5-(1-iodopentyl)-β-naphthol | 940281-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(1-iodopentyl)-β-naphthol
• 英文别名: 2-((5-iodopentyl)oxy)naphthalene；2-(5-Iodopentoxy)naphthalene；2-(5-iodopentoxy)naphthalene
• CAS: 940281-79-8
• 化学式: C₁₅H₁₇IO
• 分子量: 340.204
• InChiKey: VOAYXFQLBPSNDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(1-iodopentyl)-β-naphthol 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 125.0h， 生成
  参考文献：
  名称：

  Synthesis of carbamate derivatives of iejimalides. Retention of normal antiproliferative activity and localization of binding in cancer cells

  摘要：

  The syntheses of six iejimalide carbamate derivatives are described. Their biological activity and those of the unmodified iejimalides A and B against breast and prostate cancer cell lines were determined. These results show that the serine hydroxyl group of iejimalides A and B is a permissive site that can be functionalized to form carbamate derivatives without significant loss of normal biological activity. This method of derivatization will be valuable for cellular target identification, mechanism of action studies, and drug development efforts. A fluorescent derivative does not exhibit binding to the cytoskeletal features of cancer cells. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.046
• 作为产物：
  描述：

  1,5-二碘戊烷 、 2-萘酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 27.0h， 以89%的产率得到5-(1-iodopentyl)-β-naphthol
  参考文献：
  名称：

  Synthesis of carbamate derivatives of iejimalides. Retention of normal antiproliferative activity and localization of binding in cancer cells

  摘要：

  The syntheses of six iejimalide carbamate derivatives are described. Their biological activity and those of the unmodified iejimalides A and B against breast and prostate cancer cell lines were determined. These results show that the serine hydroxyl group of iejimalides A and B is a permissive site that can be functionalized to form carbamate derivatives without significant loss of normal biological activity. This method of derivatization will be valuable for cellular target identification, mechanism of action studies, and drug development efforts. A fluorescent derivative does not exhibit binding to the cytoskeletal features of cancer cells. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.046

文献信息

• Copper-Catalyzed/Promoted Cross-coupling of <i>gem</i>-Diborylalkanes with Nonactivated Primary Alkyl Halides: An Alternative Route to Alkylboronic Esters
  作者：Zhen-Qi Zhang、Chu-Ting Yang、Lu-Jun Liang、Bin Xiao、Xi Lu、Jing-Hui Liu、Yan-Yan Sun、Todd B. Marder、Yao Fu

  DOI：10.1021/ol503111h

  日期：2014.12.19

  The first copper-catalyzed/promoted sp(3)-C SuzukiMiyaura coupling reaction of gem-diborylalkanes with nonactivated electrophilic reagents is reported. Not only 1, 1-diborylalkanes but also some other gem-diborylalkanes can be coupled with nonactivated primary alkyl halides, offering a new method for sp(3)Csp(3)C bond formation and, simultaneously, providing a new strategy for the synthesis of alkylboronic esters.