(±)-methyl 2-[3-oxo-2-(2-oxoethyl)cyclopentyl]acetate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (±)-methyl 2-[3-oxo-2-(2-oxoethyl)cyclopentyl]acetate
• 英文别名: methyl 2-[(1S,2S)-3-oxo-2-(2-oxoethyl)cyclopentyl]acetate
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: YSHAJJZKWVTMMV-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (±)-methyl 2-[3-oxo-2-(2-oxoethyl)cyclopentyl]acetate 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 0.5h， 生成 (+/-)-methyl 12-hydroxyjasmonate
  参考文献：
  名称：

  Kitahara,Takeshi; Iwamoto, Minoru; Takagi, Yoshikazu, Agricultural and Biological Chemistry, 1984, vol. 48, # 7, p. 1731 - 1734

  摘要：

  DOI：
• 作为产物：
  描述：

  trans-2-allyl-1-cyclopentanone-3-acetic acid methyl ester 在 臭氧 、 溶剂黄146 、 锌 作用下， 生成 (±)-methyl 2-[3-oxo-2-(2-oxoethyl)cyclopentyl]acetate
  参考文献：
  名称：

  Kitahara,Takeshi; Iwamoto, Minoru; Takagi, Yoshikazu, Agricultural and Biological Chemistry, 1984, vol. 48, # 7, p. 1731 - 1734

  摘要：

  DOI：

文献信息

• Synthesis ofcis-Hedione® and Methyl Jasmonatevia CascadeBaylis-Hillman Reaction andClaisen Ortho Ester Rearrangement
  作者：Christian Chapuis、George H. Büchi、Hans Wüest

  DOI：10.1002/hlca.200590248

  日期：2005.12

  The exocyclically unsaturated conjugated keto esters 10, obtained via a Claisen ortho ester rearrangement of the allylic hydroxy ketones 9, were either directly hydrogenated or partially isomerized into the endocyclically unsaturated tetrasubstituted didehydrojasmonoid intermediates 14, prior to a more selective hydrogenation with Pd/C in cyclohexane to the disubstituted oxocyclopentaneacetates 15

  通过烯丙基羟基酮9的克莱森原酸酯重排而获得的环外不饱和共轭酮酯10直接加氢或部分异构化成环内不饱和四取代的二氢茉莉酮中间体14，然后在环己烷中用Pd / C进行更选择性的氢化。生成二取代的氧代环戊烷乙酸酯15（方案2）。关键中间体9通过四步序列要么获得，包括从烯酮缩醛保护/脱保护1，在羟基酮的特定情况下9A（方案1），或更直接地并且通常是通过环戊-2-en-1-酮（16）和适当的醛17的Baylis-Hillman反应（方案2）。这些醛的明智选择为立体选择性引入部分顺式-或差向异构反式-C（2）茉莉酮类侧链打开了通用的修饰，而手性[1,1'-双萘] -2催化的Baylis-Hillman反应可以以一锅级联方式有效地进行1，2'-二醇（BINOLs）19（方案3），包括原酸酯克莱森重排。
• Qualitative and Quantitative Analysis of Endogenous Jasmonoids in Potato Plant (<i>Solanum tuberosum</i> L.)
  作者：Hideyuki MATSUURA、Fumihiro OHMORI、Masatomo KOBAYASHI、Akira SAKURAI、Teruhiko YOSHIHARA

  DOI：10.1271/bbb.64.2380

  日期：2000.1.1

  Qualitative and quantitative analyses of endogenous jasmonoids were done by liquid chromatography/selected ion monitoring (LC-SIM) using deuterium-labeled compounds as internal standards. To prove the practicality of this way of analyzing the contents of endogenous jasmonoids in plants, the method was used for estimating jasmonoids in potato plants.

  内源性茉莉酸内酯的定性和定量分析是通过液相色谱/选择离子监测（LC-SIM）完成的，其中使用氘标记化合物作为内标。为了证明这种分析植物内源性茉莉酸内酯含量的方法的实用性，该方法被用于估算马铃薯植株中的茉莉酸内酯含量。
• Isolation and Structure Determination of cis-OPDA-α-Monoglyceride from Arabidopsis thaliana
  作者：Shotaro Hirota、Yusuke Ito、Shiro Inoue、Naoki Kitaoka、Tohru Taniguchi、Kenji Monde、Kosaku Takahashi、Hideyuki Matsuura

  DOI：10.1021/acs.jnatprod.3c01237

  日期：2024.5.24

  cis-12-oxo-Phytodieneoic acid-α-monoglyceride (1) was isolated from Arabidopsis thaliana. The chemical structure of 1 was elucidated based on exhaustive 1D and 2D NMR spectroscopic measurements and supported by FDMS and HRFDMS data. The absolute configuration of the cis-OPDA moiety in 1 was determined by comparison of 1H NMR spectra and ECD measurements. With respect to the absolute configuration of

  顺式-12-氧代-植物二烯酸-α-单甘油酯( 1 )是从拟南芥中分离出来的。 1的化学结构是基于详尽的 1D 和 2D NMR 光谱测量并得到 FDMS 和 HRFDMS 数据的支持而阐明的。 1中顺式-OPDA 部分的绝对构型通过比较1 H NMR 谱和 ECD 测量来确定。关于甘油主链β位的绝对构型，通过与( R )-(+)-α-甲氧基-制备酯键衍生物来确定( S )与( R )的2:3比例。 α-三氟甲基苯乙酰氯并比较1 H NMR 谱。创伤应激不会增加1的内源水平，并且表明1对拟南芥发芽后生长具有抑制作用。值得注意的是，完整植物中1的内源量高于(+)-7-异茉莉酸和(+)-顺式-OPDA的量。 1还表现出对革兰氏阳性菌的抗菌活性，但茉莉酸却没有。还发现α-亚麻酸-α-单甘油酯在拟南芥植物中转化为1 ，这表明α-亚麻酸-α-单甘油酯是1的生物合成中间体。
• Direct observation of the target cell for jasmonate-type leaf-closing factor: genus-specific binding of leaf-movement factors to the plant motor cell
  作者：Yoko Nakamura、Hiromasa Kiyota、Tsutomu Kumagai、Minoru Ueda

  DOI：10.1016/j.tetlet.2006.02.123

  日期：2006.4

  We report the synthesis of the novel fluorescence-labeled jasmonate glycoside 2 based on beta-D-glucopyranosyl 12-hydroxy-jasmonate 1, which is a leaf-closing substance of Albizzia Durazz. The fluorescence study using 2 revealed that the target cell for 1 is a motor cell. Probe 2 bound to the motor cells of two plants belonging to genus Albizzia. This result suggested that a receptor for 2, which is common among genus Albizzia would be involved in the nyctinastic leaf movement. (c) 2006 Elsevier Ltd. All rights reserved.
• Enantio-differential approach to identify the target cell for glucosyl jasmonate-type leaf-closing factor, by using fluorescence-labeled probe compounds
  作者：Yoko Nakamura、Ryoji Miyatake、Akira Matsubara、Hiromasa Kiyota、Minoru Ueda

  DOI：10.1016/j.tet.2006.06.092

  日期：2006.9

  Potassium beta-D-glucopyranosyl 12-hydroxyjasmonate (1) is a leaf-closing factor of Albizzia plants that induces nyctinastic leaf closure. In this paper, we synthesized probe 3 and its congener 4 by using a pair of enantiomerically pure methyljasmonate that was prepared by using optical resolution, and carried out fluorescence studies using 3 and 4 to identify the target cell of 1. The probe 3 bound to the motor cells of two Albizzia plants, whereas it could not bind to the motor cells of plants belonging to other genus. On the other hand, probe 4 did not bind to the motor cell at all. These results suggested that a specific receptor for I is involved in the motor cell of Albizzia plants. (c) 2006 Elsevier Ltd. All rights reserved.