benzyl 2-methyl-4-oxohex-5-en-3-ylcarbamate | 1332641-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 2-methyl-4-oxohex-5-en-3-ylcarbamate
• 英文别名: benzyl N-[(3S)-2-methyl-4-oxohex-5-en-3-yl]carbamate
• CAS: 1332641-55-0
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: PVHTUVLHUZUUIC-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 2-methyl-4-oxohex-5-en-3-ylcarbamate 、 (乙氧基羰基甲基)二甲基溴化硫鎓 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 为溶剂， 反应 19.0h， 以78%的产率得到ethyl 2-((S)-2-(benzyloxycarbonylamino)-3-methylbutanoyl)-cyclopropanecarboxylate
  参考文献：
  名称：

  Three-Step Synthesis of Cyclopropyl Peptidomimetics

  摘要：

  An efficient approach to novel cyclopropyl peptidomimetics has been developed. The synthetic route involves a cyclopropanation using ethyl (dimethylsulfuranylidene)acetate (EDSA) as the key step and affords a cyclopropyl peptidomimetic core in three steps from protected amino acid Weinreb amides.

  DOI：

  10.1021/ol201828u
• 作为产物：
  描述：

  CBZ-L-缬氨酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 benzyl 2-methyl-4-oxohex-5-en-3-ylcarbamate
  参考文献：
  名称：

  Three-Step Synthesis of Cyclopropyl Peptidomimetics

  摘要：

  An efficient approach to novel cyclopropyl peptidomimetics has been developed. The synthetic route involves a cyclopropanation using ethyl (dimethylsulfuranylidene)acetate (EDSA) as the key step and affords a cyclopropyl peptidomimetic core in three steps from protected amino acid Weinreb amides.

  DOI：

  10.1021/ol201828u

文献信息

• Stereoselective cyclopropanations of amino-acid derived enones
  作者：Avraz Anwar、Holli Kerns、Taylor Orr、Jonathan Byrd、Zackary Fitzsimonds、Norma Dunlap

  DOI：10.1016/j.tetlet.2020.152552

  日期：2020.11

  Stereoselective cyclopropanation of a series of amino acid-derived enones to afford cyclopropyl keto-esters is reported, using a Michael-induced ring closure. The use of quinine and quinidine ether catalysts in the cyclopropanation step afforded the cyclopropyl keto-esters with high stereoselectivity. Results follow a consistent pattern, with the pseudoenantiomeric catalysts leading to opposite stereoselectivity

  据报道，使用迈克尔诱导的闭环，一系列氨基酸衍生的烯酮的立体选择性环丙烷化以提供环丙基酮酯。在环丙烷化步骤中使用奎宁和奎尼丁醚催化剂提供了具有高立体选择性的环丙基酮酯。结果遵循一致的模式，假对映体催化剂导致相反的立体选择性，从而可以合成顺式或反式非对映异构体。
• Synthesis of nitrocyclopropyl peptidomimetics
  作者：Norma K. Dunlap、Jacob Basham、Matthew Wright、Katrina Smith、Omar Chapa、Jihun Huang、Will Shelton、Yaroslav Yatsky

  DOI：10.1016/j.tetlet.2013.09.106

  日期：2013.11

  Nitrocyclopropanation of amino-acid derived enones has led to a series of cyclopropyl peptidomimetics suitable for further elaboration to compounds with the potential for biological activity. (C) 2013 Elsevier Ltd. All rights reserved.
• Three-Step Synthesis of Cyclopropyl Peptidomimetics
  作者：Norma Dunlap、Kevin R. Lankford、Anuradha Liyana Pathiranage、Jessica Taylor、Nikhil Reddy、Daniel Gouger、Phillip Singer、Kent Griffin、Joseph Reibenspies

  DOI：10.1021/ol201828u

  日期：2011.9.16

  An efficient approach to novel cyclopropyl peptidomimetics has been developed. The synthetic route involves a cyclopropanation using ethyl (dimethylsulfuranylidene)acetate (EDSA) as the key step and affords a cyclopropyl peptidomimetic core in three steps from protected amino acid Weinreb amides.