ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate | 188945-44-0

• 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: ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate
• 英文别名: Ethyl-di-(2-isopropylphenyl)phosphonoacetate；ethyl 2-bis(2-propan-2-ylphenoxy)phosphorylacetate
• CAS: 188945-44-0
• 化学式: C₂₂H₂₉O₅P
• 分子量: 404.443
• InChiKey: ZBJOYTOFBGFNDO-UHFFFAOYSA-N

物化性质

• 沸点：
  489.0±45.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate 在 苄基三甲基氢氧化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 4.0h， 生成 (Z)-5-phenylpent-2-enoic acid
  参考文献：
  名称：

  (2Z,4E)-5-苯基五-2,4-二烯酸抑制根向地性的基本结构特征

  摘要：

  此前，我们发现 (2Z,4E)-5-苯基五-2,4-二烯酸 (ku-76) 在 5 μM 浓度下是生菜胚根根向重力弯曲的选择性抑制剂，但没有伴随的生长抑制。在这里，我们描述了 ku-76 的结构-活性关系研究，以确定抑制活性的基本结构特征。合成了一系列 ku-76 类似物，并确定了抑制生菜根向重力弯曲所需的 ku-76 关键特征。 (2E,4E)-、(2Z,4Z)- (2E,4Z)- 类似物无活性，4,5-饱和和 4,5-炔基类似物也不显示抑制活性，这证明了 (2E,4Z)- 类似物的重要性（ 2Z,4E)二烯单元。芳环也很重要，不能用烷基链代替。羧酸被酰胺、醇或酯取代的衍生物的效力要低得多。这些结果表明，(2Z,4E)-二烯、羧酸部分和芳环对于对向重力弯曲的有效抑制活性至关重要。

  DOI：

  10.1016/j.phytochem.2020.112287
• 作为产物：
  描述：

  异丙苯酚 、 ethyl dichlorophosphonoacetate 在 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 以55%的产率得到ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate
  参考文献：
  名称：

  通过使用新的霍纳-埃蒙斯试剂（乙基二芳基膦酸酯）乙酸乙酯，高度选择性地合成Z-不饱和酯。

  摘要：

  由膦酸三乙酯，PCl（5）和相应的酚制备新的Horner-Emmons试剂（二芳基膦酸乙酯）乙酸乙酯1。在Triton B或NaH存在下，THF中1与几种醛的反应表明，这些试剂可用于合成Z-不饱和酯。在所检查的试剂中，发现乙基（二-邻甲苯基膦酰基）-，[双（邻乙基苯基）膦基]-和[双（邻异丙基苯基）膦基]乙酸酯（1k-m）最有效，得到Z-不饱和酯，选择性为93-99％。

  DOI：

  10.1021/jo970057c

文献信息

• シス桂皮酸類縁体、重力屈性調節剤
  申请人：国立大学法人東京農工大学

  公开号：JP2019189648A

  公开（公告）日：2019-10-31

  【課題】シス桂皮酸又は桂皮酸類縁体を含む重力屈性調節剤の提供。【解決手段】シス桂皮酸及び/又は桂皮酸類縁体を有効成分として含む重力屈性調節剤であり、桂皮酸類縁体は、例えば下記の反応式によって得られる化合物が挙げられる。（上式中、Ｒはフェニル基を示す。）【選択図】図６

  提供含有類似桂皮酸或類似桂皮酸衍生物的重力調節劑。該重力調節劑包含cis桂皮酸和/或類似桂皮酸衍生物作為有效成分，其中類似桂皮酸衍生物可通過以下反應式獲得的化合物為例。（在上述式中，R代表苯基。）【選擇圖】圖6
• Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity
  作者：Mitsuru Shindo、Saki Makigawa、Kozue Kodama、Hiromi Sugiyama、Kenji Matsumoto、Takayuki Iwata、Naoya Wasano、Arihiro Kano、Miyo Terao Morita、Yoshiharu Fujii

  DOI：10.1016/j.phytochem.2020.112508

  日期：2020.11

  structure-activity relationship in this inhibitory activity. The conformation of ku-76 is flexible owing to the open-chain structure of pentan-2,4-dienoic acid with freely rotating single bonds, and the (2Z)-alkene moiety may be isomerized by external factors. To develop more potent inhibitors and obtain insight into the target biomolecules, various analogues of ku-76, fixed through conformation and/or

  此前，我们发现 (2Z,4E)-5-苯基五-2,4-二烯酸 (ku-76) 在 5 μM 浓度下是生菜胚根根向重力弯曲的选择性抑制剂，且不伴随生长抑制，并揭示了该抑制活性中的构效关系。由于戊-2,4-二烯酸具有自由旋转单键的开链结构，ku-76的构象是灵活的，并且(2Z)-烯烃部分可以通过外部因素异构化。为了开发更有效的抑制剂并深入了解目标生物分子，合成并评估了通过构象和/或构型固定的 ku-76 的各种类似物。立体化学固定可有效提高向地弯曲抑制的效力。最后，我们发现了高效的构象和/或构型类似物（ku-257、ku-294 和 ku-30​​8），它们不会抑制根的生长。这些类似物对根部弯曲的抑制作用与抑菌灵相当。
• <i>cis</i>-Cinnamic Acid Selective Suppressors Distinct from Auxin Inhibitors
  作者：Katsuhiro Okuda、Keisuke Nishikawa、Hiroshi Fukuda、Yoshiharu Fujii、Mitsuru Shindo

  DOI：10.1248/cpb.c14-00169

  日期：——

  The activity of cis-cinnamic acid (cis-CA), one of the allelochemicals, in plants is very similar to that of indole-3-acetic acid (IAA), a natural auxin, and thus cis-CA has long been believed to be an analog of auxin. We have reported some structure–activity relationships studies by synthesizing over 250 cis-CA derivatives and estimating their inhibitory activities on root growth inhibition in lettuce. In this study, the compounds that showed low- or no-activity on root growth inhibition were recruited as candidates suppressors against cis-CA and/or auxin and tested for their activity. In the presence of cis-CA, lettuce root growth was inhibited; however, the addition of some cis-CA derivatives restored control-level root growth. Four compounds, (Z)-3-(4-isopropylphenyl)acrylic acid, (Z)-3-(3-butoxyphenyl)acrylic acid, (Z)-3-[3-(pentyloxy)phenyl]acrylic acid, and (Z)-3-(naphthalen-1-yl)acrylic acid were selected as candidates for a cis-CA selective suppressor they allowed the recovery of root growth from inhibition by cis-CA treatment without any effects on the IAA-induced effect or elongating activity by themselves. Three candidates significantly ameliorated the root shortening by the potent inhibitor derived from cis-CA. In brief, we have found some cis-CA selective suppressors which have never been reported from inactive cis-CA derivatives for root growth inhibition. cis-CA selective suppressors will play an important role in elucidating the mechanism of plant growth regulation.

  等位化学物质之一的顺式肉桂酸（cis-CA）在植物体内的活性与天然辅助素吲哚-3-乙酸（IAA）非常相似，因此顺式肉桂酸一直被认为是辅助素的类似物。我们合成了 250 多种顺式-CA 衍生物，并估算了它们对莴苣根系生长的抑制活性，从而报告了一些结构-活性关系研究。在本研究中，我们将对根系生长抑制活性低或无活性的化合物作为顺式 CA 和/或辅助素的候选抑制剂，并对其活性进行了测试。在存在顺式-CA 的情况下，莴苣根系生长受到抑制；然而，添加一些顺式-CA 衍生物后，根系生长恢复到控制水平。(Z)-3-(4-异丙基苯基)丙烯酸、(Z)-3-(3-丁氧基苯基)丙烯酸、(Z)-3-[3-(戊氧基)苯基]丙烯酸和(Z)-3-(萘-1-基)丙烯酸这四种化合物被选为顺式-CA 选择性抑制剂的候选化合物。三种候选物质能明显改善顺式-CA 衍生的强效抑制剂对根缩短的影响。总之，我们从无活性的顺式 CA 衍生物中发现了一些从未报道过的抑制根生长的顺式 CA 选择性抑制剂。
• Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors
  作者：Keisuke Nishikawa、Hiroshi Fukuda、Masato Abe、Kazunari Nakanishi、Tomoya Taniguchi、Takashi Nomura、Chihiro Yamaguchi、Syuntaro Hiradate、Yoshiharu Fujii、Katsuhiro Okuda、Mitsuru Shindo

  DOI：10.1016/j.phytochem.2013.08.013

  日期：2013.12

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.
• Key structural features of cis-cinnamic acid as an allelochemical
  作者：Masato Abe、Keisuke Nishikawa、Hiroshi Fukuda、Kazunari Nakanishi、Yuta Tazawa、Tomoya Taniguchi、So-young Park、Syuntaro Hiradate、Yoshiharu Fujii、Katsuhiro Okuda、Mitsuru Shindo

  DOI：10.1016/j.phytochem.2012.08.001

  日期：2012.12

  1-O-cis-cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals isolated from Spiraea thunbergii Sieb. It is suggested that it derives its strong inhibitory activity from cis-cinnamic acid, which is crucial for phytotoxicity. It was synthesized to confirm its structure and bioactivity, and also a series of cis-cinnamic acid analogues were prepared to elucidate the key features of cis-cinnamic acid for lettuce root growth inhibition. The cis-cyclopropyl analogue showed potent inhibitory activity while the saturated and alkyne analogues proved to be inactive, demonstrating the importance of the as-double bond. Moreover, the aromatic ring could not be replaced with a saturated ring. However, the 1,3-dienylcyclo-hexene analogue showed strong activity. These results suggest that the geometry of the C-C double bond between the carboxyl group and the aromatic ring is essential for potent inhibitory activity. In addition, using several light sources, the photostability of the cinnamic acid derivatives and the role of the C-C double bond were also investigated. (c) 2012 Elsevier Ltd. All rights reserved.