(-)-tecostidine | 34465-98-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (-)-tecostidine
• 英文别名: [(7S)-7-methyl-6,7-dihydro-5H-cyclopenta[c]pyridin-4-yl]methanol
• CAS: 34465-98-0
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: MZLPWDDUDIIZIR-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-tecostidine 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以61%的产率得到indicain
  参考文献：
  名称：

  Neat total synthesis of six monoterpenic alkaloids of the actinidine series

  摘要：

  A concise enantiopure synthesis of six monoterpenic alkaloids of the actinidine series possessing a cyclopenta[c]lpyridine skeleton, (+)-deoxyrhexifoline (4), (+)-boschniakinic acid (5), (+)-boschniakine (6), (-)-plantagonine (7), (-)-indicaine (8) and (-)-tecostidine (9) is reported starting with the chiral precursor 3 -bromo-5 - ((4R)-phenyloxazolin-2-yl)pyridine (10). It involves a C-4 regioselective connection of a butene appendice and an intramolecular 5-exo-trig Heck annulation sequence followed by hydrogenation of the exocyclic alkene. Mixture of (3R)- and (3S)-7-((4R)-phenyloxazolin-2-yl)cyclopenta[clpyridines was separated by HPLC before being transformed into enantiopure natural products (4-9) by modification of the oxazoline group. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.090
• 作为产物：
  描述：

  甲基(6S,7R)-6-羟基-7-甲基-6,7-二氢-5H-环戊二烯并[d]吡啶-4-羧酸酯 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 15.25h， 生成 (-)-tecostidine
  参考文献：
  名称：

  Ranarivelo, Yvonne; Hotellier, Francoise; Skaltsounis, Alexios-Leandros, Heterocycles, 1990, vol. 31, # 9, p. 1727 - 1731

  摘要：

  DOI：

文献信息

• A rare sesquiterpenoid-alkaloid hydrid with selective BuChE inhibitory activity from Valeriana officinalis var. latifolia Miq
  作者：Miaomiao Wang、Shuliang Wang、Yanan Li、Panfeng Wu、Ping Yi、Liejun Huang、Wei Gu、Chengyan Zhou、Xiaojiang Hao、Chunmao Yuan

  DOI：10.1016/j.tetlet.2022.153679

  日期：2022.3

  as two biosynthetic related compounds (1 and 3) was isolated from the roots of Valeriana officinalis var. latifolia Miq. Compound 2 represented the first germacrane-type sesquiterpenoid and tecostidine hydrid. Their structures as well as absolute configurations were elucidated by spectroscopic analysis, an alkaline hydrolysis method, and X-ray diffraction. The structure of volvalerenic acid A was revised

  Valerianofal A ( 2 ) 是一种稀有的倍半萜类生物碱氢化物，以及两种生物合成相关化合物 ( 1和3 ) 从Valeriana officinalis var.的根中分离得到。阔叶草 化合物2代表第一个germacran-type 倍半萜和 tecostidine hydrad。通过光谱分析、碱解法和 X 射线衍射阐明了它们的结构和绝对构型。通过单晶X射线衍射修正了volvalerenic acid A的结构。化合物2和3显示出选择性 BuChE 抑制活性，IC 50值范围为 0.4 μg/ml 至 2.8 μg/ml。通过分子对接分析预测了化合物2与BuChE之间可能的识别机制。
• Neat total synthesis of six monoterpenic alkaloids of the actinidine series
  作者：Nicolas Robert、Christophe Hoarau、Francis Marsais

  DOI：10.1016/j.tet.2007.02.090

  日期：2007.4

  A concise enantiopure synthesis of six monoterpenic alkaloids of the actinidine series possessing a cyclopenta[c]lpyridine skeleton, (+)-deoxyrhexifoline (4), (+)-boschniakinic acid (5), (+)-boschniakine (6), (-)-plantagonine (7), (-)-indicaine (8) and (-)-tecostidine (9) is reported starting with the chiral precursor 3 -bromo-5 - ((4R)-phenyloxazolin-2-yl)pyridine (10). It involves a C-4 regioselective connection of a butene appendice and an intramolecular 5-exo-trig Heck annulation sequence followed by hydrogenation of the exocyclic alkene. Mixture of (3R)- and (3S)-7-((4R)-phenyloxazolin-2-yl)cyclopenta[clpyridines was separated by HPLC before being transformed into enantiopure natural products (4-9) by modification of the oxazoline group. (C) 2007 Elsevier Ltd. All rights reserved.
• Ranarivelo, Yvonne; Hotellier, Francoise; Skaltsounis, Alexios-Leandros, Heterocycles, 1990, vol. 31, # 9, p. 1727 - 1731
  作者：Ranarivelo, Yvonne、Hotellier, Francoise、Skaltsounis, Alexios-Leandros、Tillequin, Francois

  DOI：——

  日期：——