3,4-dibenzyloxyphenylacetyl chloride | 78178-56-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,4-dibenzyloxyphenylacetyl chloride
• 英文别名: 2-[3,4-Bis(phenylmethoxy)phenyl]acetyl chloride
• CAS: 78178-56-0
• 化学式: C₂₂H₁₉ClO₃
• 分子量: 366.844
• InChiKey: SRDYQFMSZNVVMU-UHFFFAOYSA-N

物化性质

• 沸点：
  507.7±50.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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-dibenzyloxyphenylacetyl chloride 在 sodium tetrahydroborate 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 氯仿 、 水 、 乙腈 为溶剂， 反应 18.5h， 生成 O,O',O''-Tribenzyl-6-O-methylnorlaudanosoline
  参考文献：
  名称：

  Stadler, Richard; Zenk, Meinhart H., Liebigs Annalen der Chemie, 1990, # 6, p. 555 - 562

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二苄氧基苯甲醛 在 sodium tetrahydroborate 、 氯化亚砜 、 草酰氯 、 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 3,4-dibenzyloxyphenylacetyl chloride
  参考文献：
  名称：

  设计新的类似物以简化细胞毒性Lamellarin天然产物的结构

  摘要：

  尽管海洋来源的lamellarin天然产物具有治疗潜力，但其亲脂性质阻碍了它们的临床前开发，导致水溶性很差。为了开发更多类似药物的类似物，本研究从细胞毒性活性和亲脂性的角度简化了它们的结构。首先，成功设计了一条改良的总合成路线来构建59个系统设计的lamellarin类似物的文库，然后对其进行细胞毒性和log P测定。连同先前在我们实验室中合成的25种第一代薄片蛋白，对结构-活性和结构-亲脂性之间的关系进行了广泛的评估。我们的结果清楚地表明了层状蛋白骨架周围的其他结构要求，

  DOI：

  10.1002/asia.201403361

文献信息

• Biosynthesis. Part 24. Speculative incorporation experiments with 1-benzylisoquinolines and a logical approach via C₆–C₂and C₆–C₃precursors to the biosynthesis of hasubanonine and protostephanine
  作者：Alan R. Battersby、Raymond C. F. Jones、Rymantas Kazlauskas、Craig W. Thornber、Somsak Ruchirawat、James Staunton

  DOI：10.1039/p19810002016

  日期：——

  Many possible 1-benzyltetrahydroisoquinolines have been examined as possible advanced precursors of the alkaloids hasubanonine (1) and protostephanine (2) in Stephania japonica plants, but none was incorporated significantly. Administration of various precursor molecules having only one aromatic ring, such as tyrosine, has demonstrated that both alkaloids are derived from two different C6–C2 biogenetic

  已经研究了许多可能的1-苄基四氢异喹啉类化合物，它们是Stephania japonica植物中生物碱hasubanonine（1）和protostephanine（2）的可能的高级前体，但没有明显掺入。施用仅具有一个芳香环的各种前体分子（例如酪氨酸）已证明这两种生物碱均来自两个不同的C 6 -C 2生物遗传单位。随后无法进一步引入1-苄基四氢异喹啉和双苯乙胺，这表明（a）改性的1-苄基异喹啉或（b）三加氧的C 6 –C 2中间体建筑模块。设计用于检查第一种可能性的前体，例如1-苄基-3,4-二氢异喹啉或1-苄基-1-羧基四氢异喹啉，未合并到（1）和（2）中，而两个3'，4'，5'-掺入三氧化的2-苯基乙胺。这些发现允许进一步描述对生物碱（1）和（2）的后续前体的需求。
• Biosynthesis. Part 25. Proof that hasubanonine and protostephanine are biosynthesised from the 1-benzylisoquinoline system
  作者：Alan R. Battersby、Raymond C. F. Jones、Akwasi Minta、Anthony P. Ottridge、James Staunton

  DOI：10.1039/p19810002030

  日期：——

  described of a set of sixteen 1-benzylisoquinolines and four bisphenethylamines built from 2-(3,4-dihydroxy-5-methoxyphenyl)ethylamine (3), a known biosynthetic precursor to the alkaloids hasubanonine (1) and protostephanine (2) in Stephania japonica plants, and an acid component with a systematically varied oxygenation pattern. Administration of this set of compounds in labelled form to whole plants has

  描述了由16种1-苄基异喹啉和四种由2-（3,4-二羟基-5-甲氧基苯基）乙胺（3）合成的双苯乙胺的合成方法（3），生物碱是已知的生物碱哈苏宁（1）和原草碱（2） ）（Stephania japonica）植物中的酸成分以及系统变化的氧合模式。将这组标记形式的化合物施用于整株植物已导致将六个1-苄基异喹啉并入生物碱中。这些前体中最早的是三酚四氧化异喹啉，并指出了随后的氧化和O-甲基化步骤。N的时机-甲基化不是关键。这些结果需要对早期的生物遗传推测进行微妙的修改，并拒绝某些可能性。Hasubanonine（1）和protostephanine（2）被揭示为1-苄基异喹啉基团的“伪装”成员，其独特之处在于在它们的生物合成过程中，一个环中需要两个酚氧进行氧化偶联。
• 10-substituted 1,8-dihydroxy-9(10H) anthracenone pharmaceuticals
  申请人：Teva Pharmaceutical Industries Ltd.

  公开号：US05952390A1

  公开（公告）日：1999-09-14

  Therapeutic compositions comprising 1,8-dihydoxy-10-\x9b2-(4-methylphenyl)-1-oxoethyl!-9(10H)-anthracenone and (R,S)-1,8-dihydroxy-10-(1-oxo-4-phenylpentyl)-9(10H)-anthracenone, said compounds having substantial therapeutic activity and minimal inflammatory effect.

  治疗性组合物包括1,8-二羟基-10-\x9b2-(4-甲基苯基)-1-氧乙基!-9(10H)-蒽酮和(R,S)-1,8-二羟基-10-(1-氧代-4-苯基戊基)-9(10H)-蒽酮，这些化合物具有显著的治疗活性和最小的炎症作用。
• Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase
  作者：Klaus Mueller、Dieter Guerster、Susanne Piwek、Wolfgang Wiegrebe

  DOI：10.1021/jm00077a015

  日期：1993.12

  The syntheses, the biological evaluation, and the structure-activity relationships of a novel series of 1,8-dihydroxy-9(10H)-anthracenones bearing acyl-, alkyl-, or alkylidene-linked aromatic substituents in the 10-position are described. The phenylacyl and phenylalkylidene analogs were far more potent inhibitors of 5-lipoxygenase (5-LO) from bovine polymorphonuclear leukocytes (IC50 values in the 10(-7) M range) than the antipsoriatic drug anthralin, whereas phenylalkyl analogs were only weak inhibitors. Among the active compounds were both potent generators of hydroxyl radicals, as determined by deoxyribose degradation, and strong reducers of the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH). However, several derivatives of this series maintained 5-LO inhibitory activity but did not generate hydroxyl radicals and were not reactive with DPPH. In particular, phenylacyl analogs were also 6 times more efficient in inhibition of lipid peroxidation in model membranes than anthralin. Structure-activity relationships have shown that the presence of free phenolic groups in the attached aromatic ring is beneficial but not required for 5-LO inhibitory potency. The inhibitory potency in the 10-phenylacyl series increased with the length of the acyl chain with three methylene units being the optimum, suggesting a specific enzyme interaction which would not be expected for nonspecific redox inhibitors.
• Biosynthesis of tylophorine and tylophorinine
  作者：Dewan S. Bhakuni、Virendra K. Mangla

  DOI：10.1016/s0040-4020(01)92028-9

  日期：1981.1

  Administration of 3,4-dihydroxyphenyl[2-14C]alanine to young Tylophora asthmatica plants revealed that ring B and carbon atoms C9 and C7 of tylophorine and tylophorinine [phenanthroin dolizidine alkaloids] are derived from dopa. Tracer experiments with 6,7-diphenylhexahydroindolizines (1-7) and (26) demonstrated that compound 1 is efficiently and specifically incorporated into tylophorine (13) and tylophorinine (16). Compounds (3), (4) and (26) were not metabolized by the plants to form (13) and (16) whereas (5) and (6) were utilized to yield (13) and (16). Compound (2) was very poorly converted into (13) and (16) and thus is not on the major biosynthetic pathway of (13) and (16).