(Z)-(S)-N-Boc-2-amino-3-nonenol | 133626-01-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-(S)-N-Boc-2-amino-3-nonenol
• 英文别名: (S,Z)-tert-butyl-1-hydroxynon-3-en-2-ylcarbamate；tert-butyl N-[(Z,2S)-1-hydroxynon-3-en-2-yl]carbamate
• CAS: 133626-01-4
• 化学式: C₁₄H₂₇NO₃
• 分子量: 257.373
• InChiKey: DPCCIOJQBLBDLJ-PRDAAYKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-(S)-N-Boc-2-amino-3-nonenol 、 甲氧基-三氟甲基苯 生成 [(Z,2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]non-3-enyl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  BEAULIEU, PIERRE L.;DUCEPPE, JEAN-SIMON;JOHNSON, CAROLYNE, J. ORG. CHEM., 56,(1991) N3, C. 4196-4204

  摘要：

  DOI：
• 作为产物：
  描述：

  hexylidenetriphenylphosphoran 在 Dowex 50W strong H⁺ resin 、 水 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 生成 (Z)-(S)-N-Boc-2-amino-3-nonenol
  参考文献：
  名称：

  Synthesis of chiral vinylglycines

  摘要：

  (R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8. Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (> 95% ee) and double-bond geometry. D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives beta,gamma-unsaturated amino acids with the L configuration. The double-bond geometry is controlled by the nature of the phosphorous ylide employed. The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.

  DOI：

  10.1021/jo00013a023

文献信息

• Synthesis of the C10–C24 fragment of (+)-cannabisativine
  作者：Srivari Chandrasekhar、Bhoopendra Tiwari

  DOI：10.1016/j.tetasy.2009.07.037

  日期：2009.8

  The Stereoselective synthesis of the C10-C24 fragment of(+)-cannabisativine has been achieved. The key steps involved in this strategy are the Sharpless asymmetric dihydroxylation, the diastereoselective allylation of an imine, and the ring closing metathesis (RCM). (C) 2009 Elsevier Ltd. All rights reserved.
• BEAULIEU, PIERRE L.;DUCEPPE, JEAN-SIMON;JOHNSON, CAROLYNE, J. ORG. CHEM., 56,(1991) N3, C. 4196-4204
  作者：BEAULIEU, PIERRE L.、DUCEPPE, JEAN-SIMON、JOHNSON, CAROLYNE

  DOI：——

  日期：——
• Synthesis of chiral vinylglycines
  作者：Pierre L. Beaulieu、Jean Simon Duceppe、Carolyne Johnson

  DOI：10.1021/jo00013a023

  日期：1991.6

  (R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8. Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (> 95% ee) and double-bond geometry. D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives beta,gamma-unsaturated amino acids with the L configuration. The double-bond geometry is controlled by the nature of the phosphorous ylide employed. The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.