3-aminooct-2-enoic acid methyl ester | 916520-57-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-aminooct-2-enoic acid methyl ester
• 英文别名: methyl 3-aminooct-2-enoate；methyl (E)-3-aminooct-2-enoate
• CAS: 916520-57-5
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: WOIMICKYEGOIRN-BQYQJAHWSA-N

物化性质

• 沸点：
  266.6±13.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-aminooct-2-enoic acid methyl ester 在 吡啶 、 pyridinium hydrobromide perbromide 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 16.58h， 生成 (+)-trans-9-(3-bromo-4-fluorophenyl)-3-butyl-5,9-dihydro-3H,4H-2,6-dioxa-4-azacyclopenta[b]naphthalene-1,8-dione
  参考文献：
  名称：

  Effects of Substitution on 9-(3-Bromo-4-fluorophenyl)-5,9-dihydro-3H,4H-2,6-dioxa-4- azacyclopenta[b]naphthalene-1,8-dione, a Dihydropyridine ATP-Sensitive Potassium Channel Opener

  摘要：

  Structure-activity relationships were investigated on the tricyclic dihydropyridine ( DHP) K-ATP openers 9-(3-bromo-4-fluorophenyl)-5,9- dihydro-3H, 4H-2,6-dioxa-4-azacyclopenta[ b] naphthalene-1,8-dione ( 6) and 10( 3-bromo-4-fluorophenyl)-9,10-dihydro-1H, 8H-2,7-dioxa-9-azaanthracene-4,5-dione ( 65). Substitution off the core of the DHP, absolute stereochemistry, and aromatic substitution were evaluated for KATP channel activity using Ltk-cells stably transfected with the Kir6.2/SUR2B exon 17- splice variant and in an electrically stimulated pig bladder strip assay. A select group of compounds was evaluated for in vitro inhibition of spontaneous bladder contractions. Several compounds were found to have the unique characteristic of partial efficacy in both the cell-based and electrically stimulated bladder strip assays but full efficacy in inhibiting spontaneous bladder strip contractions. For compound 23b, this profile was mirrored in vivo where it was fully efficacious in inhibiting spontaneous myogenic bladder contractions but only partially able to reduce neurogenically mediated reflex bladder contractions.

  DOI：

  10.1021/jm060549u
• 作为产物：
  描述：

  己酰乙酸甲酯 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 3-aminooct-2-enoic acid methyl ester
  参考文献：
  名称：

  Effects of Substitution on 9-(3-Bromo-4-fluorophenyl)-5,9-dihydro-3H,4H-2,6-dioxa-4- azacyclopenta[b]naphthalene-1,8-dione, a Dihydropyridine ATP-Sensitive Potassium Channel Opener

  摘要：

  Structure-activity relationships were investigated on the tricyclic dihydropyridine ( DHP) K-ATP openers 9-(3-bromo-4-fluorophenyl)-5,9- dihydro-3H, 4H-2,6-dioxa-4-azacyclopenta[ b] naphthalene-1,8-dione ( 6) and 10( 3-bromo-4-fluorophenyl)-9,10-dihydro-1H, 8H-2,7-dioxa-9-azaanthracene-4,5-dione ( 65). Substitution off the core of the DHP, absolute stereochemistry, and aromatic substitution were evaluated for KATP channel activity using Ltk-cells stably transfected with the Kir6.2/SUR2B exon 17- splice variant and in an electrically stimulated pig bladder strip assay. A select group of compounds was evaluated for in vitro inhibition of spontaneous bladder contractions. Several compounds were found to have the unique characteristic of partial efficacy in both the cell-based and electrically stimulated bladder strip assays but full efficacy in inhibiting spontaneous bladder strip contractions. For compound 23b, this profile was mirrored in vivo where it was fully efficacious in inhibiting spontaneous myogenic bladder contractions but only partially able to reduce neurogenically mediated reflex bladder contractions.

  DOI：

  10.1021/jm060549u

文献信息

• A Formal Synthesis of (−)-Perhydrohistrionicotoxin Using a Cross Metathesis–Hydrogenation Approach
  作者：Nicolas D. Spiccia、James Burnley、Kamani Subasinghe、Christopher Perry、Laurent Lefort、W. Roy Jackson、Andrea J. Robinson

  DOI：10.1021/acs.joc.7b01257

  日期：2017.8.18

  development of an efficient, high yielding six-step convergent synthesis of the semisynthetic alkaloid (−)-perhydrohistrionicotoxin is described. The key transformations include the cross metathesis of a Brønsted-acid masked primary homoallylic amine with a vinyl cyclohexenone and a regioselective palladium catalyzed hydrogenation. This sequence generated the advanced Winterfeldt spirocyclic precursor in 47%

  描述了一种高效，高产率的六步收敛聚合半合成生物碱（-）-过氢组蛋白毒素的合成方法。关键的转化包括布朗斯台德酸掩蔽的伯均烯丙基胺与乙烯基环己烯酮的交叉复分解反应和区域选择性钯催化的氢化反应。该序列以47％的总产率产生了先进的温特费尔特螺环前体，具有五个步骤的最长线性序列。