N-(2-Iodophenyl)-α-(diethoxyphosphinyl)acetamide | 152302-94-8

• 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-(2-Iodophenyl)-α-(diethoxyphosphinyl)acetamide
• 英文别名: diethyl [(2-iodophenyl)carbamoyl]methylphosphonate；2-diethoxyphosphoryl-N-(2-iodophenyl)acetamide
• CAS: 152302-94-8
• 化学式: C₁₂H₁₇INO₄P
• 分子量: 397.15
• InChiKey: LTJKGMMHUMTBQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  493.2±30.0 °C(Predicted)
• 密度：
  1.604±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  N-(2-Iodophenyl)-α-(diethoxyphosphinyl)acetamide 在 palladium on activated charcoal copper(l) iodide 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.83h， 生成 2,2'-<(2S^*,4S^*)-2,4-Pentanediyl>bibenzoxazole
  参考文献：
  名称：

  Copper(I) salt-mediated arylation of phosphinyl-stabilized carbanions and synthetic application to heterocyclic compounds

  摘要：

  The copper-mediated reaction of phosphinyl-stabilized carbanions 2a-c with aryl halides 1a-i in DMF or HMPA produced (arylmethyl)phosphonates 3-11 in good yields. Similar treatment of N-(2-iodophenyl)- and N-(2-iodophenyl)-N-methyl-alpha-(diethoxyphosphinyl)acetamides (12 and 14) led to 2-[(diethoxyphosphinyl)methyl]benzoxazole (13) and 1-methyl-3-(diethoxyphosphinyl)oxindole (15) in 71 and 85% yields, respectively. 4-(Ethoxycarbonyl)-3,4-dihydroisoquinoline N-oxide (33) was synthesized by the reaction of ethyl alpha-(o-formylphenyl)acrylate (31), derived from 6 and paraformaldehyde,with hydroxylamine. The cycloaddition of 33 to olefins such as dimethyl maleate, methyl acrylate, and styrene was studied.

  DOI：

  10.1021/jo00077a018
• 作为产物：
  描述：

  2-碘苯胺 在 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 N-(2-Iodophenyl)-α-(diethoxyphosphinyl)acetamide
  参考文献：
  名称：

  （±）-Rhazinal的形式全合成：评估自由基方法

  摘要：

  摘要 我们描述了外消旋的天然产物鼠李糖苷的正式全合成，方法是将最近报道的四氢吲哚嗪中间体快速合成成由Trauner报道的环化前体。合成着重于功能基团的早期和趋同引入，同时描述了该方法遇到的合成挑战。 我们描述了外消旋的天然产物鼠李糖苷的正式全合成，方法是将最近报道的四氢吲哚嗪中间体快速合成成由Trauner报道的环化前体。合成着重于功能基团的早期和趋同引入，同时描述了该方法遇到的合成挑战。

  DOI：

  10.1055/s-0036-1588956

文献信息

• Tandem Horner–Wadsworth–Emmons/Heck procedures for the preparation of 3-alkenyl-oxindoles: the synthesis of Semaxanib and GW441756
  作者：Jana Lubkoll、Alessia Millemaggi、Alexis Perry、Richard J.K. Taylor

  DOI：10.1016/j.tet.2010.03.018

  日期：2010.8

  developed to provide rapid access to 3-alkenyl-oxindoles from α-halo-anilides. This one-pot microwave accelerated process proceeds with catalytic palladium(II) acetate or tetrakis(triphenylphosphine)palladium, and has been used to prepare a range of adducts derived from aromatic, heteroaromatic and aliphatic aldehydes. The procedures can be used to prepare N-unprotected oxindoles directly and the applicability

  已经开发了一个串联序列，涉及霍纳-沃兹沃思-埃蒙斯（HWE）烯化反应，然后进行钯催化的分子内Heck反应，以提供从α-卤代苯胺快速获得3-烯基-氧吲哚的途径。这种一锅微波加速方法是使用乙酸乙酸钯（II）或四（三苯基膦）钯催化的，已用于制备一系列衍生自芳族，杂芳族和脂族醛的加合物。该方法可用于直接制备N-未保护的羟吲哚，并且该方法的适用性通过一锅合成塞马克尼（一种血管生成信号抑制剂）和GW441756（一种氮杂-羟吲哚Trk A抑制剂）来建立。
• Explorations in Organic Chemistry Leading to the Total Synthesis of (±)-Gelsemine
  作者：Fay W. Ng、Hong Lin、Samuel J. Danishefsky

  DOI：10.1021/ja0204675

  日期：2002.8.1

  The total synthesis of (+/-)-gelsemine (1) is described. A defining phase of the effort involved recourse to a strategic oxetane ring (see compound 25). It was constructed anticipating an intramolecular displacement of the carbon (C17)-oxygen (O4) bond (see product 48). A key intermediate in the stereospecific elaboration of the oxetane linkage was enone 22, which was susceptible to two beta-face attacks

  描述了 (+/-)-gelsemine (1) 的全合成。努力的一个决定性阶段涉及求助于战略氧杂环丁烷环（见化合物 25）。它的构建预期碳 (C17)-氧 (O4) 键的分子内置换（见产物 48）。氧杂环丁烷键的立体特异性加工中的一个关键中间体是烯酮 22，它容易受到导致 24 和 25 的两次 β 面攻击。在构建桥头堡 (C20) 和螺苯胺 (C7) 时采用了三个 sigmatropic 重排) 前往gelsemine 的第四纪中心。
• Synthesis and evaluation of 3-ylideneoxindole acetamides as potent anticancer agents
  作者：Chun-Tang Chiou、Wei-Chun Lee、Jiahn-Haur Liao、Jing-Jy Cheng、Lie-Chwen Lin、Chih-Yu Chen、Jen-Shin Song、Ming-Hsien Wu、Kak-Shan Shia、Wen-Tai Li

  DOI：10.1016/j.ejmech.2015.04.062

  日期：2015.6

  Indirubin, an active component in the traditional Chinese medicine formula Danggui Longhui Wan, shows promising anticancer effects. Meisoindigo is an analog derived from indirubin, which is less toxic and appears to be even more potent against cancer. In considering meisoindigo as a structural template for the development of new drugs, we designed and synthesized a series of 3-ylideneoxindole acetamides as novel anticancer agents. The acetamides were then evaluated for in vitro and in vivo anticancer activities. The 3-ylideneoxindole acetamides were found to have better anticancer activity than was indirubin-3'-oxime in several cancer cell lines and also displayed a spectrum of activity similar to that of the drug candidate roscovitine, a CDK inhibitor. Among the 3-ylideneoxindole acetamides, compound 10 showed particularly good efficacy. Cell cycle analysis further revealed that compound 10 arrested cells in the G1 phase and caused an increase in the sub-G1 population, indicating that the apoptosis pathway had been induced. In addition, exposure of cells to compound 10 led to the upregulation of the cell-cycle regulator cyclin D1, which was sustained at a high level. In contrast, the same compound induced a short-term elevation in the level of cyclin E, which was followed by a rapid decrease and the attenuation of Rb phosphorylation. Furthermore, a docking model suggests that compound 10 binds to the active site of CDK4. In testing the therapeutic potency of compound 10 on CT26-xenografted BALB/c mice, a significant reduction in tumor size comparable to that of cisplatin was found when administrated via the i.p. route. The mice presented no loss of body weight, indicating that this compound possesses low toxicity. In the future, we are planning in vivo investigations of these new active anticancer agents to better elucidate active mechanisms at the cellular level and thus benefit the development of anticancer therapies. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Minami Toru, Isonaka Takeshi, Okada Yoshiharu, Ichikawa Junji, J. Org. Chem, 58 (1993) N 25, S 7009-7015
  作者：Minami Toru, Isonaka Takeshi, Okada Yoshiharu, Ichikawa Junji

  DOI：——

  日期：——