1-溴-2-十四烷醇 | 10567-14-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 中文名称: 1-溴-2-十四烷醇
• 英文名称: 1-bromo-2-tetradecanol
• 英文别名: 1-bromo-tetradecan-2-ol
• CAS: 10567-14-3
• 化学式: C₁₄H₂₉BrO
• 分子量: 293.288
• InChiKey: RZXGLMPZNPLHJN-UHFFFAOYSA-N

物化性质

• 沸点：
  347.7±15.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  16.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-溴-2-十四烷醇 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以100%的产率得到1-溴十四烷-2-酮
  参考文献：
  名称：

  Niphatenones, Glycerol Ethers from the Sponge Niphates digitalis Block Androgen Receptor Transcriptional Activity in Prostate Cancer Cells: Structure Elucidation, Synthesis, and Biological Activity

  摘要：

  Extracts of the marine sponge Niphates digitalis collected in Dominica showed strong activity in a cell-based assay designed to detect antagonists of the androgen receptor (AR) that could act as lead compounds for the development of a new class of drugs to treat castration recurrent prostate cancer (CRPC). Assay-guided fractionation showed that niphatenones A (3) and B (4), two new glycerol ether lipids, were the active components of the extracts. The structures of 3 and 4 were elucidated by analysis of NMR and MS data and confimed via total synthesis. Biological evaluation of synthetic analogues of the niphatenones has shown that the enantiomers 7 and 8 are more potent than the natural products in the screening assay and defined preliminary SAR for the new AR antagonist pharmacophore, including the finding that the Michael acceptor enone functionality is not required for activity. Niphatenone B (4) and its enantiomer 8 blocked androgen-induced proliferation of LNCaP prostate cancer cells but had no effect on the proliferation of PC3 prostate cancer cells that do not express functional AR, consistent with activity as AR antagonists. Use of the propargyl ether 44 and Click chemistry showed that niphatenone B binds covalently to the activation function-1 (AF1) region of the AR N-terminus domain (NTD).

  DOI：

  10.1021/jm2014056
• 作为产物：
  描述：

  1-十四烯 在 N-溴代丁二酰亚胺(NBS) 、 三氯化铁 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1-溴-2-十四烷醇
  参考文献：
  名称：

  Acylcarnitine analogues as topical, microbicidal spermicides.

  摘要：

  Acylcarnitine analogues, (+)-6-Carboxylatomethyl-2-alkyl-4,4-dimethylmorpholinium (Z-n, where n = the number of carbons in the alkyl chain), synthesized in multi-gram quantities show in vitro activities as spermicides, anti-HIV agents, and inhibitors of the growth of Candida albicans. Activity improves with increasing chain length. Compound Z-15 is a candidate for further study as a topical, microbicidal spermicide. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00423-0

文献信息

• Spermicidal, anti-HIV, and micellar properties of di- and trihydroxylated cationic surfactants
  作者：Yue-Ling Wong、Christopher L Curfman、Gustavo F Doncel、M Patricia Hubieki、Travis C Dudding、Prashant S Savle、Richard D Gandour

  DOI：10.1016/s0040-4020(01)01114-0

  日期：2002.1

  effective at 0.1 mg mL−1 in the cell-free assay and 0.5 mg mL−1 in the cell-associated assay. Compound 1(16) shows the best combination of dual activity against sperm and HIV. In summary, hydroxylated cationic surfactants, 1 and 2, show promise as inexpensive topical, contraceptive microbicides.

  2-羟基-N-（2-羟乙基）-N，N-二甲基-1-烷胺1（p）和2-羟基-N，N-双（2-羟乙基）-N-甲基-1- alkanaminium 2（p为同源系列中描述）溴化物，tetradECanaminium（p = 14）通过octadECaminium（p= 18）。该系列偶数成员的临界胶束浓度（cmc's）在25和37°C下通过电导率测量，显示了预期的线性依赖于链长。所有化合物均显示杀精和杀虫活性。在Sander–Cramer杀虫剂测定法1和2中，最小有效浓度（MEC）与链长的关系图分别显示了截止效应和抛物线关系。最好的化合物1（17）和1（18）的MEC（〜0.12 mg mL -1）略低于市售杀精子剂壬氧化酚9（N-9）。化合物1（16）和2（17）在体外，无细胞和细胞相关的病毒灭活试验中显示出最佳的抗HIV活性。两者在无细胞测定中均为0.1 mg mL -1，在细胞相关测定中均为0
• Facile one-pot synthesis of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent
  作者：Rajendra D. Patil、Girdhar Joshi、Subbarayappa Adimurthy、Brindaban C. Ranu

  DOI：10.1016/j.tetlet.2009.03.047

  日期：2009.5

  A new method for the preparation of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent has been developed. Several α-bromoketones were successfully prepared from a variety of olefins by this method. This procedure is an alternative to conventional molecular bromine.

  已开发出一种使用溴化物/溴酸盐对作为无害溴化剂，由烯烃制备α-溴代酮的新方法。通过这种方法成功地由多种烯烃制备了几种α-溴代酮。该方法是常规分子溴的替代方法。
• Cobalt-Mediated Mizoroki-Heck-Type Reaction of Epoxide with Styrene
  作者：Yousuke Ikeda、Hideki Yorimitsu、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1002/adsc.200404074

  日期：2004.12

  Treatment of a mixture of epoxide and styrene with trimethylsilylmethylmagnesium bromide in the presence of a cobalt-phosphine complex afforded homocinnamyl alcohol in good yield. The reaction should begin with ring opening of the epoxide by the action of magnesium bromide which leads to the formation of a magnesium 2-bromoethoxide derivative and not with a direct single electron transfer from a cobalt

  在钴-膦配合物的存在下用三甲基甲硅烷基甲基溴化镁处理环氧化物和苯乙烯的混合物，以高收率得到高肉桂醇。该反应应开始于通过溴化镁的作用使环氧化物开环，这导致2-溴乙氧基镁的形成，而不是从钴络合物到环氧化物的直接单电子转移。
• 一种含羟基可电离脂质及其制备方法与应用
  申请人：武汉大学

  公开号：CN117658839A

  公开（公告）日：2024-03-08

  本发明公开了一种含羟基可电离脂质及其制备方法与应用，属于核酸药物载体技术领域。本发明的含羟基可电离脂质的结构式如下所示，其可用于制备脂质体纳米粒子或核酸药物载体。本发明的可电离脂质中侧链羟基的引入，联合头部羟基，可以显著增加可电离脂质与核酸分子的结合能力，提高脂质体纳米颗粒的载药量，显著减少脂质体纳米颗粒制备时总脂质的投入量，降低脂质体纳米颗粒的毒性。#imgabs0#
• Enzymic hydration of [18O]epoxides. Role of nucleophilic mechanisms
  作者：Robert P. Hanzlik、Marshall Edelman、William J. Michaely、Georganna Scott

  DOI：10.1021/ja00423a050

  日期：1976.3