N-ethyl-N-(2-iodobenzyl)ethanamine | 99558-03-9

• 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: N-ethyl-N-(2-iodobenzyl)ethanamine
• 英文别名: 1-(2-iodobenzyl)-1,1-diethylamine；N,N-diethyl-2-iodobenzylamine；NN-diethyl-o-iodobenzylamine；ortho-C6H4I(CH2N(C2H5)2)；Diethyl[(2-iodophenyl)methyl]amine；N-ethyl-N-[(2-iodophenyl)methyl]ethanamine
• CAS: 99558-03-9
• 化学式: C₁₁H₁₆IN
• mdl: MFCD06797847
• 分子量: 289.159
• InChiKey: XQFQHCGPQLYBOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-ethyl-N-(2-iodobenzyl)ethanamine 在 盐酸 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 1.0h， 生成 11-hydroxy-6H-isoindolo<2,1-a>indol-11-one
  参考文献：
  名称：

  Hooper, Malcolm; Imam, S. Haider, Journal of the Chemical Society. Perkin transactions I, 1985, p. 1583 - 1588

  摘要：

  DOI：
• 作为产物：
  描述：

  2-碘代甲苯 以 四氢呋喃 为溶剂， 生成 N-ethyl-N-(2-iodobenzyl)ethanamine
  参考文献：
  名称：

  Hooper, Malcolm; Imam, S. Haider, Journal of the Chemical Society. Perkin transactions I, 1985, p. 1583 - 1588

  摘要：

  DOI：

文献信息

• Kinetics of the Oxidative Addition ofortho-Substituted Aryl Halides to Palladium(0) Complexes
  作者：Mouad Alami、Christian Amatore、Samia Bensalem、Abdelharim Choukchou-Brahim、Anny Jutand

  DOI：10.1002/1099-0682(200109)2001:10<2675::aid-ejic2675>3.0.co;2-j

  日期：2001.9

  participate in the oxidative addition by a preliminary complexation of the active Pd0(PPh3)2 or Pd0(dppp) complex. The observed decelerating effect induced by the ortho substituents is due to steric hindrance and electronic donor effects and is less important for aryl bromides than for aryl iodides; ortho-substituted aryl iodides remain more reactive than ortho-substituted aryl bromides for both ligands

  邻位取代芳基卤化物氧化加成的速率常数，o-ZCH2-C6H4-X [X = I, Br; Z = OMe, NEt2, N(CH2)5] 到 Pd0(PPh3)4 或 Pd0(dba)(dppp) 从 Pd0(dba)2 和 1 equiv 生成。dppp 的确定。邻位取代的芳基卤化物的氧化加成比相应的未取代或间位取代的芳基卤化物的氧化加成慢。此处研究的邻位取代基不通过活性 Pd0(PPh3)2 或 Pd0(dppp) 复合物的初步络合参与氧化加成。观察到的由邻位取代基引起的减速效应是由于空间位阻和电子供体效应，对于芳基溴化物不如芳基碘化物重要；对于配体 PPh3 和 dppp，邻位取代芳基碘化物比邻位取代芳基溴化物更具反应性。
• Radioiodinated analogs of xylamine: N-(2-chloroethyl)-N-ethyl-2-[125I]iodobenzylamine and N,N-diethyl-2-[125I]iodobenzylamine as potential tools for monoamine uptake exploration by spect
  作者：C. Branger、L. Garreau、Y. Frangin、S. Chalon、P. Dubois、A.-M. Dognon、J.-E. Ombetta-Goka、J.-C. Besnard、D. Guilloteau

  DOI：10.1002/jlcr.2580360711

  日期：1995.7

  In order to improve the scintigraphy and radiotherapy of neuroendocrine tumors we synthesized two radioiodinated benzylamines [N-(2-chloroethyl)-N-ethyl-2-[125I]iodobenzylamine and N,N-diethyl-2-[125I]iodobenzylamine], analogs of xylamine [N-(2-chloroethyl)-N-ethyl-2-methylbenzylamine]. Xylamine is an irreversible inhibitor of uptake and accumulation of noradrenaline. The two unlabelled iodinated derivatives [N-(2-chloroethyl)-N-ethyl-2-iodobenzylamine and N,N-diethyl-2-iodobenzylamine] were synthesized, purified and checked by HPLC, NMR and mass spectrography. Their affinity for the noradrenaline transporter was determined in vitro on rat brain membrane homogenates with [3H]nisoxetine. Radioiodination was performed by iodide for bromide nucleophilic exchange from brominated precursors. The N,N-diethyl-2-[125I]iodobenzylamine was obtained directly from N,N-diethyl-2-bromobenzylamine. Radiosynthesis of N-(2-chloroethyl)-N-ethyl-2-[125I]iodobenzylamine required three steps. A new brominated precursor [N-ethyl-N-(2-bromobenzyl)glycine ethyl ester] which was stable for radiolabelling and suitable for reduction to N-(2-hydroxyethyl)-N-cthyl-2-[125I]iodobenzylamine was synthesized. N-(2-Hydroxyethyl)-N-ethyl-2-[125I]iodobenzylamine was converted to N-(2-chloroethyl)-N-ethyl-2-[125I]iodobenzylamine in the presence of an excess of thionyl chloride. Radioiodinated derivatives were purified and checked by HPLC.

  为了改进神经内分泌肿瘤的闪烁成像和放射治疗，我们合成了两种放射性碘化苄胺[N-（2-氯乙基）-N-乙基-2-[125I]碘苄胺和 N,N-二乙基-2-[125I]碘苄胺]，它们是二甲胺[N-（2-氯乙基）-N-乙基-2-甲基苄胺]的类似物。二甲胺是去甲肾上腺素摄取和蓄积的不可逆抑制剂。我们合成并纯化了两种未标记的碘化衍生物[N-（2-氯乙基）-N-乙基-2-碘苄胺和 N,N-二乙基-2-碘苄胺]，并通过高效液相色谱法、核磁共振法和质谱法对其进行了检测。体外用[3H]尼索西汀测定了它们对大鼠脑膜匀浆中去甲肾上腺素转运体的亲和力。放射性碘化是通过碘化物与溴化前体的亲核交换进行的。N,N-二乙基-2-[125I]碘苄胺是直接从 N,N-二乙基-2-溴苄胺中获得的。N-(2-氯乙基)-N-乙基-2-[125I]碘苄胺的放射合成需要三个步骤。我们合成了一种新的溴化前体[N-乙基-N-(2-溴苄基)甘氨酸乙酯]，它对放射性标记稳定，适合还原成 N-(2-羟乙基)-N-辛基-2-[125I]碘苄胺。在过量亚硫酰氯的存在下，N-(2-羟乙基)-N-乙基-2-[125I]碘苄胺转化为 N-(2-氯乙基)-N-乙基-2-[125I]碘苄胺。放射性碘化衍生物经高效液相色谱法纯化和检测。
• α-Alkylation of amines via a 1,5-hydrogen shift
  作者：Kjell Undheim、Lorenzo Williams

  DOI：10.1039/c39940000883

  日期：——

  Radicals derived from N-(2-iodobenzyl)‘protected’ amines undergo a 1,5-hydrogen shift to give more stable α-amino radicals, which can be subsequently trapped by electron deficient alkenes.

  衍生自N-（2-碘苄基）'保护的'胺的自由基进行1,5-氢转移，得到更稳定的α-氨基，这些自由基随后可被缺乏电子的烯烃捕获。
• Yoshikai, Naohiko; Mieczkowski, Adam; Matsumoto, Arimasa, Journal of the American Chemical Society, 2010, vol. 132, p. 5568 - 5569
  作者：Yoshikai, Naohiko、Mieczkowski, Adam、Matsumoto, Arimasa、Ilies, Laurean、Nakamura, Eiichi

  DOI：——

  日期：——
• Generation and alkylation of carbanions .alpha. to the nitrogen of amines by a new metallation procedure
  作者：Masahiro Murakami、Minoru Hayashi、Yoshihiko Ito

  DOI：10.1021/jo00029a001

  日期：1992.1

  Treatment of a tertiary amine having a pendent o-iodobenzyl group on nitrogen with SmI2 generates alpha-amino organosamarium, which reacts with electrophiles giving the corresponding C-C bound formation products in good yield.