(+/-)-4-oxo-1-(2-propenyl)-2-cyclohexene-1-methanol | 436145-96-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-4-oxo-1-(2-propenyl)-2-cyclohexene-1-methanol
• 英文别名: 4-allyl-4-(hydroxymethyl)cyclohex-2-en-1-one；4-(Hydroxymethyl)-4-prop-2-enylcyclohex-2-en-1-one
• CAS: 436145-96-9
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: COYAGMBVBKHXAE-UHFFFAOYSA-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：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-4-oxo-1-(2-propenyl)-2-cyclohexene-1-methanol 在 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 4-Allyl-4-methoxymethoxymethyl-6-methyl-cyclohex-2-enone
  参考文献：
  名称：

  Some Aspects of Palladium-Catalyzed Cycloalkenylation:  Developments of Environmentally Benign Catalytic Conditions and Demonstration of Tandem Cycloalkenylation

  摘要：

  The influences of catalysts, substituent groups, and solvents on the palladium-catalyzed cycloalkenylation of cross-conjugated silyl enol ethers of 2-tert-butyldimethylsiloxy-5-(2-propenyl)-1,3-cyclohexadiene derivatives have been investigated. The catalytic reaction proceeded smoothly, even in aqueous media. The product ratios were influenced by the structure of substrates as well as solvents. In addition, it was found that the reaction is applicable to a tandem cyclization for the construction of cedrane skeleton.

  DOI：

  10.1021/jo011169d
• 作为产物：
  描述：

  6-allyl-3-isobutoxy-2-cyclohexen-1-one 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (+/-)-4-oxo-1-(2-propenyl)-2-cyclohexene-1-methanol
  参考文献：
  名称：

  使用钯催化的环烯基化和分子内Diels-Alder反应，对DNA聚合酶α抑制剂蚜虫蛋白进行非对映选择性正式合成。

  摘要：

  [结构：见正文]通过利用钯催化的环烯基化工艺制备的双环[3.2.1]辛烷的独特特性，实现了一种新型的非对映选择性的蚜虫二烯合成。

  DOI：

  10.1021/ol034027+

文献信息

• Total Syntheses of (±)-Platencin and (−)-Platencin
  作者：K. C. Nicolaou、G. Scott Tria、David J. Edmonds、Moumita Kar

  DOI：10.1021/ja906801g

  日期：2009.11.4

  The secondary metabolites platensimycin and platencin, isolated from the bacterial strain Streptomyces platensis, represent a novel class of natural products exhibiting unique and potent antibacterial activity. Platencin, though structurally similar to platensimycin, has been found to operate through a slightly different mechanism of action involving the dual inhibition of lipid elongation enzymes

  从细菌菌株钝顶链霉菌中分离出的次生代谢物钝顶霉素和钝顶霉素代表了一类新型天然产物，具有独特而有效的抗菌活性。Platencin 虽然在结构上与 Platensimycin 相似，但已发现其作用机制略有不同，涉及脂质延伸酶 FabF 和 FabH 的双重抑制。这两种天然产物对主要抗生素耐药菌株（包括耐甲氧西林金黄色葡萄球菌、耐万古霉素金黄色葡萄球菌和耐万古霉素屎肠球菌）均表现出强效、广谱、革兰氏阳性抗菌活性。本文描述了我们对血小板素的合成努力，最终得到了天然产物的外消旋和不对称制备。该合成证明了钴催化的不对称狄尔斯-阿尔德反应和[3.2.1]双环酮一锅还原重排为[2.2.2]双环烯烃的能力。
• Recombination of diterpenoid structure units: Synthesis of antitumor amides bearing functionalized bicyclo[3.2.1]octane ring
  作者：Zewei Mao、Yan Li、Jingbo Chen、Yuanyuan Wang、Hongbin Zhang

  DOI：10.1016/j.bmcl.2010.05.075

  日期：2010.7

  In this work, 23 new amides (14–36) bearing a representative diterpenoid structure unit, the functionalized bicyclo[3.2.1]octane ring, have been synthesized and its antitumor potential is studied. In vitro studies demonstrate that a number of amides with the bicyclo[3.2.1]oct-3-en-2-one subunit are active against HL-60, SMMC-7721, A-549, SK-BR-3, and PANC-1 tumor cell lines. The hybrid derivative,

  在这项工作中，23个新的酰胺（14 - 36）的轴承的代表性二萜结构单元，官能双环[3.2.1]辛烷环，已被合成和其抗肿瘤潜力进行了研究。体外研究表明，具有双环[3.2.1] oct-3-en-2-one亚基的许多酰胺类药物对HL-60，SMMC-7721，A-549，SK-BR-3和PANC具有活性-1肿瘤细胞系。发现杂化衍生物化合物20是最有效的化合物（ 针对HL-60的IC 50 = 1.05μM），并且比阳性对照顺铂（DDP）更有活性。此外，化合物20的IC 50表现出广谱的体外抗癌活性 对五种测试的癌细胞系的1.1-4.3μM值。
• Formal Total Synthesis of Platencin
  作者：Georgy N. Varseev、Martin E. Maier

  DOI：10.1002/anie.200900447

  日期：2009.5.4

  The right bicycle: A concise formal synthesis of platencin was based on an efficient oxygen‐mediated palladium‐catalyzed cycloalkenylation of 1 to form a bicyclo[3.2.1]octane, and a deoxygenative rearrangement of tosylhydrazone 2 to construct the bicyclo[2.2.2]octane 3. The total yield of the core structure 4 of platencin was 17.5 % for 13 steps from a commercially available compound. Ts=p‐toluenesulfonyl

  正确的自行车：基于有效的氧介导的钯催化的环烯基化1形成双环[3.2.1]辛烷，以及甲苯磺酰2 2的脱氧重排以构建双环[2.2.2 ]，简洁而正式地合成了Platencin。]辛烷3。从市售化合物获得的13个步骤中，稿台素核心结构4的总产率为17.5％。Ts =对甲苯磺酰基，TBS =叔丁基二甲基甲硅烷基，Piv =新戊酰基。
• Diastereoselective Formal Total Synthesis of the DNA Polymerase α Inhibitor, Aphidicolin, Using Palladium-Catalyzed Cycloalkenylation and Intramolecular Diels−Alder Reactions
  作者：Masahiro Toyota、Masato Sasaki、Masataka Ihara

  DOI：10.1021/ol034027+

  日期：2003.4.1

  [structure: see text] A novel diastereoselective formal synthesis of aphidicolin has been achieved by exploiting a unique characteristic of a bicyclo[3.2.1]octane prepared by employing a palladium-catalyzed cycloalkenylation process.

  [结构：见正文]通过利用钯催化的环烯基化工艺制备的双环[3.2.1]辛烷的独特特性，实现了一种新型的非对映选择性的蚜虫二烯合成。
• Some Aspects of Palladium-Catalyzed Cycloalkenylation:  Developments of Environmentally Benign Catalytic Conditions and Demonstration of Tandem Cycloalkenylation
  作者：Masahiro Toyota、Marcellino Rudyanto、Masataka Ihara

  DOI：10.1021/jo011169d

  日期：2002.5.1

  The influences of catalysts, substituent groups, and solvents on the palladium-catalyzed cycloalkenylation of cross-conjugated silyl enol ethers of 2-tert-butyldimethylsiloxy-5-(2-propenyl)-1,3-cyclohexadiene derivatives have been investigated. The catalytic reaction proceeded smoothly, even in aqueous media. The product ratios were influenced by the structure of substrates as well as solvents. In addition, it was found that the reaction is applicable to a tandem cyclization for the construction of cedrane skeleton.