2-(R)-amino-1-(tert-butylmethylphenylsilyloxy)butane | 224949-97-7

• 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: 2-(R)-amino-1-(tert-butylmethylphenylsilyloxy)butane
• 英文别名: (2R)-1-(tert-butyl-methyl-phenylsilyl)oxybutan-2-amine
• CAS: 224949-97-7
• 化学式: C₁₅H₂₇NOSi
• 分子量: 265.471
• InChiKey: ZGDKMWBWOUBXIO-YJJYDOSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  2-(R)-amino-1-(tert-butylmethylphenylsilyloxy)butane 生成 2-(R)-amino-1-(tert-butylmethylphenyl-Si(R)-silyloxy)butane hydrochloride
  参考文献：
  名称：

  Facile synthesis of enantiomerically pure tert-butyl(methyl)phenylsilanes

  摘要：

  A method for the preparation of both enantiomers of tert-butyl(methyl)phenylsilane 2 is presented. Racemic tert-butyl(methyl)phenylsilyl chloride 3 was allowed to react with (R)-(-)-2-amino-1-butanol 4 to give hydrochloride 5. Diastereomer separation via treatment of the respective free amine 6 with 0.5 mol equivalent of HCl in hexane-2-propanol yielded crystalline diastereomerically pure hydrochloride (R)Si-5. The corresponding free amine (R)Si-6 was reduced with LiAlH4 to give (S)-2. The mother liquors obtained after separation of (R)Si-5 on treatment with oxalic acid provided a crystalline salt that eventually afforded (R)-2. The optical purity of (S)-2 (98% ee) was documented by its reaction (hydrosilylation) with propargylic alcohol derivative 10 and HPLC analysis of product lr using a chiral column. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00022-1
• 作为产物：
  描述：

  甲基苯基二氯硅烷 在 ammonium hydroxide 作用下， 以 正戊烷 为溶剂， 反应 50.0h， 生成 2-(R)-amino-1-(tert-butylmethylphenylsilyloxy)butane
  参考文献：
  名称：

  Facile synthesis of enantiomerically pure tert-butyl(methyl)phenylsilanes

  摘要：

  A method for the preparation of both enantiomers of tert-butyl(methyl)phenylsilane 2 is presented. Racemic tert-butyl(methyl)phenylsilyl chloride 3 was allowed to react with (R)-(-)-2-amino-1-butanol 4 to give hydrochloride 5. Diastereomer separation via treatment of the respective free amine 6 with 0.5 mol equivalent of HCl in hexane-2-propanol yielded crystalline diastereomerically pure hydrochloride (R)Si-5. The corresponding free amine (R)Si-6 was reduced with LiAlH4 to give (S)-2. The mother liquors obtained after separation of (R)Si-5 on treatment with oxalic acid provided a crystalline salt that eventually afforded (R)-2. The optical purity of (S)-2 (98% ee) was documented by its reaction (hydrosilylation) with propargylic alcohol derivative 10 and HPLC analysis of product lr using a chiral column. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00022-1

文献信息

• Facile synthesis of enantiomerically pure tert-butyl(methyl)phenylsilanes
  作者：Paweł Jankowski、Ernst Schaumann、Jerzy Wicha、Andrzej Zarecki、Gunadi Adiwidjaja

  DOI：10.1016/s0957-4166(99)00022-1

  日期：1999.2

  A method for the preparation of both enantiomers of tert-butyl(methyl)phenylsilane 2 is presented. Racemic tert-butyl(methyl)phenylsilyl chloride 3 was allowed to react with (R)-(-)-2-amino-1-butanol 4 to give hydrochloride 5. Diastereomer separation via treatment of the respective free amine 6 with 0.5 mol equivalent of HCl in hexane-2-propanol yielded crystalline diastereomerically pure hydrochloride (R)Si-5. The corresponding free amine (R)Si-6 was reduced with LiAlH4 to give (S)-2. The mother liquors obtained after separation of (R)Si-5 on treatment with oxalic acid provided a crystalline salt that eventually afforded (R)-2. The optical purity of (S)-2 (98% ee) was documented by its reaction (hydrosilylation) with propargylic alcohol derivative 10 and HPLC analysis of product lr using a chiral column. (C) 1999 Elsevier Science Ltd. All rights reserved.