bromo<(S)-<1-(1-naphthyl)ethyl>carbamoyl>methane | 197566-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: bromo<(S)-<1-(1-naphthyl)ethyl>carbamoyl>methane
• 英文别名: (S)-2-bromo-N-(1-(naphthalen-1-yl)ethyl)acetamide；2-bromo-N-[(1S)-1-naphthalen-1-ylethyl]acetamide
• CAS: 197566-54-4
• 化学式: C₁₄H₁₄BrNO
• 分子量: 292.175
• InChiKey: ZNTOYDMNBUDJII-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  bromo<(S)-<1-(1-naphthyl)ethyl>carbamoyl>methane 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 (S)-1-(1-naphthylethyl)carbamoylmethyl-1'-(3-bromopropyl)-4,4'-bipyridinium dibromide
  参考文献：
  名称：

  光学活性双紫罗碱单价阳离子在水溶液中歧化的手性识别

  摘要：

  合成了含有 1-(1-萘基)-、1-苯基-和 1-环己基乙胺的光学活性双紫精。由单电子还原产生的单自由基三聚体的歧化在 (S,R)-异构体中比在 (S,S)- 和 (R,R)-异构体中更容易发生。歧化由双自由基指示剂的两个紫罗碱自由基单元之间的分子内缔合中手性取代基的空间体积控制。

  DOI：

  10.1246/cl.1997.941
• 作为产物：
  描述：

  (S)-(-)-1-(1-萘基)乙胺 、 溴乙酰溴 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 bromo<(S)-<1-(1-naphthyl)ethyl>carbamoyl>methane
  参考文献：
  名称：

  A Peptoid Square Helix via Synergistic Control of Backbone Dihedral Angles

  摘要：

  The continued expansion of the fields of macromolecular chemistry and nanoscience has motivated the development of new secondary structures that can serve as architectural elements of innovative materials, molecular machines, biological probes, and even commercial medicines. Synthetic foldamers are particularly attractive systems for developing such elements because they are specifically designed to facilitate synthetic manipulation and functional diversity. However, relatively few predictive design principles exist that permit both rational and modular control of foldamer secondary structure, while maintaining the capacity for facile diversification of displayed functionality. We demonstrate here that the synergistic application of two such principles in the design of peptoid foldamers yields a new and unique secondary structure that we term an "eta-helix" due to its repeating turns, which are highly reminiscent of peptide beta-turns. Solution-phase structures of eta-helices were obtained by simulated annealing using NOE-derived distance restraints, and the NMR spectra of a series of designed eta-helices were altogether consistent with the primary adoption of this structure. The structure is resilient to solvent and temperature changes, and accommodates diversification without requiring postsynthetic manipulation. The unique shape, broad structural stability, and synthetic accessibility of eta-helices could facilitate their utilization in a wide range of applications.

  DOI：

  10.1021/jacs.7b02319

文献信息

• Syntheses, Characterizations, and Redox Behavior of Optically Active Viologens and Bisviologens
  作者：Keiichi Tsukahara、Junko Kaneko、Tomoko Miyaji、Kaya Abe、Maki Matsuoka、Tomoko Hara、Tomoaki Tanase、Shigenobu Yano

  DOI：10.1246/bcsj.72.139

  日期：1999.1

  Optically active viologens, containing [1-(1-naphthyl)-, 1-phenyl-, and 1-cyclohexylethyl]carbamoylmethyl groups, have been synthesized and characterized. The redox behavior of the chiral viologens was studied compared with achiral viologens. The monoviologens containing naphthyl groups show an intermolecular charge-transfer interaction between the bipyridinium and naphthyl groups in aqueous solution

  已合成并表征了含有 [1-(1-萘基)-、1-苯基-和 1-环己基乙基] 氨基甲酰基甲基的光学活性紫罗碱。与非手性紫精相比，研究了手性紫精的氧化还原行为。含有萘基的单紫罗碱在水溶液中显示出联吡啶鎓和萘基之间的分子间电荷转移相互作用。缔合常数取决于紫精的手性，并且在 (S,S)- 和 (R,R)-异构体中比在 (R,S)-one 中更大。还合成并表征了手性双紫精，其中两个紫精单元与三亚甲基链相连。尽管双吡啶鎓和双紫精的紫精单元之间的分子间电荷转移相互作用在溶液中非常弱，这种相互作用在固态下可明显观察到，这已通过 X 射线晶体学证实。由双紫原不成比例的单电子还原产生的单自由基三聚体...
• Stereoselective Photoinduced Electron Transfer of Zinc Myoglobin with Optically Active Viologens
  作者：Keiichi Tsukahara、Chieko Kimura、Junko Kaneko、Tomoko Hara

  DOI：10.1246/cl.1994.2377

  日期：1994.12

  The excited triplet state of zinc myoglobin was preferentially quenched by (S,S)-isomers of optically active viologens, 1,1′-bis(1-phenylethylcarbamoylmethyl)-4,4′-bipyridimum (OAV2+) and 1,1′-bis(1-(1-naphthyl)ethylcarbamoylmethyl)-4,4′-bipyridinium (NOAV2+) ions: kq((S,S)-)/kq((R,R)-) = 1.5 for NOAV2+ and 1.3 for OAV2+ at 25 °C and an ionic strength of 0.02 mol dm−3.

  锌肌红蛋白的激发三重态优先被光学活性病毒素的(S,S)异构体--1、1′-双(1-苯基乙基氨基甲酰甲基)-4,4′-联吡啶(OAV2+)和 1,1′-双(1-(1-萘基)乙基氨基甲酰甲基)-4,4′-联吡啶(NOAV2+)离子优先淬灭：kq((S,S)-)/kq((R,R)-)在 25 °C 和离子强度为 0.02 mol dm-3 时，NOAV2+ 的 kq((S,S)-)/kq((R,R)-) = 1.5，OAV2+ 的 kq((S,S)-)/kq((R,R)-) = 1.3。