2-氰基-N-(3-溴苯基)-乙酰胺 | 63038-10-8

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 中文名称: 2-氰基-N-(3-溴苯基)-乙酰胺
• 中文别名: (3S)-3-丁基-4,5-二氢-1(3H)-异苯并呋喃酮
• 英文名称: senkyunolide A
• 英文别名: senkyunolide；(3S)-3-butyl-4,5-dihydro-3H-2-benzofuran-1-one
• CAS: 63038-10-8
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: ZPIKVDODKLJKIN-NSHDSACASA-N

物化性质

• 溶解度：
  DMF：5mg/mL； DMSO：5mg/mL；乙醇：30mg/mL；乙醇:PBS(pH 7.2) (1:1): 0.5 mg/ml
• LogP：
  1.775 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932209090
• 储存条件：
  2-8℃

制备方法与用途

生物活性 Senkyunolide A 是从川芎中分离得到的一种具有细胞保护、抗增殖及抗肿瘤活性的化合物。

化学性质 微黄色油状物，能溶于甲醇、乙醇和DMSO等有机溶剂，来源于川芎根茎。

用途 洋川芎内酯A 具有抗脑缺血和防治老年痴呆的作用，并能抑制子宫节律性收缩。

反应信息

• 作为反应物：
  描述：

  2-氰基-N-(3-溴苯基)-乙酰胺 在 4-二甲氨基吡啶 吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 Senkyunolide J p-bromobenzoate
  参考文献：
  名称：

  川芎中的两种苯酞

  摘要：

  从川芎的根茎中分离到了两种新的苯酞，senkyunolides R 和 S。通过光谱分析和化学方法，证明了仙九内酯R和仙九内酯S的结构为(6RS,7RS,9SR)-3-丁叉-4,5,6,7-四氢-6,7,9-三羟基邻苯二甲酸酯和 (6RS,7RS,9RS)-3-丁叉基-4,5,6,7-四氢-6,7,9-三羟基邻苯二甲酸酯，分别。

  DOI：

  10.1016/0031-9422(92)90051-q
• 作为产物：
  描述：

  (S)-(-)-1-ethynylpentyl 2,4-pentadienoate 在 抗氧剂300 作用下， 以 甲苯 为溶剂， 反应 9.0h， 以43%的产率得到2-氰基-N-(3-溴苯基)-乙酰胺
  参考文献：
  名称：

  芝麻烯内酯的不对称合成和感官评估。

  摘要：

  描述了对苯二酚内酯（1）和3-丁基邻苯二甲酸酯（3）的对映体的合成和感官评价。不对称合成通过手性炔丙基酯（5）的分子内Diels-Alder反应实现，该手性炔丙基酯由旋光的炔丙醇（4）和2,4-戊二烯酸制备。这些对映体的感官评估表明，它们的香气特征和气味阈值之间存在明显差异。

  DOI：

  10.1271/bbb.110206

文献信息

• Studies on the constituents of umbelliferae plants. XV Constituents of Cnidium officinale : Occurrence of pregnenolone, coniferylferulate and hydroxyphthalides.
  作者：MASARU KOBAYASHI、MIYUKI FUJITA、HIROSHI MITSUHASHI

  DOI：10.1248/cpb.35.1427

  日期：——

  Pregnenolone (1), coniferylferulate (2) and nine mono-and dihydroxyphthalide derivatives (5-13) were isolated from the commercial C. officinale rhizome. Their structures were determined from the spectroscopic data and the dihydroxyphthalides senkyunolide-H (11) and-I (12) and senkyunolide-J (13) were synthesized from the major components ligustilide (14) and senkyunolide-A (16), respectively. These oxygenated phthalides were absent in the fresh C. officinale rhizome and they were shown to be derived from the major volatile phthalides during storage of the crude drug. Coniferylferulate (2) also decomposes partly during storage, giving ferulic acid.

  从市售的当归根茎中分离得到娠烯醇酮（1）、松柏苷（2）和9个单羟基和二羟基苯酞衍生物（5-13）。通过光谱数据确定了它们的结构，其中二羟基苯酞素芹子醇-H（11）、-I（12）和芹子醇-J（13）分别由主要成分藁本内酯（14）和芹子醇-A（16）合成得到。这些氧化的苯酞在新鲜的当归根茎中不存在，它们是在药材储存过程中由主要挥发性苯酞衍生而来。松柏苷（2）在储存过程中也部分分解为阿魏酸。
• Phthalide Dimers from Ligusticum chuangxiong Hort.
  作者：Takashi Naito、Takao Katsuhara、Kazuaki Niitsu、Yukinobu Ikeya、Minoru Okada、Late Hiroshi Mitsuhashi

  DOI：10.3987/com-91-5877

  日期：——

  Two new phthalide dimers, senkyunolide 0 (1) and senkyunolide P (2), along with three known phthalide dimers were isolated from the rhizome of Ligusticum chuangxiong Hort. On the basis of spectral analyses and chemical methods, the structures of these compounds were determined.
• NOVEL USE OF ORGANIC COMPOUNDS
  申请人：Fowler Ann

  公开号：US20090176873A1

  公开（公告）日：2009-07-09

  The present invention relates to the use of compounds of the formula (I) wherein the clotted line is an optional bond; R 1 is butyl or butyryl if R 2 is hydroxyl but is butyl if R 2 is hydrogen; or R 1 and R 2 taken together are 1-butylidene optionally substituted by hydroxyl, methyl, or 3-(α,β-dimethylacrylyloxy)-pentylidenyl; X is a residue selected from the group consisting of X1, X2, X3, X4, and X5; wherein X is X2, X3 or X5 if the dotted line in formula (I) is absent; and X is X1, X4 or X5 if the dotted line signifies a bond in formula (I) above; R 3 is hydroxyl or butyryl; and n is 1 or 2, as agents for the prevention, control and treatment of conditions requiring modulation of inflammation in mammals. In another aspect, the present invention relates to the use of compounds of the formula (I) as active ingredients in the manufacture of medicaments/compositions for the prevention, control and treatment of conditions requiring modulation of inflammation. The compounds of formula (I) as defined above may also be useful (for the manufacture of a composition) for the management of pain, fever and injuries, especially sport injuries. Moreover, the compounds of formula (I) as defined above may also be useful (for the manufacture of a composition) for the maintenance and regeneration of articular cartilage.
• Anti-inflammatory compositions and their use
  申请人：Fowler Ann

  公开号：US20100298427A1

  公开（公告）日：2010-11-25

  The present invention relates to the use of compounds of the formula (I) wherein the clotted line is an optional bond; R 1 is butyl or butyryl if R 2 is hydroxyl but is butyl if R 2 is hydrogen; or R 1 and R 2 taken together are 1-butylidene optionally substituted by hydroxyl, methyl, or 3-(α,β-dimethylacrylyloxy)-pentylidenyl; X is a residue selected from the group consisting of X1, X2, X3, X4, and X5; wherein X is X2, X3 or X5 if the dotted line in formula (I) is absent; and X is X1, X4 or X5 if the dotted line signifies a bond in formula (I) above; R 3 is hydroxyl or butyryl; and n is 1 or 2, as agents for the prevention, control and treatment of conditions requiring modulation of inflammation in mammals. In another aspect, the present invention relates to the use of compounds of the formula (I) as active ingredients in the manufacture of medicaments/compositions for the prevention, control and treatment of conditions requiring modulation of inflammation. The compounds of formula (I) as defined above may also be useful (for the manufacture of a composition) for the management of pain, fever and injuries, especially sport injuries. Moreover, the compounds of formula (I) as defined above may also be useful (for the manufacture of a composition) for the maintenance and regeneration of articular cartilage.
• Two phthalides from Ligusticum chuangxiong
  作者：Takashi Naito、Takao Katsuhara、Kazuaki Niitsu、Yukinobu Ikeya、Minoru Okada、Hiroshi Mitsuhashi

  DOI：10.1016/0031-9422(92)90051-q

  日期：1992.2

  Two new phthalides, senkyunolides R and S, were isolated from the rhizome of Ligusticum chuanxiong. On the basis of spectral analyses and chemical methods, the structures of senkyunolide R and senkyunolide S were proved to be (6RS,7RS,9SR)-3-butylidene-4,5,6,7-tetrahydro-6,7,9-trihydroxyphthalide and (6RS,7RS,9RS)-3-butylidene-4,5,6,7-tetrahydro-6,7,9-trihydroxyphthalide, respectively.

  从川芎的根茎中分离到了两种新的苯酞，senkyunolides R 和 S。通过光谱分析和化学方法，证明了仙九内酯R和仙九内酯S的结构为(6RS,7RS,9SR)-3-丁叉-4,5,6,7-四氢-6,7,9-三羟基邻苯二甲酸酯和 (6RS,7RS,9RS)-3-丁叉基-4,5,6,7-四氢-6,7,9-三羟基邻苯二甲酸酯，分别。