methyl (1S,2S)-3-oxo-2-(formylmethyl)cyclopentaneacetate | 202973-91-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1S,2S)-3-oxo-2-(formylmethyl)cyclopentaneacetate
• 英文别名: 2,3-trans-3-Carbomethoxymethyl-2-formylmethyl-cyclopentanon-1；(1R,2R)-methyl 3-oxo-2-(2-oxoethyl)-1-cyclopentaneacetate；methyl 2-[(1R,2R)-3-oxo-2-(2-oxoethyl)cyclopentyl]acetate
• CAS: 202973-91-9
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: YSHAJJZKWVTMMV-HTQZYQBOSA-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 (1S,2S)-3-oxo-2-(formylmethyl)cyclopentaneacetate 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 0.17h， 生成 methyl 12-hydroxyjasmonate
  参考文献：
  名称：

  Enantio-differential approach to identify the target cell for glucosyl jasmonate-type leaf-closing factor, by using fluorescence-labeled probe compounds

  摘要：

  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.

  DOI：

  10.1016/j.tet.2006.06.092
• 作为产物：
  描述：

  茉莉酸甲酯 在 臭氧 、 二甲基硫 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以98%的产率得到methyl (1S,2S)-3-oxo-2-(formylmethyl)cyclopentaneacetate
  参考文献：
  名称：

  Enantio-differential approach to identify the target cell for glucosyl jasmonate-type leaf-closing factor, by using fluorescence-labeled probe compounds

  摘要：

  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.

  DOI：

  10.1016/j.tet.2006.06.092

文献信息

• 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.