5-methylhex-1-en-3-yl acetate | 20726-53-8

• 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: 5-methylhex-1-en-3-yl acetate
• CAS: 20726-53-8
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: VFNIMSPTRLISBK-UHFFFAOYSA-N

物化性质

• 沸点：
  60-62 °C(Press: 12 Torr)
• 密度：
  0.885±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  5-methylhex-1-en-3-yl acetate 在 双(乙腈)氯化钯(II) 作用下， 以 四氢呋喃 为溶剂， 生成 [(E)-5-methylhex-2-enyl] acetate
  参考文献：
  名称：

  [EN] ESTERS OF 5-METHYLHEX-2-ENOL AND THEIR USE AS AROMA CHEMICALS
  [FR] ESTERS DE 5-MÉTHYLHEX-2-ÉNOL ET LEUR UTILISATION COMME PRODUITS CHIMIQUES AROMATIQUES

  摘要：

  The present invention relates to use of at least one compound of formula (I) or stereoisomer thereof wherein R is linear or branched C1-C9alkyl, linear or branched C2-C9alkenyl, unsubstituted or C1- C3alkyl-substituted C4-C8cycloalkyl or substituted or unsubstituted aryl as aroma ingredient. The at least one compound of formula (I) may be used to impart an aroma impression which is reminiscent of a fruity note, green pear note, apple note, juicy - fruity note, styrax note pineapple note, dusty note, watery note, or a combination of two or more notes to a composition and also to enhance and/or modify the aroma of a composition. The present invention is further directed to a composition comprising at least one compound of formula (I) and (i) at least one aroma chemical different from compound of formula (I) and/or (ii) at least one non-aroma chemical carrier. It is also directed to certain compounds of formula (I) per se and processes of their preparation.

  公开号：

  WO2023052353A1
• 作为产物：
  描述：

  异戊醛 在 吡啶 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.5h， 生成 5-methylhex-1-en-3-yl acetate
  参考文献：
  名称：

  Highly Efficient Kinetic Resolution of Allylic Alcohols with Terminal Double Bond

  摘要：

  在本研究中，采用脂肪酶催化的动力学解析（Novozyme 435）制备了端双键的手性烯丙醇和醋酸酯，恩基异纯度范围为94%至99%。

  DOI：

  10.2174/157017811799304151

文献信息

• Catalytic Asymmetric Synthesis of Chiral Allylic Esters
  作者：Jeffrey S. Cannon、Stefan F. Kirsch、Larry E. Overman

  DOI：10.1021/ja106685w

  日期：2010.11.3

  A broadly useful catalytic enantioselective synthesis of branched allylic esters from prochiral (Z)-2-alkene-1-ols has been developed. The starting allylic alcohol is converted to its trichloroacetimidate intermediate by reaction with trichloroacetonitrile, either in situ or in a separate step, and this intermediate undergoes clean enantioselective S(N)2' substitution with a variety of carboxylic acids

  已经开发了一种广泛有用的催化对映选择性合成从前手性 (Z)-2-烯烃-1-醇的支链烯丙酯。起始烯丙醇通过与三氯乙腈反应，在原位或在单独的步骤中转化为其三氯乙酰亚胺中间体，并且该中间体在钯的存在下用各种羧酸进行干净的对映选择性 S(N)2' 取代（ II)催化剂(R(p),S)-di-μ-乙酰基双[(η(5)-2-(2'-(4'-甲基乙基)恶唑啉基)环戊二烯基-1-C,3'-N)( η(4)-四苯基环丁二烯)钴]二钯，(R(p),S)-[COP-OAc](2)，或其对映异构体。定义了这种有用的催化不对称烯丙基酯化的范围和限制。
• Highly Efficient Kinetic Resolution of Allylic Alcohols with Terminal Double Bond
  作者：Francisco A. Marques、Marcos A. Oliveira、Gustavo Frensch、Beatriz Helena L. N. Sales Maia、Andersson Barison、Cesar A. Lenz、Palimecio G. Guerrero

  DOI：10.2174/157017811799304151

  日期：2011.12.1

  In this study, the lipase-catalyzed kinetic resolution (Novozyme 435) was employed to prepare chiral allylic alcohols and acetates with terminal double bonds in enantiomeric excesses ranging from 94 to 99 %.

  在本研究中，采用脂肪酶催化的动力学解析（Novozyme 435）制备了端双键的手性烯丙醇和醋酸酯，恩基异纯度范围为94%至99%。
• Regioselective Asymmetric Allylic Alkylation Reaction of<b>α</b>-Cyanoacet­ates Catalyzed by a Heterobimetallic Platina-/Palladacycle
  作者：Marcel Weiss、Julia Holz、René Peters

  DOI：10.1002/ejoc.201501290

  日期：2016.1

  describe the use of heterobimetallic PtII/PdII complexes, which probably activate the olefinic substrates through an SN2′ pathway. The reaction of α-cyanoacetates delivers linear allylation products with exclusive regioselectivity and high E/Z-selectivity for the new C=C double bond. Although the enantioselectivities attained are moderate, they are significantly higher than with related mono-PdII or -PtII

  烯丙基取代反应为 CH 酸性亲核试剂的功能化提供了有价值的工具。通常，控制亲核反应物产生的立体中心仍然是一个挑战。解决这个问题的大多数研究采用具有低金属氧化态（例如 Pd0）的金属配合物通过氧化加成形成烯丙基配合物。在这篇文章中，我们描述了异双金属 PtII/PdII 复合物的使用，它可能通过 SN2' 途径激活烯烃底物。α-氰基乙酸酯的反应产生线性烯丙基化产物，对新的 C=C 双键具有独特的区域选择性和高 E/Z 选择性。尽管获得的对映选择性适中，但它们明显高于相关的单 PdII 或 -PtII 催化剂或相应的双 PdII 复合物，这表明不同金属的合作。对照实验表明同时激活两个反应伙伴。
• Regio‐ and Enantioselective Iridium‐Catalyzed N‐Allylation of Indoles and Related Azoles with Racemic Branched Alkyl‐Substituted Allylic Acetates
  作者：Seung Wook Kim、Tabitha T. Schempp、Jason R. Zbieg、Craig E. Stivala、Michael J. Krische

  DOI：10.1002/anie.201902799

  日期：2019.6.3

  Cyclometallated π‐allyliridium C,O‐benzoates modified with (S)‐tol‐BINAP, which are stable to air, water, and SiO2, catalyze highly enantioselective N‐allylations of indoles and related azoles. This reaction complements previously reported metal‐catalyzed indole allylations in that complete levels of N versus C3 and branched versus linear regioselectivity are observed.

  （S）-tol-BINAP改性的环金属化π-烯丙基铱C，O-苯甲酸酯对空气，水和SiO 2稳定，可催化吲哚和相关唑类的高度对映选择性N-烯丙基化。该反应是对先前报道的金属催化的吲哚烯丙基化反应的补充，可以观察到N相对于C3的完全水平以及支链相对于线性区域选择性的完整水平。
• Nickel/Photo-Cocatalyzed C(sp²)–H Allylation of Aldehydes and Formamides
  作者：Pei Fan、Rui Wang、Chuan Wang

  DOI：10.1021/acs.orglett.1c02938

  日期：2021.10.1

  nickel/photo-cocatalyzed C(sp2)–H allylation of aldehydes and formamides wherein both allyl acetates and allyl alcohols can be used as the allylating agents. In this reaction, radical-type umpolung of the formyl moiety is enabled by tetrabutylammonium decatungstate as a hydrogen-atom-transfer photocatalyst, whereas nickel serves to cleave the C–O bond of allyl acetates or allyl alcohols. The synergistic effect

  在此，我们报告了一种镍/光共催化的醛和甲酰胺的C(sp 2 )-H 烯丙基化，其中乙酸烯丙酯和烯丙醇均可用作烯丙基化剂。在该反应中，四丁基十钨酸铵作为氢原子转移光催化剂实现了甲酰基部分的自由基型聚合，而镍则用于裂解乙酸烯丙酯或烯丙醇的 C-O 键。这两种催化剂的协同作用为获得各种具有高选择性的 β,γ-不饱和酮和酰胺提供了新的途径。