Acetic acid 1-(tert-butoxycarbonylamino-methyl)-allyl ester | 134676-37-2

• 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: Acetic acid 1-(tert-butoxycarbonylamino-methyl)-allyl ester
• 英文别名: 1-[(2-Methylpropan-2-yl)oxycarbonylamino]but-3-en-2-yl acetate
• CAS: 134676-37-2
• 化学式: C₁₁H₁₉NO₄
• 分子量: 229.276
• InChiKey: YASQRXOQHMYGPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  Acetic acid 1-(tert-butoxycarbonylamino-methyl)-allyl ester 在 sodium periodate 、 N-甲基吲哚酮 、 sodium carbonate 、 锌 、 二溴三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 为溶剂， 反应 3.67h， 生成 Boc-Glyψ-D,L-Trp-OBn
  参考文献：
  名称：

  Novel methodology for the synthesis of trans-alkene dipeptide isosteres

  摘要：

  Natural amino acids were converted to the corresponding allylic alcohols A, from which key precursors C were obtained via a three-step sequence [(a) Ac2O/Py or CbzOSu/Et3N/DMAP; (b) NMO/NaIO4/OsO4(cat.); (c) Ph3P = CR2CO2Bn]. The allylic alcohols D were further transformed to the desired pseudodipeptides I through the corresponding bromo derivatives E via a reductive deconjugation process.

  DOI：

  10.1021/jo00006a027
• 作为产物：
  描述：

  2-oxo-5-ethenyloxazolidine-3-carboxylic acid tert-butyl ester 、 乙酸酐 在 4-二甲氨基吡啶 、 TEA 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到Acetic acid 1-(tert-butoxycarbonylamino-methyl)-allyl ester
  参考文献：
  名称：

  A new approach to the synthesis of the carbon framework of SC-84536, an inducible nitric oxide synthase inhibitor

  摘要：

  SC-84536, a selective inhibitor of inducible nitric oxide synthase (iNOS), is targeted for the treatment of osteoarthritis, neuropathic pain, and asthma. The initial technology for constructing this molecule was acceptable only for the preparation of small quantities of material, but was not practical for larger scale work. This Letter describes our effort toward developing an alternative synthetic route for the carbon framework of SC-84536. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.083

文献信息

• Amide bond surrogates: A general synthetic route to trans carbon-carbon double bono isosteres.
  作者：Youe-Kong Shue、George M. Carrera、Alex M. Nadzan

  DOI：10.1016/s0040-4039(00)95477-7

  日期：1987.1

  A practical synthesis toward trans double bond replacements of amide bond pseudo-peptides has been accomplished. This methodology provides a general route to a wide range of modified peptide analogs which may have biological significance.

  已经完成了对酰胺键伪肽的反式双键置换的实用合成。该方法学提供了获得广泛的修饰的肽类似物的一般途径，这些修饰的肽类似物可能具有生物学意义。
• Tetrapeptide type-B CCK receptor ligands
  申请人：ABBOTT LABORATORIES

  公开号：EP0405506A1

  公开（公告）日：1991-01-02

  A tetrapeptide type-B CCK receptor ligand of the formula A-B-C-D or a pharmaceutically acceptable salt thereof, which is useful for treating central nervous system disorders, substance abuse, gastrointestinal disorders, endocrine disorders, eating-related disorders and treatment of shock, respiratory and cardiocirculatory insufficiencies.

  式中的四肽-B 型 CCK 受体配体 A-B-C-D 或其药学上可接受的盐，可用于治疗中枢神经系统疾病、药物滥用、胃肠功能紊乱、内分泌失调、进食相关疾病以及休克、呼吸和心血管功能不全的治疗。
• US5340802A
  申请人：——

  公开号：US5340802A

  公开（公告）日：1994-08-23