3,4-dihydro-6,7-dimethoxy-3-methyl-5-n-propyl-1(2H)naphthalenone | 213971-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3,4-dihydro-6,7-dimethoxy-3-methyl-5-n-propyl-1(2H)naphthalenone
• 英文别名: 6,7-Dimethoxy-3-methyl-5-propyl-3,4-dihydronaphthalen-1(2H)-one；6,7-dimethoxy-3-methyl-5-propyl-3,4-dihydro-2H-naphthalen-1-one
• CAS: 213971-37-0
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: GOFHNNSCJZKORF-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C
• 沸点：
  398.2±42.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-6,7-dimethoxy-3-methyl-5-n-propyl-1(2H)naphthalenone 生成 2,3-Dimethoxy-7-methyl-1-n-propylnaphthalene
  参考文献：
  名称：

  Hydroxynaphthoic acids and derivatives

  摘要：

  在一种实施方式中，本发明提供一种化合物，其包括：##STR1## 其中A=H或OH，X=OH，卤素，OR，NHR，NR'R"，其中R，R'和R"=H，C.sub.1-8烷基，C.sub.2-8烯基，或C.sub.2-8炔基，环烷基，环烯基，芳基，芳基烷基或杂环烷基，取代或未取代；以及R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5=H，C.sub.1-8烷基，C.sub.2-8烯基，或C.sub.2-8炔基，环烷基，环烯基，芳基或杂环烷基，取代或未取代，其中R.sub.1至少包括一个亚甲基间隔，通过该亚甲基间隔R.sub.1连接到所述化合物。本发明还提供制备羟基萘甲酸的方法。

  公开号：

  US06124498A1
• 作为产物：
  描述：

  (E)-4-(3,4-Dimethoxy-2-propyl-phenyl)-4-hydroxy-3-methyl-but-2-enoic acid 在 palladium on activated charcoal polyphosphoric ester 、 氢气 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 60.0 ℃ 、413.69 kPa 条件下， 反应 25.0h， 生成 3,4-dihydro-6,7-dimethoxy-3-methyl-5-n-propyl-1(2H)naphthalenone
  参考文献：
  名称：

  Selective Inhibitors of Human Lactate Dehydrogenases and Lactate Dehydrogenase from the Malarial Parasite Plasmodium falciparum

  摘要：

  Derivatives of the sesquiterpene 8-deoxyhemigossylic acid (2,3-dihydroxy-6-methyl-4-(1-methylethyl)-1-naphthoic acid) were synthesized that contained altered alkyl groups in the 4-position and contained alkyl or aralkyl groups in the 7-position. These substituted dihydroxynaphthoic acids are selective inhibitors of human lactate dehydrogenase-H (LDHH) and LDH-M and of lactate dehydrogenase from the malarial parasite Plasmodium falciparum (pLDH). All inhibitors are competitive with the binding of NADH. Selectivity for LDH-H, LDH-M, or pLDH is strongly dependent upon the groups that are in the 4- and 7-positions of the dihydroxynaphthoic acid backbone. Dissociation constants as low as 50 nM were observed, with selectivity as high as 400-fold.

  DOI：

  10.1021/jm980334n

文献信息

• Hydroxynaphthoic acids and derivatives
  申请人：University Of New Mexico

  公开号：US06124498A1

  公开（公告）日：2000-09-26

  In one embodiment, the present invention provides a compound comprising: ##STR1## wherein A=H or OH X=OH, a halogen, OR, NHR, NR'R" where R, R', and R"=H, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, or C.sub.2-8 alkynyl, cycloalkyl, cycloalkenyl, aryl, aralkyl or heterocyclic, substituted or unsubstituted; and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 =H, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, or C.sub.2-8 alkynyl, cycloalkyl, cyloalkenyl, aryl or heterocyclic, substituted or unsubstituted, wherein R.sub.1 includes at least one methylene spacer through which R.sub.1 is attached to said compound. The present invention also provides methods for making hydroxynaphthoic acids.

  在一种实施方式中，本发明提供一种化合物，其包括：##STR1## 其中A=H或OH，X=OH，卤素，OR，NHR，NR'R"，其中R，R'和R"=H，C.sub.1-8烷基，C.sub.2-8烯基，或C.sub.2-8炔基，环烷基，环烯基，芳基，芳基烷基或杂环烷基，取代或未取代；以及R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5=H，C.sub.1-8烷基，C.sub.2-8烯基，或C.sub.2-8炔基，环烷基，环烯基，芳基或杂环烷基，取代或未取代，其中R.sub.1至少包括一个亚甲基间隔，通过该亚甲基间隔R.sub.1连接到所述化合物。本发明还提供制备羟基萘甲酸的方法。
• Synthesis of benzyl substituted naphthalenes from benzylidene tetralones
  作者：Lorraine M. Deck、Quintino Mgani、Andrea Martinez、Alice Martinic、Lisa J. Whalen、David L. Vander Jagt、Robert E. Royer

  DOI：10.1016/j.tetlet.2011.11.065

  日期：2012.1

  tetralones provided 1-substituted benzyl naphthalenes. The reported synthesis is flexible and scalable and provides access to naphthalenes having a variety of substitution patterns. These benzyl substituted naphthalenes are being converted to naphthoic acids and the bioactivities of these compounds are currently being investigated.

  描述了一种新型的高度取代的二甲氧基苄基萘的方便和有效的合成，它是几种二羟基萘甲酸的前体。该方法涉及使用羟醛化学来提供许多亚苄基四氢萘酮，它们在三个步骤中被转化为目标萘，收率非常好。中间体苄基四氢萘的格氏反应提供了 1-取代的苄基萘。报道的合成是灵活和可扩展的，并提供了获得具有多种取代模式的萘的途径。这些苄基取代的萘正在转化为萘甲酸，目前正在研究这些化合物的生物活性。
• Synthesis of Naphthoic Acids as Potential Anticancer Agents
  作者：Lorraine Deck、Jacob Greenberg、Lisa Whalen、David Vander Jagt、Robert Royer

  DOI：10.1055/s-0037-1611342

  日期：2019.1

  As part of ongoing research to investigate structural requirements for lactate dehydrogenase inhibition by highly substituted naphthoic acids, nine new aryl-substituted dihydroxynaphthoic acids were synthesized from three known precursors. Described here are efficient preparations of the 1-naphthoic acid target compounds by using Suzuki coupling reactions, formylations, oxidations, and demethylations

  作为研究高度取代的萘甲酸对乳酸脱氢酶抑制的结构要求的持续研究的一部分，从三种已知的前体合成了九种新的芳基取代的二羟基萘甲酸。这里描述的是通过使用 Suzuki 偶联反应、甲酰化、氧化和去甲基化有效制备 1-萘甲酸目标化合物。用五种化合物进行的乳酸脱氢酶抑制研究揭示了低微摩尔范围内的抑制常数 K i 值。
• US6124498A
  申请人：——

  公开号：US6124498A

  公开（公告）日：2000-09-26
• Selective Inhibitors of Human Lactate Dehydrogenases and Lactate Dehydrogenase from the Malarial Parasite <i>Plasmodium</i> <i>f</i><i>alciparum</i>
  作者：Lorraine M. Deck、Robert E. Royer、Brian B. Chamblee、Valerie M. Hernandez、Richard R. Malone、Jose E. Torres、Lucy A. Hunsaker、Robert C. Piper、Michael T. Makler、David L. Vander Jagt

  DOI：10.1021/jm980334n

  日期：1998.9.1

  Derivatives of the sesquiterpene 8-deoxyhemigossylic acid (2,3-dihydroxy-6-methyl-4-(1-methylethyl)-1-naphthoic acid) were synthesized that contained altered alkyl groups in the 4-position and contained alkyl or aralkyl groups in the 7-position. These substituted dihydroxynaphthoic acids are selective inhibitors of human lactate dehydrogenase-H (LDHH) and LDH-M and of lactate dehydrogenase from the malarial parasite Plasmodium falciparum (pLDH). All inhibitors are competitive with the binding of NADH. Selectivity for LDH-H, LDH-M, or pLDH is strongly dependent upon the groups that are in the 4- and 7-positions of the dihydroxynaphthoic acid backbone. Dissociation constants as low as 50 nM were observed, with selectivity as high as 400-fold.