6,6',7,7'-tetramethoxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-2,2'-binaphthalene | 168787-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,6',7,7'-tetramethoxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-2,2'-binaphthalene
• 英文别名: 5,5'-diisopropyl-6,6',7,7'-tetramethoxy-3,3'-dimethyl-[2,2'-binaphthalene]；6-(6,7-Dimethoxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3-dimethoxy-7-methyl-1-propan-2-ylnaphthalene
• CAS: 168787-78-8
• 化学式: C₃₂H₃₈O₄
• 分子量: 486.651
• InChiKey: JZMDYMUEOKQWPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,6',7,7'-tetramethoxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-2,2'-binaphthalene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以99%的产率得到5,5’-diisopropyl-3,3’-dimethyl-[2,2’-binaphthalene]-6,6’,7,7’-tetraol
  参考文献：
  名称：

  1,1’-去氧棉酚的合成方法

  摘要：

  本发明公开了1,1'‑去氧棉酚的合成方法。该方法包括以下步骤：1、以醋酸棉酚I为起始原料，以醋酸棉酚I为起始原料，脱去醛基得到阿扑棉酚II；2、将阿扑棉酚II乙酰化得到阿扑棉酚III；3、选择性脱去阿扑棉酚III的乙酰基得到中间体IV；4、保护中间体IV的酚羟基得到中间体V；5、将中间体V脱去乙酰基得到中间体VI；6、保护中间体VI的酚羟基得到中间体VII；7、还原中间体的VII被保护的酚羟基得到到1,1'‑去氧棉酚前体VIII；8、脱除1,1'‑去氧棉酚前体VIII的甲氧基得到目标产物1,1'‑去氧棉酚IX。本发明反应原料廉价易得，合成工艺步骤少，且总产率高达45％，反应条件温和，安全性高。本发明工艺过程及后处理简单，易于操作，工业化前景好。

  公开号：

  CN112679319B
• 作为产物：
  描述：

  6-bromo-2,3-dimethoxy-7-methyl-1-(1-methylethyl)naphthalene 在 正丁基锂 、 溴苯 作用下， 生成 6,6',7,7'-tetramethoxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-2,2'-binaphthalene
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of 1,1'-Dideoxygossypol and Related Compounds

  摘要：

  1,1'-Dideoxygossypol (DDG), 1,1'-dideoxygossylic acid (DDGA), 8-deoxyhemigossypol (DHG), and 8-deoxyhemigossylic acid (DHGA) were synthesized and tested for their ability to inhibit the replication of HIV in vitro. The EC(50) for DDGA was <1 mu M, and its threshold cytotoxicity was approximately 20 mu M. DDG was less effective than DDGA against HIV and showed considerable toxicity at 5 mu M. DHGA was ineffective against HN and had very low cytotoxicity. DHG showed some anti-HIV activity, but the threshold cytotoxicity was 5 mu M. The dissociation constants for the binding of the four compounds to human serum albumin were determined by fluorescence quenching titrations, and all four were found to have much lower affinities for albumin than the parent compound gossypol.

  DOI：

  10.1021/jm00013a018

文献信息

• US5780675A
  申请人：——

  公开号：US5780675A

  公开（公告）日：1998-07-14
• US5936120A
  申请人：——

  公开号：US5936120A

  公开（公告）日：1999-08-10
• 1,1’-去氧棉酚的合成方法
  申请人：江苏度未生物工程科技有限公司

  公开号：CN112679319B

  公开（公告）日：2022-05-03

  本发明公开了1,1'‑去氧棉酚的合成方法。该方法包括以下步骤：1、以醋酸棉酚I为起始原料，以醋酸棉酚I为起始原料，脱去醛基得到阿扑棉酚II；2、将阿扑棉酚II乙酰化得到阿扑棉酚III；3、选择性脱去阿扑棉酚III的乙酰基得到中间体IV；4、保护中间体IV的酚羟基得到中间体V；5、将中间体V脱去乙酰基得到中间体VI；6、保护中间体VI的酚羟基得到中间体VII；7、还原中间体的VII被保护的酚羟基得到到1,1'‑去氧棉酚前体VIII；8、脱除1,1'‑去氧棉酚前体VIII的甲氧基得到目标产物1,1'‑去氧棉酚IX。本发明反应原料廉价易得，合成工艺步骤少，且总产率高达45％，反应条件温和，安全性高。本发明工艺过程及后处理简单，易于操作，工业化前景好。
• Synthesis and Anti-HIV Activity of 1,1'-Dideoxygossypol and Related Compounds
  作者：Robert E. Royer、Lorraine M. Deck、Timothy J. Vander Jagt、Francella J. Martinez、Ray G. Mills、Stephen A. Young、David L. Vander Jagt

  DOI：10.1021/jm00013a018

  日期：1995.6

  1,1'-Dideoxygossypol (DDG), 1,1'-dideoxygossylic acid (DDGA), 8-deoxyhemigossypol (DHG), and 8-deoxyhemigossylic acid (DHGA) were synthesized and tested for their ability to inhibit the replication of HIV in vitro. The EC(50) for DDGA was <1 mu M, and its threshold cytotoxicity was approximately 20 mu M. DDG was less effective than DDGA against HIV and showed considerable toxicity at 5 mu M. DHGA was ineffective against HN and had very low cytotoxicity. DHG showed some anti-HIV activity, but the threshold cytotoxicity was 5 mu M. The dissociation constants for the binding of the four compounds to human serum albumin were determined by fluorescence quenching titrations, and all four were found to have much lower affinities for albumin than the parent compound gossypol.