1-[1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methanamine | 737790-49-7

• 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: 1-[1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methanamine
• 英文别名: [1-[[Tert-butyl(dimethyl)silyl]oxymethyl]cyclopropyl]methanamine
• CAS: 737790-49-7
• 化学式: C₁₁H₂₅NOSi
• 分子量: 215.411
• InChiKey: BETIZJQWWDLROF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methanamine 在 N-Boc-L-缬氨酸 、 sodium 2,2,2-trifluoroacetate 、 palladium diacetate 、 三乙胺 、 silver carbonate 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 18.08h， 生成 N-((1-(((tert-butyldimethylsilyl)oxy)methyl)-2-(p-tolyl)cyclopropyl)methyl)-1,1,1-trifluoromethanesulfonamide
  参考文献：
  名称：

  Palladium(II)-Catalyzed Highly Enantioselective C–H Arylation of Cyclopropylmethylamines

  摘要：

  C-H arylation via a Pd(II)/Pd(IV) catalytic cycle has been one of the most extensively studied C-H activation reactions since the 1990s. Despite the rapid development of this reaction in the past two decades, an enantioselective version has not been reported to date. Herein, we report a Pd(II)-catalyzed highly enantioselective (up to 99.5% ee) arylation of cyclopropyl C-H bonds with aryl iodides using mono-N-protected amino acid (MPAA) ligands, providing a new route for the preparation of chiral cis-aryl-cyclopropylmethylamines. The enantiocontrol is also shown to override the diastereoselectivity of chiral substrates.

  DOI：

  10.1021/ja512529e
• 作为产物：
  描述：

  1-(aminocarbonyl)-1-cyclopropanecarboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-[1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methanamine
  参考文献：
  名称：

  Palladium(II)-Catalyzed Highly Enantioselective C–H Arylation of Cyclopropylmethylamines

  摘要：

  C-H arylation via a Pd(II)/Pd(IV) catalytic cycle has been one of the most extensively studied C-H activation reactions since the 1990s. Despite the rapid development of this reaction in the past two decades, an enantioselective version has not been reported to date. Herein, we report a Pd(II)-catalyzed highly enantioselective (up to 99.5% ee) arylation of cyclopropyl C-H bonds with aryl iodides using mono-N-protected amino acid (MPAA) ligands, providing a new route for the preparation of chiral cis-aryl-cyclopropylmethylamines. The enantiocontrol is also shown to override the diastereoselectivity of chiral substrates.

  DOI：

  10.1021/ja512529e

文献信息

• Thienopyrimidine compounds and use thereof
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1591446B1

  公开（公告）日：2013-03-06
• Palladium(II)-Catalyzed Highly Enantioselective C–H Arylation of Cyclopropylmethylamines
  作者：Kelvin S. L. Chan、Hai-Yan Fu、Jin-Quan Yu

  DOI：10.1021/ja512529e

  日期：2015.2.11

  C-H arylation via a Pd(II)/Pd(IV) catalytic cycle has been one of the most extensively studied C-H activation reactions since the 1990s. Despite the rapid development of this reaction in the past two decades, an enantioselective version has not been reported to date. Herein, we report a Pd(II)-catalyzed highly enantioselective (up to 99.5% ee) arylation of cyclopropyl C-H bonds with aryl iodides using mono-N-protected amino acid (MPAA) ligands, providing a new route for the preparation of chiral cis-aryl-cyclopropylmethylamines. The enantiocontrol is also shown to override the diastereoselectivity of chiral substrates.