1-bromo-3,4-dimethoxy-2-propylbenzene | 142601-49-8

• 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: 1-bromo-3,4-dimethoxy-2-propylbenzene
• 英文别名: 6-bromo-2,3-dimethoxybenzenepropane；1-bromo-3,4-dimethoxy-2-n-propylbenzene
• CAS: 142601-49-8
• 化学式: C₁₁H₁₅BrO₂
• 分子量: 259.143
• InChiKey: DTNWSLXLUUVFDX-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：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-bromo-3,4-dimethoxy-2-propylbenzene 在 palladium on activated charcoal 氢氧化钾 、 溴乙烷 、 polyphosphoric ester 、 氢气 、 magnesium 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 25.0~60.0 ℃ 、413.69 kPa 条件下， 反应 30.0h， 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

• Synthesis of naphthalene and indene precursors to naphthoic and indenoic acids
  作者：Lorraine M. Deck、Jacob A. Greenberg、Taylor S. Busby、Elizabeth R. Bright、Lisa J. Whalen、David L. Vander Jagt、Robert E. Royer

  DOI：10.1016/j.tetlet.2013.08.067

  日期：2013.11

  As part of ongoing research to investigate structural requirements for lactate dehydrogenase inhibition by highly substituted naphthoic and indenoic acids, certain naphthalene and indene precursors to those types of compounds are required. Described here are efficient preparations of 1-naphthoic acid precursors 6-benzyl-2,3-dimethoxy-1-propylnaphthalenes, including compounds with substituted benzyl

  作为正在进行的研究的一部分，以研究高度取代的萘甲酸和茚满酸抑制乳酸脱氢酶的结构要求，需要这些类型化合物的某些萘和茚前体。这里描述的是1-萘甲酸前体6-苄基-2，3-二甲氧基-1-丙基萘的有效制备方法，包括具有取代的苄基和7-苄基-2，3-二甲氧基-1-丙基萘的化合物。还描述了茚甲酸前体2-苄基-5，6-二甲氧基-7-丙基-1 H-茚的合成，包括具有取代的苄基的化合物。这些化合物由关键中间体6,7-二甲氧基-5-丙基-1-四氢萘酮，6,7-二甲氧基-8-丙基-1-四氢萘酮和5,6-二甲氧基-4-丙基-1-四氢萘酮制成。
• Novel 2-saccharinylmethyl and 4,5,6,7-tetrahydro-2-saccharinylmethyl phosphates, phosphonates and phosphinates useful as proteolytic enzyme inhibitors and compositions and method of use thereof
  申请人：STERLING WINTHROP INC.

  公开号：EP0549073A1

  公开（公告）日：1993-06-30

  Novel 4-R₁-R₂-R₃-2-saccharinylmethyl, 4-R₄-4-R₅-6-R₆-4,5,6,7-tetrahydro-2-saccharinylmethyl and 4,7-C-4,5,6,7-tetrahydro-2-saccharinylmethyl phosphates, phosphonates and phosphinates of formulas I, II and IIA respectively are useful in the treatment of degenerative diseases, and compositions containing them, methods for using them to treat degenerative diseases, and processes for their preparation by reaction of the corresponding 2-halomethylsaccharins with a phosphate, phosphonate or phosphinic acidderivative.

  分别为式 I、II 和 IIA 的新型 4-R₁-R₂-R₃-2-糖精基甲基、4-R₄-4-R₅-6-R₆-4,5,6,7-四氢-2-糖精基甲基和 4,7-C-4,5,6,7-四氢-2-糖精基甲基膦酸盐、膦酸盐和膦酸盐 可用于治疗退行性疾病，以及含有这些物质的组合物、使用这些物质治疗退行性疾病的方法，以及通过相应的 2-半甲基糖与磷酸盐、膦酸盐或膦酸衍生物反应制备这些物质的工艺。
• 2-Saccharinylmethyl heterocyclic carboxylates useful as proteolytic enzyme inhibitors and pharmaceutical compositions containing them
  申请人：STERLING WINTHROP INC.

  公开号：EP0550111A1

  公开（公告）日：1993-07-07

  4-R⁴-R⁵-2-Saccharinylmethyl heterocyclic carboxylates, having the formula: wherein:    Het is a 5- or 6-membered monocyclic heterocycle or a 9- or 10-membered bicyclic heterocycle containing from 1 to 2 heteroatoms selected from oxygen, nitrogen and sulfur or said heterocycles substituted by from one to three, the same or different, members of the group consisting of lower-alkyl, perfluorolower-alkyl, lower-alkoxy, oxo, phenyl, halogen, and -O-(C₂-C₁₀ alkylene)-N=B where N=B is dilower-alkylamino, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 1-piperazinyl, or 4-lower-alkyl-1-piperazinyl;    R⁴ is hydrogen, halogen , lower-alkyl, perfluorolower-alkyl, perchlorolower-alkyl, lower-alkenyl, lower-alkynyl, cyano, carboxamido, amino, lower-alkylamino, dilower-alkylamino, lower-alkoxy, benzyloxy, lower-alkoxycarbonyl, hydroxy or phenyl; and    R⁵ is hydrogen or from one to two substituents in any of the 5-, 6- or 7-positions. The compounds of the present invention inhibit the activity of serine proteases, specifically human leukocyte elastase and the chymotrypsin-like enzymes, and are thus useful in the treatment of degenerative disease conditions such as emohysema, rheumatoid arthritis, pancreatitis, cystic fibrosis, chronic bronchitis, adult respiratory distress syndrome, inflammatory bowel disease, psoriasis, bullous pemphigoid and alpha-1-antitrypsin deficiency.

  4-R⁴-R⁵-2-糖精甲基杂环羧酸盐，其化学式为 其中 Het 是 5 或 6 元单环杂环或 9 或 10 元双环杂环，其中含有 1 至 2 个选自氧、氮和硫的杂原子，或所述杂环被 1 至 3 个相同或不同的杂原子取代、由低级烷基、全氟低级烷基、低级烷氧基、氧代、苯基、卤素和-O-(C₂-C₁₀亚烷基)-N=B 组成的组中的成员，其中 N=B 是稀低级烷基氨基、1-吡咯烷基、1-哌啶基、4-吗啉基、1-哌嗪基或 4-低级烷基-1-哌嗪基； R⁴ 是氢、卤素、低级烷基、全氟低级烷基、全氯低级烷基、低级烯基、低级炔基、氰基、羧酰胺基、氨基、低级烷基氨基、稀释低级烷基氨基、低级烷氧基、苄氧基、低级烷氧基羰基、羟基或苯基；以及 R⁵ 是氢或 5、6 或 7 位上的一至两个取代基。 本发明的化合物可抑制丝氨酸蛋白酶的活性，特别是人白细胞弹性蛋白酶和糜蛋白酶样酶，因此可用于治疗退行性疾病，如肺气肿、类风湿性关节炎、胰腺炎、囊性纤维化、慢性支气管炎、成人呼吸窘迫综合征、炎症性肠病、银屑病、大疱性类天疱疮和α-1-抗胰蛋白酶缺乏症。
• 2-Saccharinylmethyl aryl and aryloxy acetates useful as proteolytic enzyme inhibitors and pharmaceutical compositions contaning them
  申请人：STERLING WINTHROP INC.

  公开号：EP0550112A1

  公开（公告）日：1993-07-07

  4-R⁴-R⁵-2-Saccharinylmethyl aryl and aryloxy acetates, having the formula: wherein: mis zero or one, n is zero or one, and the sum of m + n is zero or one; R1is hydrogen or lower-alkyl; R2is hydrogen or lower-alkyl; R3is phenyl or phenyl substituted by from one to three, the same or different, members of the group consisting of lower-alkyl perfluorolower-alkyl, lower-alkoxy and halogen; R4is hydrogen, halogen, lower-alkyl, perfluorolower-alkyl, perchlorolower-alkyl, lower-alkenyl, lower-alkynyl, cyano, carboxamido, amino, lower-alkylamino, dilower-alkylamino, lower-alkoxy, benzyloxy, lower-alkoxycarbonyl, hydroxy or phenyl; and R5is hydrogen or from one to two substituents in any of the 5-, 6- or 7-positions. The compounds of the present invention inhibit the activity of serine proteases, specifically human leukocyte elastase and the chymotrypsin-like enzymes, and are thus useful in the treatment of degenerative disease conditions such as emphysema, rheumatoid arthritis, pancreatitis, cysticfibrosis, chronic bronchitis, adult respiratory distress syndrome, inflammatory bowel disease, psoriasis, bullous pemphigoid and alpha-1-antitrypsin deficiency.

  4-R⁴-R⁵-2-糖精甲基芳基和芳氧基乙酸酯，其式为 其中 mis为零或一，n为零或一，m+n之和为零或一； R1 是氢或低级烷基； R2 是氢或低级烷基 R3 是苯基或被 1 至 3 个相同或不同的低级烷基全氟低级烷基、低级烷氧基和卤素组成的组中的成员取代的苯基； R4 是氢、卤素、低级烷基、全氟低级烷基、全氯低级烷基、低级烯基、低级炔 基、氰基、羧酰胺基、氨基、低级烷基氨基、稀释低级烷基氨基、低级烷氧基、 苄氧基、低级烷氧基羰基、羟基或苯基；以及 R5 为氢或 5、6 或 7 位上的一至两个取代基。 本发明的化合物可抑制丝氨酸蛋白酶的活性，特别是人白细胞弹性蛋白酶和糜蛋白酶样酶，因此可用于治疗退行性疾病，如肺气肿、类风湿性关节炎、胰腺炎、囊性纤维化、慢性支气管炎、成人呼吸窘迫综合征、炎症性肠病、银屑病、大疱性类天疱疮和α-1-抗胰蛋白酶缺乏症。
• Synthesis of hemigossypol and its derivatives
  作者：Jun Wei、David L. Vander Jagt、Robert E. Royer、Lorraine M. Deck

  DOI：10.1016/j.tetlet.2010.08.089

  日期：2010.11

  Hemigossypol (3), a sesquiterpene natural product, was previously isolated from Gossypium barbadense and was shown to display improved anti-furgal activity compared to gossypol (1), the disesquiterpene chiller of hemigossypol (3). Gossypol exhibits multiple biological activities. In order to study whether hemigossypol and its derivatives retain the various bioactivities of gossypol, we developed a short and convenient synthetic scheme to synthesize hemigossypol. This is the first de novo synthesis of this natural product. In addition derivatives of hemigossypol with various 2,5-alkyl substituents were synthesized. Modification of the synthetic scheme also afforded the natural product hemigossylic lactone (4) and its 2,5-substituted derivatives. (C) 2010 Elsevier Ltd. All rights reserved.