4-碘-[2-(1-哌啶基)乙氧基l]苯 | 103808-68-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-碘-[2-(1-哌啶基)乙氧基l]苯
• 英文名称: 1-(2-(4-Iodophenoxy)ethyl)piperidine
• 英文别名: 4-[2-(piperidin-1-yl)-ethoxy]-iodobenzene；1-[2-(4-iodophenoxy)ethyl]piperidine
• CAS: 103808-68-0
• 化学式: C₁₃H₁₈INO
• mdl: MFCD11110470
• 分子量: 331.197
• InChiKey: OADCVVWLHQWRPD-UHFFFAOYSA-N

物化性质

• 沸点：
  381.0±27.0 °C(Predicted)
• 密度：
  1.468±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-碘-[2-(1-哌啶基)乙氧基l]苯 在 四(三苯基膦)钯 、 正丁基锂 、 tetra-N-butylammonium tribromide 、 potassium carbonate 、 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 苯 为溶剂， 生成 4-[2-fluoro-2-phenyl-1-[4-(2-piperidin-1-ylethoxy)phenyl]ethenyl]phenol
  参考文献：
  名称：

  Synthesis and growth inhibition activity of fluorinated derivatives of tamoxifen

  摘要：

  The design and synthesis of 11 fluorinated derivatives of tamoxifen are described. Growth inhibition values (GI(50)) on human HT-29, M21, MCF7, and MDA-MB-231 tumor cells are also reported. In general, the GI(50) values are similar or slightly higher than tamoxifen with the most active compound on MCF7 cell line having a GI(50) = 3.6 mu M. Surprisingly, as opposed to tamoxifen, both geometrical isomers behave similarly. We hypothesize that this behavior is due to in vitro isomerization of the compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.057
• 作为产物：
  描述：

  4-碘苯酚 、 1-(2-氯乙基)哌啶盐酸盐 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以77%的产率得到4-碘-[2-(1-哌啶基)乙氧基l]苯
  参考文献：
  名称：

  3-苯甲酰苯并[高效合成b ]噻吩和雷洛昔芬通过汞（II） -催化的环化的2-炔基苯基烷基亚砜

  摘要：

  分别通过关键中间体4-甲氧基苄基2-溴-4-甲氧基苯基亚砜（6）合成了独特的选择性雌激素受体调节剂雷洛昔芬（1）和抗微管蛋白剂2。发现与邻硫烷基芳基溴化物相比，邻位的亚磺酰基加速了芳基溴化物的Sonogashira偶联反应。因此，将化合物6与3,4,5-三甲氧基苯基乙炔偶联，然后通过汞催化的环化反应以79％的总收率得到化合物2。由化合物6分四步制备雷洛昔芬（1），并通过与1-三甲基甲硅烷基-2-（4-叔丁基二甲基甲硅烷氧基）苯基乙炔的偶合反应，汞催化的环化反应，烷基化和去甲基化。

  DOI：

  10.1016/j.tet.2018.03.067

文献信息

• Novel heteroatom containing tetracyclic derivatives as selective estrogen receptor modulators
  申请人：——

  公开号：US20040259915A1

  公开（公告）日：2004-12-23

  The present invention is directed to novel heteroatom containing tetracyclic derivatives, pharmaceutical compositions containing them, their use in the treatment and/or prevention of disorders mediated by one or more estrogen receptors and processes for their preparation. The compounds of the invention are useful in the treatment and/or prevention of disorders associated with the depletion of estrogen such as hot flashes, vaginal dryness, osteopenia and osteoporosis; hormone sensitive cancers and hyperplasia of the breast, endometrium, cervix and prostate; endometriosis, uterine fibroids, osteoarthritis and as contraceptive agents, alone or in combination with a progestogen or progestogen antagonist.

  本发明涉及新颖的含杂原子四环衍生物、含有它们的药物组合物、它们在治疗和/或预防由一个或多个雌激素受体介导的疾病中的应用，以及它们的制备方法。本发明的化合物在治疗和/或预防与雌激素耗竭相关的疾病中具有用途，例如热潮红、阴道干燥、骨量减少和骨质疏松症；激素敏感性癌症以及乳腺、子宫内膜、宫颈和前列腺的增生；子宫内膜异位症、子宫肌瘤、骨关节炎，以及作为避孕剂，单独使用或与孕激素或孕激素拮抗剂联合使用。
• Substrate‐Assisted, Transition‐Metal‐Free Diboration of Alkynamides with Mixed Diboron: Regio‐ and Stereoselective Access to <i>trans</i> ‐1,2‐Vinyldiboronates
  作者：Astha Verma、Russell F. Snead、Yumin Dai、Carla Slebodnick、Yinuo Yang、Haizhu Yu、Fu Yao、Webster L. Santos

  DOI：10.1002/anie.201700946

  日期：2017.4.24

  A substrate‐assisted diboration of alkynamides using the unsymmetrical pinacolato‐1,8‐diaminonaphthalenato diboron (pinBBdan) is described. The transition‐metal‐free reaction proceeds in a regio‐ and stereoselective fashion to exclusively afford trans‐vinyldiboronates in good to excellent yields. Notably, Bdan and Bpin are installed on the α‐ and β‐carbon atoms, respectively.

  本文介绍了使用不对称的频哪醇-1,8-二氨基萘萘二硼（pinBBdan）对炔酰胺进行底物辅助的硼氢化反应。无过渡金属的反应以区域选择性和立体选择性的方式进行，从而以高至优异的收率独家提供反式乙烯基二硼酸酯。值得注意的是，Bdan和Bpin分别安装在α-和β-碳原子上。
• Synthesis of Tetracyclic Heterocompounds as Selective Estrogen Receptor Modulators. Part 1. Process Development for Scale-up of 2,5,8-Substituted 5,11-Dihydrochromeno[4,3-<i>c</i>]chromene Derivatives
  作者：Xun Li、Michael Reuman、Ronald K. Russell、Richard Adams、Robert Ma、Sandra Beish,、Shawn Branum、Scott Youells、Jerry Roberts、Nareshkumar Jain、Ramesh Kanojia、Zhihua Sui

  DOI：10.1021/op700020f

  日期：2007.5.1

  compounds are novel selective estrogen receptor modulators (SERMs). A reproducible and nonchromatographic process was developed to prepare multihundred gram quantities of 5-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-5,11-dihydrochromeno[4,3-c]chromene-2,8-diyl-bis(2,2-dimethylpropanoate) (14). The overall yield of this 11-step synthesis was improved from 0.17% to 7.1% after three scale-up campaigns.

  不对称的苯并吡喃并苯并吡喃化合物是新型的选择性雌激素受体调节剂（SERM）。开发了一种可重现的非色谱方法，以制备数百克数量的5-（4-（2-（2-哌啶-1-基）乙氧基）苯基）-5,11-二氢苯并[4,3 - c ]苯二甲基-2,8 -二基-双（2，2-二甲基丙酸酯）（14）。经过三个扩大规模的推广活动后，该11步合成的总产率从0.17％提高到7.1％。
• Benzo \x9bB! indeno \x9b2,1-D! thiophene compounds, intermediates, processes,
  申请人：Eli Lilly and Company

  公开号：US05856341A1

  公开（公告）日：1999-01-05

  The invention provides benzo\x9bb!indenothiophene compounds of formula I ##STR1## wherein, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6, are as defined in the specification, intermediates, formulations, and methods of inhibiting bone loss or bone resorption, particularly osteoporosis, cardiovascular-related pathological conditions including hyperlipidemia and related cardiovascular pathologies, and estrogen-dependent cancer.

  本发明提供了式I的苯并[b]噻吩化合物，其中R.sup.1，R.sup.2，R.sup.3，R.sup.4，R.sup.5和R.sup.6如规范所定义，以及中间体、制剂和抑制骨质流失或骨吸收的方法，特别是骨质疏松症、高脂血症和相关心血管病理条件，以及雌激素依赖性癌症。
• [EN] TETRACYCLIC HETEROCOMPOUNDS AS ESTROGEN RECEPTOR MODULATORS<br/>[FR] HETERO-COMPOSES TETRACYCLIQUES UTILISABLES COMME MODULATEURS DU RECEPTEUR DES OESTROGENES
  申请人：ORTHO MCNEIL PHARM INC

  公开号：WO2003053977A1

  公开（公告）日：2003-07-03

  The present invention is directed to novel heteroatom containing tetracyclic derivatives, pharmaceutical compositions containing them, their use in the treatment and / or prevention of disorders mediated by one or more estrogen receptors and processes for their preparation. The compounds of the invention are useful in the treatment and / or prevention of disorders associated with the depletion of estrogen such as hot flashes, vaginal dryness, osteopenia and osteoporosis; hormone sensitive cancers and hyperplasia of the breast, endometrium, cervix and prostate; endometriosis, uterine fibroids, osteoarthritis and as contraceptive agents, alone or in combination with a progestogen or progestogen antagonist.

  本发明涉及新型含杂原子的四环衍生物、含有它们的药物组合物、它们在治疗和/或预防由一个或多个雌激素受体介导的疾病中的使用以及它们的制备过程。该发明的化合物在治疗和/或预防与雌激素缺乏有关的疾病方面具有用处，例如潮热、阴道干燥、骨质疏松症和骨质疏松症；激素敏感性癌症和乳腺、子宫内膜、子宫颈和前列腺的增生；子宫内膜异位症、子宫肌瘤、骨关节炎以及作为避孕药物，单独使用或与孕激素或孕激素拮抗剂组合使用。