1,2,3,4-tetrahydro-5-methoxy-2,2-dimethylnaphthalene | 199442-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2,3,4-tetrahydro-5-methoxy-2,2-dimethylnaphthalene
• 英文别名: 8-methoxy-3,3-dimethyl-2,4-dihydro-1H-naphthalene
• CAS: 199442-38-1
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: JHQBMYKTRVDXNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  1,2,3,4-tetrahydro-5-methoxy-2,2-dimethylnaphthalene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以98%的产率得到5,6,7,8-tetrahydro-6,6-dimethyl-1-naphthol
  参考文献：
  名称：

  Anti-AIDS agents 72. Bioisosteres (7-carbon-DCKs) of the potent anti-HIV lead DCK

  摘要：

  Three 9, 10-di- O-(-)-camphanoyl-7,8,9, 10-tetrahyd to -benzo [h]chromen-2- one (7-carbon-DCK) analogs (3a-C) were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. All three new carbon bioisosteres of the anti-HIV lead DCK showed anti-HIV activity. Compound 3a had an EC50 value of 0.068 pM, which was comparable to that of DCK in the same assay. The preliminary results indicated that 7-carbon-DCK analogs merit attention as potential HIV-1 inhibitors for further development into clinical trials candidates. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.026
• 作为产物：
  描述：

  7-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one 在 三乙基硅烷 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 氯化锆(IV) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.5h， 生成 1,2,3,4-tetrahydro-5-methoxy-2,2-dimethylnaphthalene
  参考文献：
  名称：

  滑动环己烷重排

  摘要：

  可以通过四氯化锆的作用将6-甲氧基四氢化萘转化为8-甲氧基四氢化萘。尽管周转缓慢，但产量总体上还是不错的。超声辐射，相转移催化剂，冠醚和氯化锂都可加速反应，该反应通过C-1至C-8a键的断裂和分子内Friedel-Crafts烷基化环化而进行。

  DOI：

  10.1016/s0040-4020(97)10014-x

文献信息

• Anti-AIDS agents 72. Bioisosteres (7-carbon-DCKs) of the potent anti-HIV lead DCK
  作者：Yang Wang、Shao-Xu Huang、Peng Xia、Yi Xia、Zheng-Yu Yang、Nicole Kilgore、Susan L. Morris-Natschke、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2007.05.026

  日期：2007.8

  Three 9, 10-di- O-(-)-camphanoyl-7,8,9, 10-tetrahyd to -benzo [h]chromen-2- one (7-carbon-DCK) analogs (3a-C) were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. All three new carbon bioisosteres of the anti-HIV lead DCK showed anti-HIV activity. Compound 3a had an EC50 value of 0.068 pM, which was comparable to that of DCK in the same assay. The preliminary results indicated that 7-carbon-DCK analogs merit attention as potential HIV-1 inhibitors for further development into clinical trials candidates. (c) 2007 Elsevier Ltd. All rights reserved.
• The sliding cyclohexane rearrangement
  作者：David C Harrowven、Richard F Dainty

  DOI：10.1016/s0040-4020(97)10014-x

  日期：1997.11

  transformed into 8-methoxytetralins through the action of zirconium tetrachloride. Yields are generally good though turnover is slow. Ultrasonic irradiation, phase transfer catalysts, crown ethers and lithium chloride all accelerate the reaction which proceeds via scission of the C-1 to C-8a bond and cyclisation by intramolecular Friedel-Crafts alkylation.

  可以通过四氯化锆的作用将6-甲氧基四氢化萘转化为8-甲氧基四氢化萘。尽管周转缓慢，但产量总体上还是不错的。超声辐射，相转移催化剂，冠醚和氯化锂都可加速反应，该反应通过C-1至C-8a键的断裂和分子内Friedel-Crafts烷基化环化而进行。