mitsunobu substitution with BocNHNs gave a protected cis-amino cyclopentenol. Both are proven intermediates for natural product synthesis. The protected cis-aminocyclopentenol was transformed in a few steps into a precursor of the cyclopentene core of nucleoside Q, a natural product whose deficiency in animals is related to tumour growth. (C) 2004 Elsevier Ltd. All rights reserved.