N-butyl 11-bromoundecanamide | 184636-86-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-butyl 11-bromoundecanamide
• 英文别名: n-Butyl-11-bromoundecanamide；11-bromo-N-butylundecanamide
• CAS: 184636-86-0
• 化学式: C₁₅H₃₀BrNO
• 分子量: 320.313
• InChiKey: ZUEDLLAVKDTSHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-butyl 11-bromoundecanamide 在 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-butyl-11-[[(3S)-2-(4-hydroxybenzoyl)-3,4-dihydro-1H-isoquinolin-3-yl]methoxy]undecanamide
  参考文献：
  名称：

  Identification of a series of tetrahydroisoquinoline derivatives as potential therapeutic agents for breast cancer

  摘要：

  A series of tetrahydroisoquinoline-N-phenylamide derivatives were designed, synthesized, and tested for their relative binding affinities, and antagonistic activities against estrogen receptor (ER). Compound If (relative binding affinity, RBA = 5) showed higher binding affinity than tamoxifen (R BA = 1), a potent ER antagonist and currently being used for breast cancer therapy. Compound If also exerted optimal antagonistic activity against ER in reporter and cell proliferation assays. Interestingly, compound Ij, which only has a minor agonistic effect against ER, acted as a progesterone receptor (PR) antagonist and exerted agonistic activity against AP-1 through ER pathway. Our results show that these new compounds can be employed as leading pharmacophore for further development of potent selective ER and/or PR modulators or antagonists. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.002
• 作为产物：
  描述：

  11-溴十一酸 在 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 N-butyl 11-bromoundecanamide
  参考文献：
  名称：

  Replacing −CH₂CH₂– with −CONH– Does Not Significantly Change Rates of Charge Transport through Ag^TS-SAM//Ga₂O₃/EGaIn Junctions

  摘要：

  This paper describes physical-organic studies of charge transport by tunneling through self-assembled monolayers (SAMs), based on systematic variations of the structure of the molecules constituting the SAM. Replacing a -CH2CH2- group with a -CONH- group changes the dipole moment and polarizability of a portion of the molecule and has, in principle, the potential to change the rate of charge transport through the SAM. In practice, this substitution produces no significant change in the rate of charge transport across junctions of the structure Ag-TS-S(CH2)(m)X(CH2)(n)H//Ga2O3/EGaIn (TS = template stripped, X = -CH2CH2- or -CONH-, and EGaIn = eutectic alloy of gallium and indium). Incorporation of the amide group does, however, increase the yields of working (non-shorting) junctions (when compared to n-alkanethiolates of the same length). These results suggest that synthetic schemes that combine a thiol group on one end of a molecule with a group, R, to be tested, on the other (e.g., HS similar to CONH similar to R) using an amide-based coupling provide practical routes to molecules useful in studies of molecular electronics.

  DOI：

  10.1021/ja301778s

文献信息

• Conversion of Alkyl Halides into the Corresponding Alcohols Under Mild Reaction Conditions
  作者：Clare L. Ruddick、Philip Hodge、Mark P. Houghton

  DOI：10.1055/s-1996-4395

  日期：1996.11

  Reaction of primary, cyclopentyl, allyl and arylmethyl halides, but not an acyclic secondary halide or a tertiary halide, in acetone or tetrahydrofuran with the formate form of a commercial anion-exchange resin gave formate esters in good yields. The formates were hydrolysed efficiently to the corresponding alcohols by a brief treatment with hydrochloric acid. Reaction of primary alkyl bromides or iodides, secondary alkyl bromides, cinnamyl and arylmethyl halides in tetrahydropyran or 1,4-dioxane with the bicarbonate form of the same anion-exchange resin gave the corresponding alcohols directly in good yields. This latter reaction can be carried out successfully in the presence of ester or amide groups.

  在乙酮或四氢呋喃中，初级环戊基、烯丙基和芳甲基卤化物，而非无环次级卤化物或三级卤化物，与商业阴离子交换树脂的甲酸盐形式反应，能高效生成甲酸酯，产率良好。这些甲酸盐通过短暂与盐酸处理，可高效水解为相应的醇。在四氢吡喃或1,4-二恶烷中，初级烷基溴化物或碘化物、次级烷基溴化物、肉桂基和芳甲基卤化物与同种阴离子交换树脂的碳酸氢盐形式反应，可直接生成相应醇，产率良好。后一反应在存在酯或酰胺基团的情况下也能成功进行。
• [EN] COMPOUNDS HAVING ANTIESTROGENIC AND TISSUE SELECTIVE ESTROGENIC PROPERTIES<br/>[FR] COMPOSES AUX PROPRIETES ANTI-OESTROGENES ET OESTROGENES A SELECTIVITE TISSULAIRE
  申请人：UNIV VIRGINIA COMMONWEALTH

  公开号：WO2005016889A1

  公开（公告）日：2005-02-24

  Compounds for the treatment of estrogen-receptor related maladies are provided. In particular, the invention provides compounds that are tetrahydroquinoline phenylamide derivatives and are useful for the treatment of breast and prostate cancer, and osteoporosis.

  提供用于治疗雌激素受体相关疾病的化合物。特别地，本发明提供四氢喹啉苯酰胺衍生物化合物，用于治疗乳腺癌、前列腺癌和骨质疏松症。
• Compounds having antiestrogenic and tissue selective estrogenic properties, and compounds with anti-androgenic properties for treatment of prostate cancer and androgen receptor dependent diseases
  申请人：Danso-Danquah Richmond

  公开号：US20060287359A1

  公开（公告）日：2006-12-21

  Compounds for the treatment of estrogen-receptor related maladies are provided. Compounds with anti-androgenic properties also are provided. In particular, the invention provides compounds that are tetrahydroquinoline phenylamide derivatives and are useful for the treatment of breast and prostate cancer, and osteoporosis.

  提供用于治疗雌激素受体相关疾病的化合物。还提供具有抗雄激素特性的化合物。具体地，本发明提供了四氢喹啉苯酰胺衍生物化合物，可用于治疗乳腺癌、前列腺癌和骨质疏松症。
• Staudinger; Joerder, Journal fur praktische Chemie (Leipzig 1954), 1942, vol. <2>160, p. 175
  作者：Staudinger、Joerder

  DOI：——

  日期：——
• US7601739B2
  申请人：——

  公开号：US7601739B2

  公开（公告）日：2009-10-13