benzyl (3R)-3-[(t-butyldiphenylsilyl)oxy]-3,6-dihydropyridine-1(2H)-carboxylate | 804500-77-4

• 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: benzyl (3R)-3-[(t-butyldiphenylsilyl)oxy]-3,6-dihydropyridine-1(2H)-carboxylate
• 英文别名: benzyl (3R)-3-[tert-butyl(diphenyl)silyl]oxy-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 804500-77-4
• 化学式: C₂₉H₃₃NO₃Si
• 分子量: 471.671
• InChiKey: QZFLFRKDKNXNTR-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl (3R)-3-[(t-butyldiphenylsilyl)oxy]-3,6-dihydropyridine-1(2H)-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以99%的产率得到benzyl (3R)-3-hydroxy-3,6-dihydropyridine-1(2H)-carboxylate
  参考文献：
  名称：

  Conversion of chiral unsaturated cyanohydrins into chiral carba- and heterocycles via ring-closing metathesis

  摘要：

  Aliphatic unsaturated cyanohydrins 1-3 served as starting materials in the synthesis of a set of new chiral unsaturated cyclic 1,2-ethanolamines. Combining a Grignard addition-NaBH4 reduction sequence with a ring-closing metathesis afforded unsaturated cyclic 1,2-ethanolamines 7-11 and 22-25 in good yields and high ee (96-99%). The conversion of cyanohydrins 1-3 via a DIBAL reduction-transimination-NaBH4 reduction sequence, using allylamine, followed by ring-closing metathesis yielded tetrahydropyridines 28, tetrahydroazepinols 33 and tetrahydroazocinols 34 in high yields and excellent ee (97-99%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.103
• 作为产物：
  描述：

  (5R,6E)-5-(t-butyldiphenylsilyl)oxyocta-1,6-diene-4-amine 在 Grubbs catalyst first generation 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 benzyl (3R)-3-[(t-butyldiphenylsilyl)oxy]-3,6-dihydropyridine-1(2H)-carboxylate
  参考文献：
  名称：

  Conversion of chiral unsaturated cyanohydrins into chiral carba- and heterocycles via ring-closing metathesis

  摘要：

  Aliphatic unsaturated cyanohydrins 1-3 served as starting materials in the synthesis of a set of new chiral unsaturated cyclic 1,2-ethanolamines. Combining a Grignard addition-NaBH4 reduction sequence with a ring-closing metathesis afforded unsaturated cyclic 1,2-ethanolamines 7-11 and 22-25 in good yields and high ee (96-99%). The conversion of cyanohydrins 1-3 via a DIBAL reduction-transimination-NaBH4 reduction sequence, using allylamine, followed by ring-closing metathesis yielded tetrahydropyridines 28, tetrahydroazepinols 33 and tetrahydroazocinols 34 in high yields and excellent ee (97-99%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.103

文献信息

• Conversion of chiral unsaturated cyanohydrins into chiral carba- and heterocycles via ring-closing metathesis
  作者：Adrianus M.C.H. van den Nieuwendijk、Amar B.T. Ghisaidoobe、Herman S. Overkleeft、Johannes Brussee、Arne van der Gen

  DOI：10.1016/j.tet.2004.07.103

  日期：2004.11

  Aliphatic unsaturated cyanohydrins 1-3 served as starting materials in the synthesis of a set of new chiral unsaturated cyclic 1,2-ethanolamines. Combining a Grignard addition-NaBH4 reduction sequence with a ring-closing metathesis afforded unsaturated cyclic 1,2-ethanolamines 7-11 and 22-25 in good yields and high ee (96-99%). The conversion of cyanohydrins 1-3 via a DIBAL reduction-transimination-NaBH4 reduction sequence, using allylamine, followed by ring-closing metathesis yielded tetrahydropyridines 28, tetrahydroazepinols 33 and tetrahydroazocinols 34 in high yields and excellent ee (97-99%). (C) 2004 Elsevier Ltd. All rights reserved.