methyl 2-decynoate | 67587-20-6

• 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: methyl 2-decynoate
• 英文别名: Dec-2-insaeure-methylester；Nonin-(1)-carbonsaeure-(1)-methylester；Decin-(2)-saeure-methylester；dec-2-ynoic acid methyl ester；Methyl dec-2-ynoate
• CAS: 67587-20-6
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: UQRQXBZUSCNTDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  115-117 °C(Press: 4 Torr)
• 密度：
  0.925±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  methyl 2-decynoate 在 Lindlar's catalyst 氢气 作用下， 以 苯 为溶剂， 生成 (2Z)-癸烯酸甲酯
  参考文献：
  名称：

  Alder,K.; von Brachel,H., Justus Liebigs Annalen der Chemie, 1962, vol. 651, p. 141 - 153

  摘要：

  DOI：
• 作为产物：
  描述：

  1-壬炔 在 tetrabutylammonium tetrafluoroborate 、 potassium carbonate 、 magnesium 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0~50.0 ℃ 、50.67 kPa 条件下， 反应 15.0h， 生成 methyl 2-decynoate
  参考文献：
  名称：

  摘要：

  DOI：

  10.1002/1099-0690(200107)2001:13<2507::aid-ejoc2507>3.0.co;2-p

文献信息

• Total Synthesis and Configurational Validation of (+)-Violapyrone C
  作者：Jong Seok Lee、Junho Shin、Hee Jae Shin、Hwa-Sun Lee、Yeon-Ju Lee、Hyi-Seung Lee、Hoshik Won

  DOI：10.1002/ejoc.201402524

  日期：2014.7

  of tert-butyl ynoates afforded α-pyrone cores of violapyrones. Moreover, this reaction was successfully applied to the stereospecific syntheses of (+)- and (–)-violapyrone C, which allowed the absolute configuration of natural (+)-violapyrone C to be assigned by comparison of the optical rotations. This first total synthesis, which proceeded in 22 % yield over 10 steps from (S)-(–)-2-methylbutanol, features

  金 (I) 催化的 ynoates 叔丁酯的分子内 6-endo-dig 环化得到 violapyrones 的 α-pyrone 核。此外，该反应成功地应用于 (+)- 和 (-)-violapyrone C 的立体有择合成，这允许通过比较旋光度来分配天然 (+)-violapyrone C 的绝对构型。这是第一次全合成，从 (S)-(-)-2-甲基丁醇以 22% 的产率进行 10 个步骤，具有氧化银 (I) 促进 1,4-丁二醇的单苄基化、Wittig 烯化、克莱森缩合、Corey– Fuchs 反应和金 (I) 催化的 α-吡喃酮合成。
• Transition metal complexes in organic synthesis. Part 65: Iron-mediated synthesis of carazostatin, a free radical scavenger from Streptomyces chromofuscus, and O-methylcarazostatin
  作者：Hans-Joachim Knölker、Thomas Hopfmann

  DOI：10.1016/s0040-4020(02)01180-8

  日期：2002.10

  Highly efficient syntheses of the free radical scavenger carazostatin and its O-methyl derivative are described using cyclohexa-1,3-diene and 2-heptyl-4-methoxy-3-methylaniline as starting materials and iron-mediated oxidative cyclizations as key-steps.

  描述了以环己-1,3-二烯和2-庚基-4-甲氧基-3-甲基苯胺为起始原料并以铁介导的氧化环化为关键步骤的自由基清除剂Carazostatin及其O-甲基衍生物的高效合成方法。
• Cationic Palladium(II)-Catalyzed Highly Enantioselective [3 + 2] Annulation of 2-Acylarylboronic Acids with Substituted Alkynes
  作者：Miao Yang、Xumu Zhang、Xiyan Lu

  DOI：10.1021/ol702503e

  日期：2007.11.1

  [GRAPHICS]A cationic palladium(II)-catalyzed enantioselective tandem [3 + 2] annulation of 2-acylarylboronic acids with substituted alkynes to yield optically active 1-indenols was developed in high yields and excellent enantioselectivities.
• Palladium(II)-Catalyzed Three-Component Coupling Reaction Initiated by Acetoxypalladation of Alkynes:  An Efficient Route to γ,δ-Unsaturated Carbonyls
  作者：Ligang Zhao、Xiyan Lu

  DOI：10.1021/ol026741h

  日期：2002.10.1

  [GRAPHICS]A divalent palladium-catalyzed coupling reaction of electron-deficient alkynes and acrolein or MVK (methyl vinyl ketone) was developed. The reaction provides an efficient method to synthesize gamma,delta-unsaturated carbonyls. A mechanism involving acetoxypalladation of alkyne, followed by insertion of alkene and protonolysis of the C-Pd bond, is proposed. The protonolysis of the carbon-palladium bond with the assistance of bidentate nitrogen containing ligands is the key step in this tandem reaction.
• Stereospecific synthesis of trisubstituted and tetrasubstituted olefins. Conjugate addition of dialkylcopper-lithium reagents to .alpha.,.beta.-acetylenic esters
  作者：Elias J. Corey、John A. Katzenellenbogen

  DOI：10.1021/ja01035a045

  日期：1969.3