2-tetradecenoic acid ethyl ester | 165601-77-4

• 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: 2-tetradecenoic acid ethyl ester
• 英文别名: ethyl (2E)-pentadec-2-enoate；(2E)-Ethyl 2-pentadecenoate；(E)-ethyl pentadec-2-enoate；ethyl (E)-pentadec-2-enoate；ethyl (2E)-pentadecenoate
• CAS: 165601-77-4
• 化学式: C₁₇H₃₂O₂
• 分子量: 268.44
• InChiKey: MXMABNZXUFMCGS-FOCLMDBBSA-N

物化性质

• 沸点：
  341.4±11.0 °C(Predicted)
• 密度：
  0.876±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  2-tetradecenoic acid ethyl ester 在 palladium on activated charcoal 、 potassium carbonate 、 potassium hexacyanoferrate(III) manganese(IV) oxide 、 四氧化锇 、 Hydroquinone 1,4-phthalazinediyl diether 、 18-冠醚-6 、 甲基磺酰胺 、 potassium tert-butylate 、 氢气 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 叔丁醇 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 51.0h， 生成 (+)-muricatacin
  参考文献：
  名称：

  De Novo Asymmetric Syntheses of Muricatacin and Its Analogues via Dihydroxylation of Dienoates

  摘要：

  A short and highly efficient route to both enantiomers of muricatacin as well as the C-5-epimer has been developed. The key to the overall transformation is the highly regio- and enantioselective Sharpless asymmetric dihydroxylation of an (E,Z)-dienoate. The highly efficient stereoselective synthesis prepares (-)-muricatacin in seven steps and 66% overall yield.

  DOI：

  10.1021/jo061057s
• 作为产物：
  描述：

  十三酸 在 正丁基锂 、 草酰氯 、 二异丁基氢化铝 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 23.25h， 生成 2-tetradecenoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of 6-Hydroxysphingosine and α-Hydroxy Ceramide Using a Cross-Metathesis Strategy

  摘要：

  In this paper, a new synthetic route toward 6-hydroxysphingosine and alpha-hydroxy ceramide is described. The synthesis employs a cross-metathesis to unite a sphingosine head allylic alcohol with a long-chain fatty acid alkene that also bears an allylic alcohol group. To allow for a productive CM coupling, the sphingosine head allylic alcohol was protected with a cyclic carbonate moiety and a reactive CM catalyst system, consisting of Grubbs II catalyst and CuI, was employed.

  DOI：

  10.1021/acs.joc.5b00823

文献信息

• Isolation and Asymmetric Total Synthesis of Fungal Secondary Metabolite Hygrophorone B¹²
  作者：Eileen Bette、Alexander Otto、Tobias Dräger、Kurt Merzweiler、Norbert Arnold、Ludger Wessjohann、Bernhard Westermann

  DOI：10.1002/ejoc.201403455

  日期：2015.4

  has been isolated and subsquently synthesized in enantiomerically pure form. The total synthesis includes a Sharpless asymmetric dihydroxylation protocol as the stereodifferentiating step, followed by two diastereoselective aldol-type reactions. The approach allows the unambiguous control of all three stereogenic centres, and, furthermore, unequivocal determination of the relative and absolute configuration

  Hygrophorone B12 是来自 Hygrophorus abieticola 子实体的一种新的抗真菌成分，已被分离出来并随后以对映体纯的形式合成。全合成包括 Sharpless 不对称二羟基化方案作为立体分化步骤，然后是两个非对映选择性羟醛型反应。该方法允许对所有三个立体中心进行明确控制，此外，首次明确确定抗生素 hygrophorone B 的相对和绝对构型。
• First Asymmetric Synthesis of 6-Hydroxy-4-Sphingenine-Containing Ceramides. Use of Chiral Propargylic Alcohols To Prepare a Lipid Found in Human Skin
  作者：Jiong Chun、Hoe-Sup Byun、Robert Bittman

  DOI：10.1021/jo026240+

  日期：2003.1.1

  present here the first synthesis of the 6S and 6R diastereoisomers 2 and 3, which represent analogues of (2S,3R)-ceramide (1) having two allylic hydroxyl groups. Chiral propargylic alcohols 8 and 11, which were prepared by asymmetric dihydroxylation of alpha,beta-unsaturated ester 13 and allylic chloride 22, respectively, were employed as precursors of 2 and 3. Nucleophilic addition of lithiated TBS-protected

  最近在人的皮肤中发现了含6-羟基-（4E）-鞘氨醇的神经酰胺。我们在这里介绍了6S和6R非对映异构体2和3的首次合成，它们代表具有两个烯丙基羟基的（2S，3R）-神经酰胺（1）的类似物。分别通过α，β-不饱和酯13和烯丙基氯化物22的不对称二羟基化制备的手性炔丙醇8和11分别用作2和3的前体。 1-丝氨酸衍生的醛26分别提供恶唑烷中间体27和33.酸介导的恶唑烷脱保护，然后N-酰化和桦木还原，完成2和3的合成。
• Stereospecific route to enantiopure all cis-2,3,6-trisubstituted piperidines. Facile synthesis of (−)-deoxocassine and (+)-azimic acid
  作者：Dawei Ma、Nan Ma

  DOI：10.1016/s0040-4039(03)00820-7

  日期：2003.5

  of the enantiopure β-amino esters 10 provides the γ-amnio alcohol 11, which is condensed with 2,4-pentadione to afford 12. Stepwise cyclization of 12 produced the cyclic enamine 13, which is hydrogenated to deliver all cis-2,3,6-trisubstituted piperidine 14. Using this reaction sequence and subsequent Baeyer–Villiger oxidation as the key step (−)-deoxocassine and (+)-azimic acid are synthesized.

  对映体纯的β-氨基酯10的还原提供了γ-氨醇11，将其与2,4-戊二酮缩合得到12。12的逐步环化产生环状烯胺13，其被氢化以递送所有顺式-2,3,6-三取代哌啶14。使用该反应顺序和随后的Baeyer-Villiger氧化作为关键步骤，可以合成（-）-脱氧卡西汀和（+）-叠氮酸。
• Diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid
  作者：Rodney A. Fernandes、Mahesh B. Halle、Asim K. Chowdhury、Arun B. Ingle

  DOI：10.1016/j.tetasy.2011.12.012

  日期：2012.1

  A diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid, common members of the paraconic acids is described. The synthesis is based on a diastereoselective orthoester Johnson-Claisen rearrangement of a (Z)-allyl alcohol with a vicinal dioxolane moiety as key steps. The synthesis is completed in 10 steps and with overall yields of 15.9% for (+)-nephrosterinic acid and 16.4% for (+)-protolichesterinic acid. (C) 2012 Elsevier Ltd. All rights reserved.
• C-1 Reactivity of 2,3-Epoxy Alcohols via Oxirane Opening with Metal Halides: Applications and Synthesis of Naturally Occurring 2,3-Octanediol, Muricatacin, 3-Octanol, and 4-Dodecanolide
  作者：Carlo Bonini、Chiara Federici、Leucio Rossi、Giuliana Righi

  DOI：10.1021/jo00120a025

  日期：1995.7

  The C-1 reactivity of 2,3-epoxy alcohols and derivatives has been examined thoroughly. In the first approach a rearrangement opening of 2,3-epoxy alcohols with LiI leads to 1-iodo 2,3-diols with erythro or three stereochemistry starting from trans or cis epoxy alcohols. Subsequent coupling with a carbon nucleophile can lead to a series of vicinal diols with predicted relative and absolute stereochemistry: the described methodology has been applied to the asymmetric synthesis of the naturally occurring (S,S)-2,3-octanediol and (R,R)-muricatacin. The second approach, starting from easily available tosyloxy epoxides, leads to the highly regioselective opening of the oxirane ring with Li halides. The 3-iodohydrins obtained can be reduced to the corresponding 1-(tosyloxy)alkan-2-ols and then coupled with common carbon nucleophiles to afford, in high yields, optically active alcohols. This methodology has been applied to the asymmetric synthesis of naturally occurring pheromones like 3(R)-octanol and 4(R)-dodecanolide.