(E)-2-(hex-2-en-1-yloxy)acetic acid | 175019-14-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-2-(hex-2-en-1-yloxy)acetic acid
• 英文别名: 2-[(2E)-2-Hexen-1-yloxy]acetic acid；2-[(E)-hex-2-enoxy]acetic acid
• CAS: 175019-14-4
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: LZDGPOYGMJEHJA-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  11.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-2-(hex-2-en-1-yloxy)acetic acid 在 4-二甲氨基吡啶 N,N'-二环己基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 2-[(E)-hex-2-enoxy]-3-hydroxy-3-methylbutanoate
  参考文献：
  名称：

  The Dienolate [2,3]-Wittig Rearrangement – Diastereoselective Synthesis of Highly Functionalized Tertiary Alcohols

  摘要：

  DOI：

  10.1002/(sici)1099-0690(199911)1999:11<2713::aid-ejoc2713>3.0.co;2-e
• 作为产物：
  描述：

  反式-2-已烯-1-醇 、 溴乙酸 在 sodium hydride 作用下， 生成 (E)-2-(hex-2-en-1-yloxy)acetic acid
  参考文献：
  名称：

  手性α-烯丙氧基-的不对称[2,3] -sigmatropic wittig重排

  摘要：

  不对称[2,3] -Wittig手性α烯丙氧基腙（重排小号）-3和（小号）-7具有非常良好的产率继续进行（72 - 100％）以高一起顺-selectivities（87 - 97％的）和不对称感应（63-92％）得到相应的α-羟基hydr 4和8。根据原料的取代方式，可以高对映体过量（92 – 98％）和顺选择性（88 – > 99％）色谱纯化并除去辅助剂后。

  DOI：

  10.1016/0040-4020(95)00982-5

文献信息

• <i>N</i>-aryl 2-aryloxyacetamides as a new class of fatty acid amide hydrolase (FAAH) inhibitors
  作者：Naresh Sunduru、Mona Svensson、Mariateresa Cipriano、Sania Marwaha、C. David Andersson、Richard Svensson、Christopher J. Fowler、Mikael Elofsson

  DOI：10.1080/14756366.2016.1265520

  日期：2017.1.1

  Fatty acid amide hydrolase (FAAH) is a promising target for the development of drugs to treat neurological diseases. In search of new FAAH inhibitors, we identified 2-(4-cyclohexylphenoxy)-N-(3-(oxazolo[4,5-b]pyridin-2-yl)phenyl)acetamide, 4g, with an IC50 of 2.6 µM as a chemical starting point for the development of potent FAAH inhibitors. Preliminary hit-to-lead optimisation resulted in 2-(4-phe

  脂肪酸酰胺水解酶（FAAH）是开发用于治疗神经系统疾病的药物的有希望的目标。为了寻找新的FAAH抑制剂，我们确定了2g 2-（4-环己基苯氧基）-N-（3-（恶唑并[4,5-b]吡啶-2-基）苯基）乙酰胺，IC50为2.6 µM，开发有效的FAAH抑制剂的化学起点。初步的逐线优化得到2-i-（4-phenylphenoxy）-N-（3-（oxazolo [4,5-b] pyridin-2-yl）phenyl）乙酰胺4i，IC50为0.35 µM。
• Electrochemical methoxymethylation of alcohols – a new, green and safe approach for the preparation of MOM ethers and other acetals
  作者：Xiya Luo、Xiaofeng Ma、Frédéric Lebreux、István E. Markó、Kevin Lam

  DOI：10.1039/c8cc05843a

  日期：——

  A new, green, safe, cost-effective and highly efficient electrochemical approach for the methoxymethylation of alcohols and phenols was successfully developed. The methodology was also applied to the synthesis of substituted acetals.

  成功开发了一种新的，绿色的，安全的，具有成本效益的和高效的电化学方法，用于醇和酚的甲氧基甲基化。该方法还用于取代乙缩醛的合成。
• Concise stereoselective synthesis of cis-3-alkoxy-2-carbomethoxy medium-ring oxacycles from (R)-3-(3-butenyl)-4-propynoyloxazolidin-2-one
  作者：Daisuke Sato、Kenshu Fujiwara、Hidetoshi Kawai、Takanori Suzuki

  DOI：10.1016/j.tetlet.2007.12.111

  日期：2008.2

  A concise process for the stereoselective synthesis of chiral cis-3-alkoxy-2-carbomethoxy medium-ring oxacycles from (R)-3-(3-butenyl)-4-propynoyloxazolidin-2-one (1) was developed. The process includes five major steps: (i) hetero-Michael reaction between an alcohol and 1, (ii) stereoselective reduction of the resulting ketone, featuring stereochemical assistance of the neighboring oxazolidin-2-one

  开发了一种简明的方法，用于从（R）-3-（3-丁烯基）-4-丙炔基恶唑烷丁二酮（1）立体选择性地合成手性顺式-3-烷氧基-2-羰甲氧基中环氧杂环。该方法包括五个主要步骤：（i）醇与1之间的杂-迈克尔反应，（ii）立体选择性还原生成的酮，其特征在于相邻的恶唑烷二-2-酮基团的立体化学辅助，（iii）用烷氧基酯化乙酸，（iv）生成的手性转移的爱尔兰–克莱森重排，生成3-烷氧基烯丙基乙醇酸酯，以提供顺式-2，3-二烷氧基羧酸酯，和（v）中继闭环烯烃复分解反应以形成中环醚，同时除去恶唑烷-2-酮部分。
• Synthesis of α-Allyloxy-Substituted α,β-Unsaturated Esters via Aldol Condensation. Convenient Access of Highly Substituted Allyl Vinyl Ethers
  作者：Martin Hiersemann

  DOI：10.1055/s-2000-6424

  日期：——

  α-Allyloxy-substituted α,β-unsaturated esters 1a - r have been prepared in 5 steps from commercially available starting materials. The key sequence of the synthesis is an aldol addition between an α-allyloxy-substituted ester 2a - i and an aldehyde R1CHO followed by mesylation and DBU mediated elimination to afford the 2-alkoxycarbonyl-substituted allyl vinyl esters 1a - r. The E/Z ratio of the newly generated vinyl ether double bond is apparently determined by the steric bulk of the vinyl ether double bond substituent R1. Z:E ratios from 3:2-9:1 were obtained.

  δ-烯丙氧基取代的δ，δ-²-不饱和酯 1a - r 是由市场上可买到的起始原料通过 5 个步骤制备而成的。合成的关键步骤是在δ-烯丙氧基取代酯 2a - i 和醛 R1CHO 之间进行醛醇加成，然后进行甲磺化和 DBU 介导的消去反应，得到 2-烷氧基羰基取代的烯丙基乙烯基酯 1a - r。Z:E 比率为 3:2-9:1。
• Palladium(II)-Catalyzed Cycloisomerization of Functionalized 1,5-Hexadienes
  作者：Björn Nelson、Wolf Hiller、Annett Pollex、Martin Hiersemann

  DOI：10.1021/ol201795w

  日期：2011.8.19

  Scope and limitations of the Pd(II)-catalyzed cycloisomerization of functionalized 1,5-hexadienes have been studied. In situ NMR experiments indicate a challenging competition between various reaction pathways. A careful balance between substrate structure, nature of the precatalyst, and reaction conditions was required to gain access to a useful building block for sesquiterpene total synthesis.