Ethyl tridec-2-ynoate | 136616-81-4

• 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: Ethyl tridec-2-ynoate
• CAS: 136616-81-4
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: SQSYKDWFISAXQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Ethyl tridec-2-ynoate 在 silver trifluoromethanesulfonate 、 对甲苯磺酸 作用下， 生成 3-氧代十三酸乙酯
  参考文献：
  名称：

  银(I)盐催化醇立体选择性加成乙炔羧酸酯

  摘要：

  银 (I) 盐在温和条件下平稳地催化醇立体选择性反式加成到乙炔二甲酸二甲酯，以定量收率提供甲氧基富马酸二甲酯。

  DOI：

  10.1246/cl.1996.727
• 作为产物：
  描述：

  1-十二炔 、 氯甲酸乙酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 Ethyl tridec-2-ynoate
  参考文献：
  名称：

  Structure-antitumor Activity Relationship of Semi-synthetic Spicamycin Derivatives.

  摘要：

  新合成了一系列在分子脂肪酸部分进行了修饰的斯匹卡霉素衍生物，并研究了它们的构效关系。通过对脂肪酸部分进行修饰，将其转化为十四碳二烯酸或十二碳二烯酸类似物，这些衍生物对COL-1人结肠癌异种移植模型的抗肿瘤活性显著优于SPM VIII。

  DOI：

  10.7164/antibiotics.48.1467

文献信息

• Metal-Free<i>meta</i>-Selective Alkyne Oxyarylation with Pyridine<i>N</i>-Oxides: Rapid Assembly of Metyrapone Analogues
  作者：Xiangyu Chen、Stefan A. Ruider、Rolf W. Hartmann、Leticia González、Nuno Maulide

  DOI：10.1002/anie.201607988

  日期：2016.12.5

  An efficient metal‐free oxyarylation of electron‐poor alkynes with pyridine N‐oxides has been developed. This transformation affords meta‐substituted pyridines analogous to the drug metyrapone in high regioselectivities. Density functional theory (DFT) calculations provided important insight into the mechanism. Evaluation of the inhibitory properties revealed the most active CYP11B1 inhibitor of these

  已经开发了一种高效的贫电子炔烃与吡啶N-氧化物的无金属氧合反应。这种转化提供了在药物上具有高区域选择性的，与药物甲吡酮类似的间位取代的吡啶。密度泛函理论（DFT）计算提供了对该机理的重要见解。抑制特性的评估表明，这些衍生物是最活跃的CYP11B1抑制剂，具有类似于甲吡酮的两位数纳摩尔抑制活性。
• Ru-Catalyzed Regioselective Cascade Annulation of Acrylamides with 2-Alkynoates for the Synthesis of Various 6-Oxo Nicotinic Acid Esters
  作者：Dnyaneshwar N. Garad、Santosh B. Mhaske

  DOI：10.1021/acs.joc.8b02783

  日期：2019.2.15

  of acrylamides with 2-alkynoates via aza-Michael/C–H activation sequence for the synthesis of various 6-oxo nicotinic acid esters is described. The regioselectivity of the protocol has been confirmed by performing silver mediated protodecarboxylation of the corresponding 6-oxo nicotinic acid to furnish 2-pyridone. The developed protocol is copper or silver salt-free and uses inexpensive, safe, and

  描述了Ru催化的丙烯酰胺与2-炔酸酯通过氮杂-Michael / CH活化序列合成的6-氧代烟酸酯的区域选择性级联环化反应。通过进行相应的6-氧代烟酸的银介导的原脱羧以提供2-吡啶酮，已经证实了该方案的区域选择性。所开发的方案不含铜或银盐，并使用廉价，安全且对环境无害的基于过氧化物的“氧酮”作为唯一氧化剂。还演示了该协议的氧化还原中性版本。
• Synthesis of Triphenylene Derivatives by Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition: Application to the Synthesis of Highly Fluorescent Triphenylene-Based Long Ladder Molecules
  作者：Koichi Murayama、Yayoi Sawada、Keiichi Noguchi、Ken Tanaka

  DOI：10.1021/jo4008892

  日期：2013.6.21

  The convenient synthesis of substituted triphenylenes and azatriphenylenes has been achieved by the cationic rhodium(I)/H-8-BINAP or BINAP complex-catalyzed [2 + 2 + 2] cycloaddition under mild conditions. Photo-physical properties of representative triphenylenes and azatriphenylenes were examined, which revealed that azatriphenylenes showed higher fluorescence quantum yields than triphenylenes. This method was successfully applied to the synthesis of highly fluorescent triphenylene-based long ladder molecules.
• Reductive dimerization of dialkyl acetylenedicarboxylate catalyzed by [Rh(binap)(MeOH)2]ClO4 in methanol
  作者：Kazuhide Tani、Kazuya Ueda、Kenji Arimitsu、Tsuneaki Yamagata、Yasutaka Kataoka

  DOI：10.1016/s0022-328x(98)00507-5

  日期：1998.6

  Cationic Rh(I) complex [Rh(binap)(MeOH)(2)]ClO4 catalyzes reductive dimerization of dialkyl acetylenedicarboxylates 1 to give 1,2,3,4-tetrakis(alkoxycarbonyl)-1,3-butadienes 2 in methanol selectively. (C) 1998 Elsevier Science S.A. All rights reserved.
• Regioselectivity in the reaction of tantalum-unsymmetrical acetylene complexes with carbonyl compounds. Stereoselective preparation of 1-alkenyl sulfides, .alpha.,.beta.-unsaturated esters, and amides
  作者：Yasutaka Kataoka、Jiro Miyai、Makoto Tezuka、Kazuhiko Takai、Kiitiro Utimoto

  DOI：10.1021/jo00051a023

  日期：1992.12

  Tantalum-alkyne complexes, derived by treatment of alkynes with low-valent tantalum (TaCl5 and zinc), react in situ with carbonyl compounds to give (E)-allylic alcohols stereoselectively. When unsymmetrical acetylenes are employed in the reaction, two regioisomeric allylic alcohols are produced. The regioselectivity of the reaction depends on the steric and electronic effects of the substituents on the acetylenes. For example, treatment of tantalum-alkyne complexes derived from methyl alkynyl sulfides with carbonyl compounds yields (E)-3-hydroxy-1-propenyl methyl sulfides in a regioselective manner. Tantalum-alkyne complexes derived from acetylenic esters react with carbonyl compounds regioselectively at the alpha-position of the esters to give Z-isomers of trisubstituted alpha,beta-unsaturated esters. In contrast, tantalum-alkyne complexes derived from acetylenic amides react with carbonyl compounds predominantly at the beta-position of the amides. The regioselectivity of the reaction between acetylenic amides and aldehydes, however, cannot be explained solely in terms of the steric and electronic effects of the substituents. Strong coordination of the amide group to the tantalum center could also be responsible for the observed selectivity, which is opposite to that observed with tantalum-acetylenic ester complexes.