(2S,3S)-(-)-methyl 2-(2-propenyl)-3-(tert-butoxycarbonylamino)pent-4-enonate | 1272666-19-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S)-(-)-methyl 2-(2-propenyl)-3-(tert-butoxycarbonylamino)pent-4-enonate
• 英文别名: methyl (2S,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-prop-2-enylpent-4-enoate
• CAS: 1272666-19-9
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: JVPYAGHAORJHDK-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-(-)-methyl 2-(2-propenyl)-3-(tert-butoxycarbonylamino)pent-4-enonate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 10% palladium on activated charcoal 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-(tert-butyloxycarbonyl)-trans-(1S,2S)-2-aminocyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of anti-α-Substituted β-Amino Ketones from Sulfinimines

  摘要：

  Previously unknown, enantiopure, beta-amino ketones were prepared in modest yield by addition of lithium reagents to N-sulfinyl anti-alpha-substituted beta-amino Weinreb amides. Grignard reagents failed to add to these Weinreb amides in contrast to the syn-alpha-substituted isomers which did. The anti-alpha-substituted beta-amino Weinreb amides were prepared by addition of LiN(OMe)Me to the corresponding N-sulfinyl anti-alpha-substituted beta-amino esters because alpha-alkylation of N-sulfinyl beta-amino Weinreb amide enolates resulted in poor diastereoselectivities.

  DOI：

  10.1021/jo2002352
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 以0.048 g的产率得到(2S,3S)-(-)-methyl 2-(2-propenyl)-3-(tert-butoxycarbonylamino)pent-4-enonate
  参考文献：
  名称：

  Asymmetric Synthesis of anti-α-Substituted β-Amino Ketones from Sulfinimines

  摘要：

  Previously unknown, enantiopure, beta-amino ketones were prepared in modest yield by addition of lithium reagents to N-sulfinyl anti-alpha-substituted beta-amino Weinreb amides. Grignard reagents failed to add to these Weinreb amides in contrast to the syn-alpha-substituted isomers which did. The anti-alpha-substituted beta-amino Weinreb amides were prepared by addition of LiN(OMe)Me to the corresponding N-sulfinyl anti-alpha-substituted beta-amino esters because alpha-alkylation of N-sulfinyl beta-amino Weinreb amide enolates resulted in poor diastereoselectivities.

  DOI：

  10.1021/jo2002352

文献信息

• Studies of a soluble polyethylene glycol immobilized ruthenium catalyst in aqueous media
  作者：Shazia Zaman、Hongyuan Chen、Andrew D. Abell

  DOI：10.1016/j.tetlet.2010.12.046

  日期：2011.2

  We have developed an air-stable soluble polyethylene glycol bound ruthenium catalyst which performs efficient ring-closing metathesis in organic solvents as well as in aqueous media.

  我们已经开发出了一种空气稳定的可溶性聚乙二醇键合钌催化剂，该催化剂在有机溶剂以及水性介质中都能进行有效的闭环复分解反应。
• Asymmetric Synthesis of <i>anti</i>-α-Substituted β-Amino Ketones from Sulfinimines
  作者：Franklin A. Davis、Peng Xu

  DOI：10.1021/jo2002352

  日期：2011.5.6

  Previously unknown, enantiopure, beta-amino ketones were prepared in modest yield by addition of lithium reagents to N-sulfinyl anti-alpha-substituted beta-amino Weinreb amides. Grignard reagents failed to add to these Weinreb amides in contrast to the syn-alpha-substituted isomers which did. The anti-alpha-substituted beta-amino Weinreb amides were prepared by addition of LiN(OMe)Me to the corresponding N-sulfinyl anti-alpha-substituted beta-amino esters because alpha-alkylation of N-sulfinyl beta-amino Weinreb amide enolates resulted in poor diastereoselectivities.