2-pentadecyl-resorcinol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-pentadecyl-resorcinol
• 英文别名: 2-Pentadecyl-resorcin；pentadecylresorcinol；2-pentadecylbenzene-1,3-diol
• 化学式: C₂₁H₃₆O₂
• 分子量: 320.516
• InChiKey: NLCUMKKFPDGYTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,3-dimethoxy-2-pentadec-1-enyl-benzene 在 palladium on activated charcoal 、 三氯化铝 、 乙酸乙酯 、 氯苯 作用下， 生成 2-pentadecyl-resorcinol
  参考文献：
  名称：

  Synthesis of the Mono- and Dihydric Pentadecylphenols Related to Poison Ivy “Urushiol”

  摘要：

  DOI：

  10.1021/ja01597a060

文献信息

• Two Novel Alkylresorcinol Synthase Genes from Sorghum; Cloning, Expression, Transformation and Characterization
  申请人：Baerson Scott R.

  公开号：US20110225676A1

  公开（公告）日：2011-09-15

  Sorghum is considered to be an allelopathic crop species, producing phytotoxins such as the lipid benzoquinone sorgoleone (2-hydroxy-5-methoxy-3-[(Z,Z)-8′,11′,14′-pentadecatriene]-p-benzoquinone) which likely accounts for much of its allelopathic properties. Prior investigations into the biosynthesis of sorgoleone have suggested the participation of one or more alkylresorcinol synthases (ARS), which are type III polyketide synthases (PKS) that produce 5-alkylresorcinols using medium to long-chain fatty acyl-CoA starter units via iterative condensations with malonyl-CoA. Current evidence suggests that sorgoleone biosynthesis occurs exclusively in root hair cells, involving the synthesis of a 5-pentadecatrienyl resorcinol intermediate derived from an unusual 16:3 fatty acyl-CoA starter unit. To characterize the enzymes responsible for the biosynthesis of this alkylresorcinol intermediate, a previously-described expressed sequence tag (EST) database prepared from isolated root hairs was first mined for all PKS-like sequences. Quantitative real-time RT-PCR analyses revealed that two of these sequences were preferentially expressed in root hairs, and recombinant enzyme studies demonstrated that both sequences (designated ARS1 and ARS2) encode ARS enzymes capable of accepting a variety of fatty acyl-CoA starter units. Furthermore, RNA interference (RNAi) experiments directed against ARS1 and ARS2 resulted in the generation of multiple independent transformant events exhibiting dramatically reduced sorgoleone levels. Thus, both ARS1 and ARS2 are likely to participate in the biosynthesis of sorgoleone in planta. The sequences of ARS1 and ARS2 were also used to identify several rice genes encoding ARSs, which are likely involved in the production of defense-related alkylresorcinols.

  高粱被认为是一种化感作物，产生植物毒素，如脂肪苯醌sorgoleone（2-羟基-5-甲氧基-3-[(Z，Z)-8'，11'，14'-十五碳烯三烯基]-p-苯醌），这很可能解释了其大部分化感特性。对sorgoleone生物合成的先前研究表明，参与其中的是一种或多种烷基间苯酚合酶（ARS），它们是III型聚酮合酶（PKS），使用中到长链脂肪酰辅酶A起始单元通过与丙酰辅酶A的迭代缩合产生5-烷基间苯酚。目前的证据表明，sorgoleone生物合成仅发生在根毛细胞中，涉及从不寻常的16：3脂肪酰辅酶A起始单元衍生的5-十五碳烯三烯基间苯酚中间体的合成。为了表征负责合成这种烷基间苯酚中间体的酶，首先从分离的根毛制备的已描述表达序列标签（EST）数据库中挖掘所有类似于PKS的序列。定量实时RT-PCR分析表明，其中两个序列在根毛中优先表达，重组酶研究表明这两个序列（称为ARS1和ARS2）编码的ARS酶能够接受各种脂肪酰辅酶A起始单元。此外，针对ARS1和ARS2的RNA干扰（RNAi）实验导致产生多个独立的转化事件，其sorgoleone水平显著降低。因此，ARS1和ARS2都可能参与植物中sorgoleone的生物合成。ARS1和ARS2的序列还用于鉴定编码ARS的几个水稻基因，这些基因可能参与产生与防御相关的烷基间苯酚。
• Functionalized peroxides for polymerization reactions
  申请人：ELF ATOCHEM NORTH AMERICA, INC.

  公开号：EP0474227A1

  公开（公告）日：1992-03-11

  Novel functionalized peroxides which may be used as crosslinking, grafting and curing agents, initiators for polymerization reactions and as monomers for condensation polymerizations to form peroxy-containing polymers, which in turn can be used to prepare block and graft copolymers, have the following Formula I:    R¹, R², R³, R⁴, R⁵, R⁶, R⁷, X, Y¹, Y², Y³, Z¹, Z², x, y and z are as defined in the Summary of the Invention. The compounds of Formula I may be prepared by reacting hydroxy-containing tertiary hydroperoxides with diacid halides, phosgene, dichloroformates, diisocyanates, anhydrides and lactones to form the functionalized peroxides. These reaction products may be further reacted, if desired, with dialcohols, diamines, aminoalcohols, epoxides, epoxy alcohols, epoxy amines, diacid halides, dichloroformates and diisocyanates to form additional functionalized peroxides.

  新型官能化过氧化物可用作交联剂、接枝剂和固化剂、聚合反应的引发剂以及缩合聚合的单体，从而形成含过氧化物的聚合物，进而可用于制备嵌段和接枝共聚物： R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、X、Y¹、Y²、Y³、Z¹、Z²、x、y 和 z 如发明概述中所定义。 式 I 的化合物可通过使含羟基的叔氢过氧化物与二酸卤化物、光气、二氯甲烷、二异氰酸酯、酸酐和内酯反应形成官能化过氧化物来制备。如果需要，这些反应产物还可以进一步与二醇、二胺、氨基醇、环氧化物、环氧醇、环氧胺、二酸卤化物、二氯甲烷酸盐和二异氰酸酯反应，形成更多的官能化过氧化物。
• Polymeric peroxides derived from hydroxy-hydroperoxides and dihydroxy-dialkyl peroxides and their use
  申请人：ELF ATOCHEM NORTH AMERICA, INC.

  公开号：EP0472819A2

  公开（公告）日：1992-03-04

  A polymeric peroxide comprising a divalent recurring unit having the formula: wherein the recurring unit of Formula I has a 10 hour half-life temperature of at least 80 °C and optionally a divalent recurring unit having the formula: wherein R1, R2, R3, R5, X, X1, Y, Z, y and z are as defined in the Detailed Description of the Preferred Embodiments and the polymeric peroxide has a molecular weight of 1,000 to 200,000. The polymeric peroxides are derived from hydroxy-hydroperoxides or dihydroxy dialkyl peroxides. These polymeric peroxides can be used for preparing block copolymers and compatibilizing polymer blends and alloys.

  一种聚合过氧化物，包含具有以下式子的二价递归单元 其中式 I 的递归单元的 10 小时半衰期温度至少为 80℃，可选地还包括具有式 其中 R1、R2、R3、R5、X、X1、Y、Z、y 和 z 如优选实施例的详细说明中所定义，聚合过氧化物的分子量为 1,000 至 200,000。聚合过氧化物由羟基氢过氧化物或二羟基二烷基过氧化物衍生而来。这些聚合过氧化物可用于制备嵌段共聚物和相容聚合物混合物及合金。
• US5039754A
  申请人：——

  公开号：US5039754A

  公开（公告）日：1991-08-13
• US5250494A
  申请人：——

  公开号：US5250494A

  公开（公告）日：1993-10-05