E-Tetradec-2-ene-14-olide | 98330-97-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: E-Tetradec-2-ene-14-olide
• 英文别名: 2-Tetradecen-14-olid；Oxacyclopentadec-3-en-2-one；(3E)-1-oxacyclopentadec-3-en-2-one
• CAS: 98330-97-3
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: SMZGTTZMSNGTHB-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  11-溴-1-十一醇 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三苯基氢化锡 、 N,N'-二环己基碳二亚胺 、 sodium iodide 作用下， 以 乙酸乙酯 、 丙酮 、 苯 为溶剂， 反应 14.0h， 生成 E-Tetradec-2-ene-14-olide
  参考文献：
  名称：

  通过丙酸酯进行自由基大环化。

  摘要：

  丙内酯中的分子内自由基加成为三苯基锡氢化物/ AIBN介导的条件下从其相应的ω-碘烷基-丙酸酯中生成14–16元-α，β-不饱和大环内酯提供了一条新的立体选择路线。尝试合成类似的10-13元内酯的尝试均未成功，导致在自由基中心直接还原而得的无环产物。

  DOI：

  10.1016/0040-4020(92)85015-7

文献信息

• Thieme Chemistry Journal Awardees - Where Are They Now? Stereoselective Synthesis of Z-Configured α,β-Unsaturated Macrocyclic Lactones and Diolides by Intramolecular Julia-Kocienski Olefination
  作者：Paul Blakemore、Heath Giesbrecht、Brian Knight、Nicole Tanguileg、Christopher Emerson

  DOI：10.1055/s-0029-1219185

  日期：2010.2

  acid with either ω-alkenols or α,ω-diols, followed by ozonolysis or Dess―Martin oxidation as appropriate, underwent intramolecular Julia―Kocienski olefination when treated with DBU. Macrocyclic α,β-unsaturated lactones of between 12- and 19-membered ring sizes were formed successfully using this tactic (24―44% yield, Z/E ≥ 3.5:1); however, diolides were selectively produced from precursors intended

  由（苯并噻唑-2-基磺酰基）乙酸与 ω-烯醇或 α,ω-二醇酯化，然后进行臭氧分解或 Dess-Martin 氧化（视情况而定）衍生的 ω-磺醛，在用DBU。使用该策略成功地形成了 12 至 19 元环大小的大环 α,β-不饱和内酯（产率 24-44%，Z/E ≥ 3.5:1）；然而，二内酯是由旨在靶向七至九元环内酯的前体选择性生产的（产率 13-70%，ZZ/ZE ≥ 2:1）。
• PROCESS FOR PREPARING UNSATURATED LACTONES
  申请人：Meijer John

  公开号：US20090306411A1

  公开（公告）日：2009-12-10

  The invention relates to a process for preparing saturated or unsaturated lactones. This process involves reacting a bicyclic compound or a monocyclic compound with hydrogen peroxide in the presence of a first acid having a pK a of 3 or less and a first organic solvent, thereby forming a hydroperoxide. The obtained mixture comprising the hydroperoxide is subsequently metered to a mixture of a second organic solvent and a dissociation-enhancing catalyst, optionally comprising a second organic acid. The invention also pertains to a process of preparing the hydroperoxide.

  本发明涉及一种制备饱和或不饱和内酯的方法。该方法涉及在第一有机溶剂中，在第一酸(pKa小于或等于3)的存在下，将双环化合物或单环化合物与过氧化氢反应，从而形成一个过氧化物。随后，将包含过氧化物的混合物滴加到第二有机溶剂和促进解离的催化剂混合物中，可选地包括第二有机酸。本发明还涉及制备过氧化物的方法。
• Processes for obtaining purified unsaturated macrocyclic compounds
  申请人：Agan Aroma & fine chemicals Ltd.

  公开号：US10844036B2

  公开（公告）日：2020-11-24

  A process of obtaining a purified geometric isomer of an unsaturated macrocyclic compound is disclosed herein. The process is effected by contacting an ion exchange medium comprising silver ions with a mixture comprising at least one geometric isomer of the unsaturated macrocyclic compound, to thereby obtain at least one fraction comprising the purified geometric isomer of the macrocyclic compound. A system configured for performing the process is also disclosed.

  本文公开了一种获得不饱和大环化合物纯化几何异构体的工艺。该工艺通过将包含银离子的离子交换介质与包含至少一种不饱和大环化合物几何异构体的混合物接触，从而获得至少一种包含提纯的大环化合物几何异构体的馏分。此外，还公开了一种配置用于执行该工艺的系统。
• <i>Z</i>-Selective Intramolecular Horner−Wadsworth−Emmons Reaction for the Synthesis of Macrocyclic Lactones
  作者：Kaori Ando、Kenji Narumiya、Hirokazu Takada、Taiji Teruya

  DOI：10.1021/ol100071d

  日期：2010.4.2

  When the substrates (ArO)(2)P(O)CH2CO2-CHO (Ar = Ph, o-t-BuPh) were added to a THF solution containing 3 equiv of NaH at 0 degrees C or NaI-DBU at rt over 1-10 h, the Intramolecular Horner-Wadsworth-Emmons reaction proceeded efficiently to give the 12-18-membered-ring lactones in 69-93% yields with 89-100% Z selectivity. On the other hand, (EtO)(2)P(O)CH2CO2-CHO gave the 13-18-membered-ring lactones in 52-82% yields with 89-99% E selectivity using LiCl-DBU in MeCN or THF.
• [EN] PROCESS FOR PREPARING UNSATURATED LACTONES<br/>[FR] PROCEDE DE PREPARATION DE LACTONES INSATURES
  申请人：SYMRISE GMBH & CO KG

  公开号：WO2005113533A9

  公开（公告）日：2009-09-24