methyl trans/cis-2-dodecanoate | 22104-72-9

• 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 trans/cis-2-dodecanoate
• 英文别名: methyl dodec-2-enoate；2-Dodecensaeuremethylester；2-Dodecenoic acid methylester
• CAS: 22104-72-9
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: YWSDDOFJTUOVMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 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 trans/cis-2-dodecanoate 在 copper(l) iodide 、 水 、 sodium hydroxide 作用下， 以 乙醚 、 异丙醇 为溶剂， 反应 4.0h， 生成 3-甲基-十二烷酸
  参考文献：
  名称：

  Cylindrocyclophane Biosynthesis Involves Functionalization of an Unactivated Carbon Center

  摘要：

  The cylindrocyclophanes are a family of natural products that share a remarkable paracyclophane carbon scaffold. Using genome sequencing and bioinformatic analyses; we have discovered a biosynthetic gene cluster involved in the assembly of cylindrocyclophane F. Through a combination of in vitro enzyme characterization and feeding Studies, We Confirm the connection between this gene cluster and cylindrocyclophane production, elucidate the chemical events involved in initiating and terminating an unusual type I polyketide synthase assembly line, and discover that macrocycle assembly involves functionalization of an unactivated carbon center.

  DOI：

  10.1021/ja308318p
• 作为产物：
  描述：

  癸醛 、 甲氧羰基亚甲基三苯基正膦 以 甲苯 为溶剂， 生成 methyl trans/cis-2-dodecanoate
  参考文献：
  名称：

  Synthesis and Antifungal Activity of Rhodopeptin Analogues. 1. Modification of the East and South Amino Acid Moieties

  摘要：

  [GRAPHICS]Structure-activity relationships of the east and south amino acid modified analogues of rhodopeptins, novel antifungal cyclic tetrapeptides isolated from Rhodococcus species Mer-N1033, have been investigated. It was observed that a basic amino acid moiety (lysine or ornithine) as the east amino acid and a hydrophobic and bulky neutral amino acid (i.e., gamma-methylleucine) as the south amino acid were indispensable structure motifs for antifungal activity of rhodopeptin analogues.

  DOI：

  10.1021/ol005631c
• 作为试剂：
  描述：

  N-methoxy-N-methylcinnamamide 在 methyl trans/cis-2-dodecanoate 、 三氟甲磺酸三甲基硅酯 、 三乙基膦 、 二异丁基氢化铝 、 四丁基氟化铵 作用下， 以 甲苯 、 正己烷 、 四氢呋喃 为溶剂， 反应 5.5h， 以92%的产率得到反式肉桂醛
  参考文献：
  名称：

  存在α，β-不饱和酯的情况下对α，β-不饱和Weinreb酰胺的选择性还原

  摘要：

  使用PEt3和三甲基甲硅烷基三氟甲磺酸酯（TMSOTf）在甲苯中回流下，在α，β-不饱和Weinreb酰胺存在下，对α，β-不饱和酯进行选择性原位保护。将混合物的二异丁基氢化铝（DIBAL-H）还原，然后用四正丁基氟化铵（TBAF）处理，可以得到高产率的α，β-不饱和醛以及回收的α，β-不饱和酯。

  DOI：

  10.1248/cpb.c20-00545

文献信息

• <i>cis</i>-Dihydroxylation of Alkenes with Oxone Catalyzed by Iron Complexes of a Macrocyclic Tetraaza Ligand and Reaction Mechanism by ESI-MS Spectrometry and DFT Calculations
  作者：Toby Wai-Shan Chow、Ella Lai-Ming Wong、Zhen Guo、Yungen Liu、Jie-Sheng Huang、Chi-Ming Che

  DOI：10.1021/ja100967g

  日期：2010.9.29

  [Fe(III)(L-N(4)Me(2))Cl(2)](+) (1, L-N(4)Me(2) = N,N'-dimethyl-2,11-diaza[3.3](2,6)pyridinophane) is an active catalyst for cis-dihydroxylation of various types of alkenes with oxone at room temperature using limiting amounts of alkene substrates. In the presence of 0.7 or 3.5 mol % of 1, reactions of electron-rich alkenes, including cyclooctene, styrenes, and linear alkenes, with oxone (2 equiv) for

  [Fe(III)(LN(4)Me(2))Cl(2)](+) (1, LN(4)Me(2) = N,N'-二甲基-2,11-二氮杂[3.3] (2,6)pyridinophane) 是一种活性催化剂，用于在室温下使用有限量的烯烃底物将各种类型的烯烃与 oxone 进行顺式二羟基化。在 0.7 或 3.5 mol % 的 1 存在下，富电子烯烃（包括环辛烯、苯乙烯和线性烯烃）与 oxone（2 当量）反应 5 分钟导致高达 >99% 的底物转化率并提供顺式二醇产品的产率高达 67%，顺式二醇/环氧化物摩尔比高达 16.8:1。对于缺电子烯烃，包括 α,β-不饱和酯和 α,β-不饱和酮，它们与 oxone（2 当量）在 1（3.5 mol%）催化下反应 5 分钟，得到顺式二醇，产率高达 99%高达 >99% 的底物转化率。肉桂酸甲酯 (9.7 g) 与 oxone (1 当量) 的大规模顺式二羟基化得到顺式二醇产物
• Room-temperature Pd-catalyzed methoxycarbonylation of terminal alkynes with high branched selectivity enabled by bisphosphine-picolinamide ligand
  作者：Ding Liu、Miaolin Ke、Tong Ru、Yingtang Ning、Fen-Er Chen

  DOI：10.1039/d1cc06098h

  日期：——

  The challenging room temperature Pd-catalyzed methoxycarbonylation for a wide array of alkynes with excellent branched selectivity has been developed.

  已开发出具有出色支链选择性的广泛烯烃室温Pd催化的甲氧羰基化反应。
• Radical Nature of Pathways to Alkene and Ester from Thermal Decomposition of Primary Alkyl Diacyl Peroxide
  作者：Lev R. Ryzhkov

  DOI：10.1021/jo9512766

  日期：1996.1.1

  Thermal decomposition of a primary alkyl diacyl peroxide 2 is investigated. Dependence of product yields on temperature, viscosity, and solvent polarity is examined in a variety of media. The excess of the alkene disproportionation product 4 and the presence of ester 3 and acid 5 is argued to demonstrate the existence of a discrete acyloxy-alkyl geminate radical pair. Stereoselective deuterium labeling

  研究了伯烷基二酰基过氧化物2的热分解。在多种介质中检查产物产率对温度，粘度和溶剂极性的依赖性。据认为，过量的烯烃歧化产物4以及酯3和酸5的存在证明存在离散的酰氧基-烷基双氨基自由基对。2的立体选择性氘标记以及随后的4的同位素异构体的（1）H-NMR分析证实了检测到的分解产物的自由基性质。
• [EN] INHIBITORS OF YEAST FILAMENTOUS GROWTH AND METHOD OF THEIR MANUFACTURE<br/>[FR] INHIBITEURS DE LA CROISSANCE FILAMENTEUSE DE LA LEVURE ET PROCEDE DE FABRICATION
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2005034933A1

  公开（公告）日：2005-04-21

  The invention broadly relates to the use of α, β-unsaturated fatty acids to inhibit the filamentous growth of fungi and yeasts and to a method for producing same. In particular the invention relates to the use of optionally substituted C8 to C15 α, β-unsaturated fatty acids or salts, esters or amides thereof for inhibiting or retarding the yeast-to-mycelium transition of organisms having a dimorphic life cycle.

  本发明广泛涉及使用α，β-不饱和脂肪酸来抑制真菌和酵母的丝状生长，并提供一种生产它们的方法。特别地，本发明涉及使用选择性取代的C8至C15α，β-不饱和脂肪酸或其盐、酯或酰胺来抑制或延缓具有二态生命周期的生物的酵母菌丝转化。
• Process for the production of keto-diesters
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0334455A1

  公开（公告）日：1989-09-27

  Process for the preparation of keto-diesters which comprises reacting an alkyl ester of a 2-alkenoic acid and an aldehyde in the presence of a catalyst, wherein an aldehyde having two formylic hydrogen atoms is reacted in liquid phase solution with the ester.

  制备酮二酯的工艺，包括在催化剂存在下使 2-烯酸的烷基酯和醛反应，其中具有两个甲酰氢原子的醛在液相溶液中与酯反应。

表征谱图