氨甲酸,[2,3,4,7-四氢-2-羰基-1-(苯基甲基)-1H-吖庚英-3-基]-,1,1-二甲基乙基酯 | 183867-13-2

• 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
• 中文名称: 氨甲酸,[2,3,4,7-四氢-2-羰基-1-(苯基甲基)-1H-吖庚英-3-基]-,1,1-二甲基乙基酯
• 英文名称: (+/-)-tert-butyl (1-benzyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl)carbamate
• 英文别名: tert-butyl 1-benzyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate；tert-butyl N-(1-benzyl-7-oxo-5,6-dihydro-2H-azepin-6-yl)carbamate
• CAS: 183867-13-2
• 化学式: C₁₈H₂₄N₂O₃
• 分子量: 316.4
• InChiKey: AWXWPPXUJSMPLO-UHFFFAOYSA-N

物化性质

• 沸点：
  502.4±50.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氨甲酸,[2,3,4,7-四氢-2-羰基-1-(苯基甲基)-1H-吖庚英-3-基]-,1,1-二甲基乙基酯 在 Oxone 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 18.0h， 以63%的产率得到tert-butyl N-(3-benzyl-4-oxo-8-oxa-3-azabicyclo[5.1.0]octan-5-yl)carbamate
  参考文献：
  名称：

  Synthesis of amino acid derived seven-membered lactams by RCM and their evaluation against HIV protease

  摘要：

  A versatile synthesis of hydroxylated and epoxy 1-azepin 2-ones substituted at N1, C-3 and C-4 or C-7 has been developed. The sequence involves ring-closing metathesis of an amino acid derived diene amide, followed by either epoxidation or dihydroxylation, of the resulting alkene. Assay of the product epoxides (10, 18, 25) and diols (9a, 17, 24) against HIV protease reveals micromolar inhibition. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.009
• 作为产物：
  描述：

  N-烯丙基苄胺 在 Grubbs catalyst first generation N-甲基吡咯烷酮 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 氨甲酸,[2,3,4,7-四氢-2-羰基-1-(苯基甲基)-1H-吖庚英-3-基]-,1,1-二甲基乙基酯
  参考文献：
  名称：

  Synthesis of amino acid derived seven-membered lactams by RCM and their evaluation against HIV protease

  摘要：

  A versatile synthesis of hydroxylated and epoxy 1-azepin 2-ones substituted at N1, C-3 and C-4 or C-7 has been developed. The sequence involves ring-closing metathesis of an amino acid derived diene amide, followed by either epoxidation or dihydroxylation, of the resulting alkene. Assay of the product epoxides (10, 18, 25) and diols (9a, 17, 24) against HIV protease reveals micromolar inhibition. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.009

文献信息

• Synthesis of Fused 3-Aminoazepinones via Trapping of a New Class of Cyclic Seven-Membered Allenamides with Furan
  作者：Ben Schurgers、Ben Brigou、Zofia Urbanczyk-Lipkowska、Dirk Tourwé、Steven Ballet、Frank De Proft、Guy Van Lommen、Guido Verniest

  DOI：10.1021/ol501529z

  日期：2014.7.18

  reaction of furan with cyclic allenamides. These reactive intermediates are the first examples of cyclic seven-membered allenamides and were prepared starting from N-(2-chloroallyl)-2-allylglycine derivatives via ring-closing metathesis followed by dehydrochlorination. The trapping of the intermediate cycloallene with furan occurred endo- and regioselectively and provided a convenient entry into new building

  通过呋喃与环状烯丙酰胺的原位Diels-Alder反应合成了新型三环四氢a庚酮。这些反应性中间体是环状七元烯丙酰胺的第一个实例，由N-（2-氯烯丙基）-2-烯丙基甘氨酸衍生物经闭环易位，然后进行脱氯化氢反应制得。中间体环戊烯与呋喃的捕集发生在区域内和区域选择性，为药物化学的新组成部分提供了便利。使用量子化学计算证实了环加成的非对映选择性。
• Solid phase ring-closing metathesis: Cyclization/cleavage approach towards a seven membered cycloolefin
  作者：Jan H. van Maarseveen、Jack A.J. den Hartog、Victor Engelen、Emil Finner、Geb Visser、Chris G. Kruse

  DOI：10.1016/0040-4039(96)01881-3

  日期：1996.11

  The application of solid phase ring-closing metathesis (RCM) in a cyclization/cleavage strategy was demonstrated for the first time by the successful synthesis of the seven membered cycloolefin 4. Probably due to intermolecular metathetical dimerizations at the resin, 4 could not be obtained in higher yields than 54%.

  通过成功合成七元环烯烃4首次证明了固相开环复分解（RCM）在环化/裂解策略中的应用。可能由于树脂间的分子间复分解二聚，不能以高于54％的高收率获得4。
• A second generation solid phase approach to Freidinger lactams: Application of Fukuyama's amine synthesis and cyclative release via ring closing metathesis
  作者：Anthony D. Piscopio、John F. Miller、Kevin Koch

  DOI：10.1016/s0040-4039(98)00374-8

  日期：1998.4

  A high-speed solid phase synthesis of Freidinger lactams was accomplished using a novel variant of Fukuyama's amine synthesis and ring closing metathesis-promoted cyclative cleavage as key steps. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Ring closing metathesis in organic synthesis: Evolution of a high speed, solid phase method for the preparation of β-turn mimetics
  作者：Anthony D Piscopio、John F Miller、Kevin Koch

  DOI：10.1016/s0040-4020(99)00300-2

  日期：1999.7

  Complimentary solid phase syntheses of the Freidinger lactam class of p-turn mimetics have been developed using ring closing metathesis as both the key carbon-carbon bond forming step and the cyclative cleavage mechanism. Solid phase variants of the Fukuyama-Mitsunobu process were utilized as pad of a rapid three-step sequence to construct immobilized lactam precursors, an alternative solid phase process is offered which utilizes an Ugi/ring closing metathesis reaction tandem to deliver the desired compounds in two synthetic operations. (C) 1999 Published by Elsevier Science Ltd, All rights reserved.
• Synthesis of amino acid derived seven-membered lactams by RCM and their evaluation against HIV protease
  作者：Shazia Zaman、Pietro Campaner、Andrew D. Abell

  DOI：10.1016/j.bmc.2006.09.009

  日期：2006.12

  A versatile synthesis of hydroxylated and epoxy 1-azepin 2-ones substituted at N1, C-3 and C-4 or C-7 has been developed. The sequence involves ring-closing metathesis of an amino acid derived diene amide, followed by either epoxidation or dihydroxylation, of the resulting alkene. Assay of the product epoxides (10, 18, 25) and diols (9a, 17, 24) against HIV protease reveals micromolar inhibition. (c) 2006 Elsevier Ltd. All rights reserved.