(-)-(2R)-tert-butyl 1-(methoxycarbonyl)pent-4-enylcarbamate | 221318-99-6

• 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: (-)-(2R)-tert-butyl 1-(methoxycarbonyl)pent-4-enylcarbamate
• 英文别名: methyl (2R)-[N-(tert-butoxycarbonyl)amino]hex-5-enoate；(R)-methyl 2-((tert-butoxycarbonyl)amino)hex-5-enoate；methyl (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hex-5-enoate
• CAS: 221318-99-6
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: MXDNEPDJMODRAI-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (-)-(2R)-tert-butyl 1-(methoxycarbonyl)pent-4-enylcarbamate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 Boc-D-Homoallylglycine
  参考文献：
  名称：

  Flexible Synthesis and Evaluation of Diverse Anti-Apicomplexa Cyclic Peptides

  摘要：

  A modular approach to synthesize anti-Apicomplexa parasite inhibitors was developed that takes advantage of a pluripotent cyclic tetrapeptide scaffold capable of adjusting appendage and skeletal diversities in only a few steps (one to three steps). The diversification processes make use of selective radical coupling reactions and involve a new example of a reductive carbon nitrogen cleavage reaction with SmI2. The resulting bioactive cyclic peptides have revealed new insights into structural factors that govern selectivity between Apicomplexa parasites such as Toxoplasma and Plasmodium and human cells.

  DOI：

  10.1021/jo4001492
• 作为产物：
  描述：

  2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 在 吡啶 、 碘 、 三苯基膦 、 copper(I) bromide 、 锌 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (-)-(2R)-tert-butyl 1-(methoxycarbonyl)pent-4-enylcarbamate
  参考文献：
  名称：

  钯催化邻碘苯胺与 N-Boc-N-甲基丙氨酰取代的乙醛和乙炔反应合成 d-Abrines

  摘要：

  一种新的策略，以Ñ -Boc- ñ -甲基-色氨酸（abrine衍生物）的开发依赖于邻iodoanilines的钯催化环12与任一Ñ -Boc- ñ -甲基-炔丙基甘氨酸16或醛11。两个11和16可以从制备d -丝氨酸。炔丙基甘氨酸16的替代途径利用甘氨酸亚胺17的对映选择性炔丙基化反应。

  DOI：

  10.1021/ol4009409

文献信息

• Combined application of organozinc chemistry and one-pot hydroboration–Suzuki coupling to the synthesis of amino acids
  作者：Arantxa Rodríguez、David D. Miller、Richard F. W. Jackson

  DOI：10.1039/b300536d

  日期：2003.3.13

  Hydroboration using 9-BBN-H of the protected enantiomerically pure but-3-enylglycine derivative 11, prepared by copper-catalysed allylation of the serine-derived organozinc reagent 1, followed by Suzuki coupling of the derived borane with a variety of aromatic halides, 2-bromopyridine and 2-bromopropene gives the protected amino acids 14a–l and 15. This method augments our previous methods for the synthesis of phenylalanine homologues.

  使用9-BBN-H对保护的手性纯的丁-3-烯基甘氨酸衍生物11进行氢硼化，该衍生物是通过铜催化的烯丙基化反应得到的，反应中使用了源自丝氨酸的有机锌试剂1，之后与多种芳香卤化物（如2-溴吡啶和2-溴丙烯）进行铃木偶联反应，得到保护的氨基酸14a-l和15。这种方法增强了我们之前合成苯丙氨酸同源物的策略。
• Asymmetric Synthesis of Fluorinated Amino Macrolactones through Ring-Closing Metathesis
  作者：Santos Fustero、Begoña Fernández、Juan F. Sanz-Cervera、Natalia Mateu、Silvia Mosulén、Rodrigo J. Carbajo、Antonio Pineda-Lucena、Carmen Ramírez de Arellano

  DOI：10.1021/jo701484w

  日期：2007.11.1

  The synthesis of new chiral fluorinated amino and azamacrolactones of types 1 and 2 is described. A ring-closing metathesis (RCM) reaction constitutes the key step in this methodology, which uses fluorinated amino alcohols 7 as starting materials. The influence of the CF2 group, which is located in the (x-position relative to the carbon bearing the amino group, on the efficiency of the RCM reaction is noteworthy. This method allows for the preparation of the desired fluorinated macrolactones in excellent yields.
• Flexible Synthesis and Evaluation of Diverse Anti-Apicomplexa Cyclic Peptides
  作者：Mariam Traoré、Flore Mietton、Danièle Maubon、Marine Peuchmaur、Flaviane Francisco Hilário、Rossimiriam Pereira de Freitas、Alexandre Bougdour、Aurélie Curt、Marjorie Maynadier、Henri Vial、Hervé Pelloux、Mohamed-Ali Hakimi、Yung-Sing Wong

  DOI：10.1021/jo4001492

  日期：2013.4.19

  A modular approach to synthesize anti-Apicomplexa parasite inhibitors was developed that takes advantage of a pluripotent cyclic tetrapeptide scaffold capable of adjusting appendage and skeletal diversities in only a few steps (one to three steps). The diversification processes make use of selective radical coupling reactions and involve a new example of a reductive carbon nitrogen cleavage reaction with SmI2. The resulting bioactive cyclic peptides have revealed new insights into structural factors that govern selectivity between Apicomplexa parasites such as Toxoplasma and Plasmodium and human cells.
• Synthesis of <scp>d</scp>-Abrines by Palladium-catalyzed Reaction of ortho-Iodoanilines with <i>N</i>-Boc-<i>N</i>-methylalanyl-substituted Acetaldehyde and Acetylene
  作者：Paulami Danner、Marius Morkunas、Martin E. Maier

  DOI：10.1021/ol4009409

  日期：2013.5.17

  N-Boc-N-methyl--tryptophans (abrine derivatives) was developed that relies on the palladium-catalyzed annulation of ortho-iodoanilines 12 with either N-Boc-N-methyl-propargylglycine 16 or aldehyde 11. Both 11 and 16 can be prepared from d-serine. An alternative route to propargylglycine 16 utilizes an enantioselective propargylation reaction of glycine imine 17.

  一种新的策略，以Ñ -Boc- ñ -甲基-色氨酸（abrine衍生物）的开发依赖于邻iodoanilines的钯催化环12与任一Ñ -Boc- ñ -甲基-炔丙基甘氨酸16或醛11。两个11和16可以从制备d -丝氨酸。炔丙基甘氨酸16的替代途径利用甘氨酸亚胺17的对映选择性炔丙基化反应。