(4-nitrobenzyl) E-2-methylbutenoate | 89169-66-4

• 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: (4-nitrobenzyl) E-2-methylbutenoate
• 英文别名: p-nitrobenzyl ester of tiglic acid；p-Nitrobenzyl-tiglat；tiglic acid p-nitrobenzyl ester；(4-nitrophenyl)methyl (E)-2-methylbut-2-enoate
• CAS: 89169-66-4
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: NOEDFNKVZOISPZ-YCRREMRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  22-O-tigloylbarrigenol A1 3-O-[β-D-galactopyranosyl(1->2)] [β-D-xylopyranosyl(1->2)-α-L-arabinopyranosyl(1->3)]-β-D-glucopyranosiduronic acid 在 desacylchakasaponin IV 、 水 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 (4-nitrobenzyl) E-2-methylbutenoate
  参考文献：
  名称：

  药用花。XXXIII。茶树皂苷I-III的降脂和降糖作用以及茶树（Camellia sinensis）花蕾中茶碱皂苷IV的结构。

  摘要：

  研究了来自中国福建省茶树的花蕾中的主要皂苷，chakasaponins I-III对载有橄榄油或蔗糖的小鼠血浆甘油三酸酯（TG）和葡萄糖水平的影响。Chakasaponins I-III的浓度为50和100 mg / kg，可显着抑制血浆TG和葡萄糖水平的升高。此外，它们阻止了胃排空，表明前者的抑制作用部分取决于对胃排空的抑制。此外，基于化学和物理化学证据，阐明了一种新的酰化的齐墩果烷型三萜寡糖甙，chakasaponin IV的化学结构。

  DOI：

  10.1248/cpb.60.674

文献信息

• Medicinal Flowers. XXXVI.<sup>1</sup><sup>)</sup> Acylated Oleanane-Type Triterpene Saponins with Inhibitory Effects on Melanogenesis from the Flower Buds of Chinese <i>Camellia japonica</i>
  作者：Seikou Nakamura、Katsuyoshi Fujimoto、Souichi Nakashima、Takahiro Matsumoto、Tomoko Miura、Kaoru Uno、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1248/cpb.60.752

  日期：——

  Four acylated oleanane-type triterpene oligoglycosides, sanchakasaponins E–H, were isolated from the flower buds of Camellia japonica cultivated in Yunnan province, China, together with four known triterpene oligoglycosides. The chemical structures of the new triterpene oligoglycosides were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of the triterpene oligoglycoside constituents on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells were investigated.

  从中国云南省栽培的茶花花蕾中分离得到4个酰化的齐墩果烷型三萜低聚糖苷——山茶皂苷E~H，以及4个已知的三萜低聚糖苷。通过化学和物理化学证据阐明了新三萜低聚糖苷的化学结构。研究了这些三萜低聚糖苷组分对茶碱刺激的B16黑色素瘤4A5细胞黑素生成的抑制作用。
• Asymmetric Hydrogenation Routes to Deoxypolyketide Chirons
  作者：Jianguang Zhou、James W. Ogle、Yubo Fan、Vorawit Banphavichit(Bee)、Ye Zhu、Kevin Burgess

  DOI：10.1002/chem.200700390

  日期：2007.8.27

  selectivity; this is the first time this has been achieved in any asymmetric synthesis of a deoxypolyketide fragment. Throughout, diastereoselectivities of the crude material in the syntheses of alpha,omega-functionalized internal deoxypolyketide fragments were in excess of 11:1.0 and chromatographically purified samples could be isolated in high yields with dr (dr=diastereomeric ratio) values consistently

  进行单烯和二烯的不对称氢化以获得末端脱氧聚酮片段A以及相应的内部Chiron B和C。整个使用手性N-杂环卡宾催化剂1。简单的单烯的氢化反应的适度选择性转为制备末端脱氧聚酮化合物片段的高选择性，其中使用两个氢化反应或一个和一个光学纯的起始原料。奇怪的是，α，β-不饱和酯加氢的表面选择性一直与先前研究中苯乙烯和苯乙烯衍生物的观察结果相反，并且与这项研究中紧密相关的烯丙醇和醚衍生物也一直相反。通过使用DFT计算得出了这种不同行为的合理机制。看来酯衍生物异常立体选择性的起源是酯羰基的瞬时金属配位，而没有证据表明烯丙基醇或醚配位。发展为α，ω-官能化的内部脱氧聚酮片段的途径是非常实用的。这些始于将罗氏酯转化为烯烃，在一种情况下，转化为二烯衍生物。在这些底物的氢化中主要控制催化剂，但是存在显着的“底物载体”（我们用来描述底物对催化剂控制的反应的影响的术语）。这是通过最小化1,3-烯丙基菌株以及在某些
• Acylated Oleanane-Type Triterpene Saponins with Acceleration of Gastrointestinal Transit and Inhibitory Effect on Pancreatic Lipase from Flower Buds of Chinese Tea Plant (<i>Camellia sinensis</i>)
  作者：Masayuki Yoshikawa、Sachiko Sugimoto、Yasuyo Kato、Seikou Nakamura、Tao Wang、Chihiro Yamashita、Hisashi Matsuda

  DOI：10.1002/cbdv.200800153

  日期：2009.6

  extract and its BuOH-soluble fraction (crude saponin fraction) from the flower buds of Chinese tea plant (Camellia sinensis (L.) O. KUNTZE; Fujian Province) were found to exhibit accelerating effects on gastrointestinal transit in mice and inhibitory effects against pancreatic lipase. From the BuOH-soluble fraction, three new acylated oleanane-type triterpene oligoglycosides, chakasaponins I, II, and

  发现来自中国茶树（Camellia sinensis (L.) O. KUNTZE；福建省）花蕾的 MeOH 提取物及其 BuOH 可溶部分（粗皂苷部分）对小鼠胃肠道传输具有加速作用和抑制作用对抗胰脂肪酶。从 BuOH 可溶部分中，分离出三种新的酰化齐墩果型三萜低聚糖苷、chakasaponins I、II 和 III (1-3，分别) 和 13 种已知化合物。在化学和物理化学证据的基础上阐明了化学结构1-3。化合物 1-3 显示出对小鼠胃肠道转运的加速作用和对猪胰脂肪酶的抑制作用 (IC(50)=150-530 microM)。
• Medicinal Flowers. XXII. Structures of Chakasaponins V and VI, Chakanoside I, and Chakaflavonoside A from Flower Buds of Chinese Tea Plant (Camellia sinensis)
  作者：Masayuki Yoshikawa、Sachiko Sugimoto、Seikou Nakamura、Hisashi Matsuda

  DOI：10.1248/cpb.56.1297

  日期：——

  Two acylated oleanane-type triterpene oligoglycosides, chakasaponins V and VI, an aromatic glycoside, chakanoside I, and an acylated flavonol oligoglycoside, chakaflavonoside A, were isolated from the flower buds of Chinese tea plant [Camellia sinensis (L.) O. KUNTZE]. The chemical structures of those new glycosides were elucidated on the basis of chemical and physicochemical evidence.

  从中国茶树[Camellia sinensis（L.）O. KUNTZE]的花蕾中分离出两种酰化的齐墩果烷型三萜寡糖苷，chakasaponins V和VI，一种芳香族糖苷，chakanoside I，一种酰化的黄酮寡糖苷，chakaflavonosideA。 。在化学和物理化学证据的基础上阐明了这些新糖苷的化学结构。
• Medicinal Flowers. XXXV. Nor-oleanane-type and acylated oleanane-type triterpene saponins from the flower buds of Chinese &lt;i&gt;Camellia japonica&lt;/i&gt; and their inhibitory effects on melanogenesis&lt;sup&gt;1)&lt;/sup&gt;
  作者：Katsuyoshi Fujimoto、Seikou Nakamura、Souichi Nakashima、Takahiro Matsumoto、Kaoru Uno、Tomoe Ohta、Tomoko Miura、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1248/cpb.c12-00473

  日期：——

  The methanolic extract and its 1-butanol-soluble fraction from the flower buds of Camellia japonica, cultivated in Yunnan Province, China, showed inhibitory effects on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the 1-butanol-soluble fraction, a new 28-nor-oleanane-type and three new oleanane-type triterpene saponins, sanchakasaponins A–D, were isolated together with four known triterpene saponins. Their chemical structures were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells and structure–activity relationships of the saponins were investigated.

  从中国云南省栽培的山茶花花蕾中提取的甲醇提取物及其1-丁醇-可溶性馏分对茶碱刺激的B16黑色素瘤4A5细胞的黑色素生成有抑制作用。从 1-丁醇可溶性馏分中分离出了一种新的 28-去油烷型和三种新的去油烷型三萜皂苷，即三七皂苷 A-D，以及四种已知的三萜皂苷。根据化学和物理化学证据，阐明了它们的化学结构。研究了这些皂甙对茶碱刺激的 B16 黑色素瘤 4A5 细胞黑色素生成的抑制作用及其结构-活性关系。