2-benzyloxy-6-bromo-3-methoxybenzyl alcohol | 590361-96-9

• 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: 2-benzyloxy-6-bromo-3-methoxybenzyl alcohol
• 英文别名: (2-Benzyloxy-6-bromo-3-methoxy-phenyl)-methanol；(6-bromo-3-methoxy-2-phenylmethoxyphenyl)methanol
• CAS: 590361-96-9
• 化学式: C₁₅H₁₅BrO₃
• 分子量: 323.186
• InChiKey: AODKIFCCBASXCD-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C
• 沸点：
  425.2±40.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzyloxy-6-bromo-3-methoxybenzyl alcohol 在 咪唑 、 四丁基氟化铵 、 叔丁基锂 、 sodium hydride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 44.5h， 生成 1-[2-Benzyloxy-6-(3-isopropenyl-1-methoxy-4-methyl-pent-3-enyl)-3-methoxy-phenyl]-propenone
  参考文献：
  名称：

  A stereoselective intramolecular Diels–Alder strategy for the tricyclo[9.3.1.03,8]pentadecane core of aromatic C-ring taxanes

  摘要：

  A stereoselective Lewis acid-catalyzed and chelation controlled intramolecular Diels-Alder entry into the tricyclo[9.3.1.0(3,8)]pentadecane core of aromatic C-ring taxanes is described. The approach affords an efficient, high yield, access to aromatic C-ring taxanes variably functionalized at the C2, C4, C5, and C9 positions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01120-1
• 作为产物：
  描述：

  邻香草醛 在 4-二甲氨基吡啶 sodium tetrahydroborate 、 溴 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 、 potassium bromide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 2-benzyloxy-6-bromo-3-methoxybenzyl alcohol
  参考文献：
  名称：

  A stereoselective intramolecular Diels–Alder strategy for the tricyclo[9.3.1.03,8]pentadecane core of aromatic C-ring taxanes

  摘要：

  A stereoselective Lewis acid-catalyzed and chelation controlled intramolecular Diels-Alder entry into the tricyclo[9.3.1.0(3,8)]pentadecane core of aromatic C-ring taxanes is described. The approach affords an efficient, high yield, access to aromatic C-ring taxanes variably functionalized at the C2, C4, C5, and C9 positions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01120-1

文献信息

• An efficient synthesis of 4-isochromanones via Parham-type cyclization with Weinreb amide
  作者：Chaolei Wang、Zheng Wu、Jia Wang、Jie Liu、Hequan Yao、Aijun Lin、Jinyi Xu

  DOI：10.1016/j.tet.2015.08.028

  日期：2015.10

  The synthesis of 4-isochromanones via Parham-type cyclization with Weinreb amide as the internal electrophilic group, t-BuLi as the lithium reagent was described. The reaction was efficient and could be completed in one minute. The application scope of this new protocol was investigated and the desired products could be obtained in good to excellent yields. Besides, the synthetic potential of this

  4-异色满酮类经由帕海姆型环化的Weinreb合成酰胺作为内部电子基团，吨正丁基锂作为被描述的锂试剂。该反应是有效的，并且可以在一分钟内完成。这个新的协议的应用范围进行了研究和所需产物可以以良好地获得优异的产率。此外，该方法的合成潜力还通过天然产物（±）-XJP的合成得到了进一步证明，该合成是通过六个步骤获得的，总收率高达54％。
• Total Synthesis and the Biological Activities of (±)-Norannuradhapurine
  作者：Surachai Nimgirawath、Rujee Lorpitthaya、Asawin Wanbanjob、Thongchai Taechowisan、Yue-Mao Shen

  DOI：10.3390/molecules14010089

  日期：——

  The structure previously assigned to the phenolic noraporphine alkaloid, (-)-norannuradhapurine has been confirmed by a total synthesis of the racemic alkaloid in which the key step involved the formation of the C ring by a radical-initiated cyclization. although inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028, (±)-norannuradhapurine inhibits the production of NO, PGE2, TNF-a, IL-1b and IL-6 and the expression of iNOS and COX-2 in RAW 264.7 macrophages stimulated with LPS in vitro.

  先前分配给酚类去甲鸦片碱（-）-去甲安那度拉呋啶的结构已经通过外消旋生物碱的全合成得到证实，其中关键步骤是通过自由基引发环化反应形成C环。尽管对金黄色葡萄球菌ATCC25932、大肠杆菌ATCC10536和白色念珠菌ATCC90028无效，但（±）-去甲安那度拉呋啶抑制了NO、PGE2
• Discovery of Novel 4-Arylisochromenes as Anticancer Agents Inhibiting Tubulin Polymerization
  作者：Wenlong Li、Wen Shuai、Feijie Xu、Honghao Sun、Shengtao Xu、Hong Yao、Jie Liu、Hequan Yao、Zheying Zhu、Jinyi Xu

  DOI：10.1021/acsmedchemlett.8b00217

  日期：2018.10.11

  XJP-L (8), a derivative of the natural product (+/-)-7,8-dihydroxy-3-methylisochroman-4-one isolated from the peel of Musa sapien turn L., was found to exhibit weak inhibitory activity of tubulin polymerization (IC50 = 10.6 mu M) in our previous studies. Thus, a series of 4-arylisochromene derivatives were prepared by incorporating the trimethoxyphenyl moiety into 8, among which compound (+/-)-19b was identified as the most potent compound with IC50 values ranging from 10 to 25 nM against a panel of cancer cell lines. Further mechanism studies demonstrated that (+/-)-19b disrupted the intracellular microtubule network, caused G2/M phase arrest, induced cell apoptosis, and depolarized mitochondria of K562 cells. Moreover, ()-19b exhibited potent in vitro antivascular and in vivo antitumor activities. Notably, the R-configured enantiomer of (+/-)-19b, which was prepared by chiral separation, was slightly more potent than (+/-)-19b and was much more potent than the S-configured enantiomer in both antiproliferative and antitubulin assays. Our findings suggest that (+/-)-19b deserves further research as a potential antitubulin agent for the treatment of cancers.