(R)-2-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylpropanamide | 225928-45-0

• 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: (R)-2-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylpropanamide
• 英文别名: (2R)-2-[tert-butyl(dimethyl)silyl]oxy-N-methoxy-N-methylpropanamide
• CAS: 225928-45-0
• 化学式: C₁₁H₂₅NO₃Si
• 分子量: 247.41
• InChiKey: FUJDWNVNKXFHLM-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (R)-2-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylpropanamide 在 正丁基锂 、 氯 、 柠檬酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 4.5h， 生成 3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-chloro-cyclopent-2-enone
  参考文献：
  名称：

  An efficient synthesis of 2-cyclopentenones from γ-ketoaldehyde acetals using lithium trimethylsilyldiazomethane. Its application to the synthesis of trichodenone C

  摘要：

  The reaction of gamma-ketoaldehyde acetals with lithium trimethylsilyldiazomethane afforded 2-cyclopentenones via the 1,5-C-H insertion of alkylidene carbene in high to moderate yields. Using this method, the synthesis of trichodenone C was achieved. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01162-x
• 作为产物：
  描述：

  (R)-2-((叔丁基二甲基甲硅烷基)氧基)丙酸甲酯 在 lithium hydroxide 、 氰基磷酸二乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-2-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylpropanamide
  参考文献：
  名称：

  An efficient synthesis of 2-cyclopentenones from γ-ketoaldehyde acetals using lithium trimethylsilyldiazomethane. Its application to the synthesis of trichodenone C

  摘要：

  The reaction of gamma-ketoaldehyde acetals with lithium trimethylsilyldiazomethane afforded 2-cyclopentenones via the 1,5-C-H insertion of alkylidene carbene in high to moderate yields. Using this method, the synthesis of trichodenone C was achieved. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01162-x

文献信息

• Bioinspired Total Synthesis and Stereochemical Revision of the Fungal Metabolite Pestalospirane B
  作者：Sandhya Badrinarayanan、Christopher J. Squire、Jonathan Sperry、Margaret A. Brimble

  DOI：10.1021/acs.orglett.7b01371

  日期：2017.7.7

  The total synthesis of both enantiomers of pestalospirane B, 2, has been achieved using a bioinspired tandem dimerization–spiroketalization reaction. Electronic circular dichroism (ECD) and X-ray analysis were used to revise the absolute stereochemistry of the natural product pestalospirane B from 3S, 3′S, 12R, 12′R to its enantiomer 3R, 3′R, 12S, 12′S.

  使用生物启发的串联二聚化-螺缩酮化反应已实现了香豆螺烷B，2的两个对映异构体的总合成。电子圆二色性（ECD）和X射线分析被用来从3修改天然产物pestalospirane B的绝对立体化学小号，3'小号，12 - [R，12' - [R到其对映体3 - [R，3' - [R，12小号，12 'S。
• Syntheses of (−)-Tatarinoid A, (±)-Tatarinoid B, and (−)-Tatarinoid C
  作者：Yuriy Slutskyy、William T. Jewell、Claudia G. Lucero

  DOI：10.1016/j.tetlet.2012.10.104

  日期：2013.1

  The syntheses of (-)-Tatarinoid A, (+/-)-Tatarinoid B, and (-)-Tatarinoid C in one to three steps are described herein. (-)-Tatarinoid A and (-)-Tatarinoid C are both constructed in three steps from 1-bromo-2,4,5-trimethoxybenzene in overall yields of 63% and 74%, respectively. The addition of (1-methoxyethyl)triphenylphosphonium ylide to 2,4,5-trimethoxybenzaldehyde provides (+/-)-Tatarinoid B in one step in 97% yield. Published by Elsevier Ltd.
• The efficient stereoselective synthesis of (2S,3R,4S,5S,6S,11E)-3-amino-6-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic acid (AMMTD), a component of microsclerodermins of marine sponge origin, as its protected form
  作者：Shigekazu Sasaki、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/s0040-4039(99)00411-6

  日期：1999.4

  The title acid, a component of microsclerodermins of marine sponge origin having five consecutive stereogenic centers, was efficiently synthesized as its protected form 1 from the alcohol 5 utilizing the stereoselective addition of anisole to the acetylenic triple bond and the anti-aldol reaction as key steps. (C) 1999 Elsevier Science Ltd. All rights reserved.
• An efficient synthesis of 2-cyclopentenones from γ-ketoaldehyde acetals using lithium trimethylsilyldiazomethane. Its application to the synthesis of trichodenone C
  作者：Atsushi Sakai、Toyohiko Aoyama、Takayuki Shioiri

  DOI：10.1016/s0040-4039(00)01162-x

  日期：2000.8

  The reaction of gamma-ketoaldehyde acetals with lithium trimethylsilyldiazomethane afforded 2-cyclopentenones via the 1,5-C-H insertion of alkylidene carbene in high to moderate yields. Using this method, the synthesis of trichodenone C was achieved. (C) 2000 Elsevier Science Ltd. All rights reserved.