Ethyl o-(1-oxopentyl)benzoate | 131379-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl o-(1-oxopentyl)benzoate
• 英文别名: ethyl-2-pentanoylbenzoate；2-Pentanoyl-benzoic acid ethyl ester；ethyl 2-pentanoylbenzoate
• CAS: 131379-20-9
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: RXTQOFXFLVSTMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl o-(1-oxopentyl)benzoate 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以78%的产率得到3-丁基-1(3H)-异苯并呋喃酮
  参考文献：
  名称：

  钯催化的环境良性酰化反应

  摘要：

  最近的研究趋势已趋向于开发使用无毒试剂的有效策略。较早报道的过渡金属催化的羰基化涉及有毒的一氧化碳（CO）气体作为羰基化剂或官能团辅助的邻位sp 2C–H活化（即邻位酰化）或通过羰基活化（即通过形成烯胺）进行羰基化。与这些方法相反，在此我们描述了一种环境友好的过程，即[Pd]催化的直接羰基化反应，该反应从简单的可商购的碘代芳烃和醛开始，用于合成多种酮。此外，该方法包括使碘代芳烃与醛直接偶联而不活化羰基，也无需直接进行基团辅助。重要的是，该策略已成功地应用于合成正丁基邻苯二甲酸酯和匹托芬酮。

  DOI：

  10.1021/acs.joc.6b01064
• 作为产物：
  描述：

  2-溴苯甲酸乙酯 、 戊酰氯 生成 Ethyl o-(1-oxopentyl)benzoate
  参考文献：
  名称：

  The direct formation of functionalized alkyl(aryl)zinc halides by oxidative addition of highly reactive zinc with organic halides and their reactions with acid chlorides, .alpha.,.beta.-unsaturated ketones, and allylic, aryl, and vinyl halides

  摘要：

  Highly reactive zinc, prepared by the lithium naphthalenide reduction of ZnCl2, readily undergoes oxidative addition to alkyl, aryl, and vinyl halides under mild conditions to generate the corresponding organozinc compounds in excellent yields. Significantly, the reaction will tolerate a spectrum of functional groups on the organic halides. Accordingly, this approach can now be used to prepare a wide variety of highly functionalized organozinc compounds. In the presence of Cu(I) salts, the organozinc compounds cross-couple with acid chlorides, conjugatively add to alpha,beta-unsaturated ketones, and regioselectively undergo S(N)2' substitution reactions with allylic halides. They also cross-couple with aryl or vinyl halides with Pd(0) catalysts.

  DOI：

  10.1021/jo00004a021

文献信息

• An Additional Coordination Group Leads to Extremely Efficient Chiral Iridium Catalysts for Asymmetric Hydrogenation of Ketones
  作者：Jian-Hua Xie、Xiao-Yan Liu、Jian-Bo Xie、Li-Xin Wang、Qi-Lin Zhou

  DOI：10.1002/anie.201102710

  日期：2011.8.1

  What a turnover! An efficient chiral iridium catalyst that bears a tridentate spiro aminophosphine ligand catalyzes the asymmetric hydrogenation of ketones with excellent enantioselectivities (up to 99.9 % ee) and extremely high turnover numbers (TONs; as high as 4 550 000).

  营业额！带有三齿螺氨基膦配体的高效手性铱催化剂可催化酮的不对称氢化，具有出色的对映选择性（高达99.9％ee）和极高的周转率（TONs；高达455万）。
• Catalytic Enantioselective Synthesis of Chiral Phthalides by Efficient Reductive Cyclization of 2-Acylarylcarboxylates under Aqueous Transfer Hydrogenation Conditions
  作者：Bo Zhang、Ming-Hua Xu、Guo-Qiang Lin

  DOI：10.1021/ol901674k

  日期：2009.10.15

  A new diamine ligand for asymmetric transfer hydrogenation (ATH) was discovered. The reductive cyclization of 2-acylarylcarboxylates was found to proceed highly stereoselectively by the new Ru complex-catalyzed ATH and subsequent in situ lactonization under aqueous conditions. It enables efficient access to a wide variety of 3-substituted phthalides in enantiomerically pure form.

  发现了一种新的用于不对称转移氢化（ATH）的二胺配体。发现2-酰基芳基羧酸盐的还原环化通过新的Ru络合物催化的ATH以及随后在水性条件下的原位内酯化而高度立体选择性地进行。它可以有效地获得对映体纯净形式的各种3-取代的邻苯二甲酸酯。
• Preparation of aryl ketones via Ni-catalyzed Negishi-coupling reactions with acid chlorides
  作者：Seung-Hoi Kim、Reuben D. Rieke

  DOI：10.1016/j.tetlet.2011.01.135

  日期：2011.3

  A Ni-catalyst-catalyzed cross-coupling reaction of organozinc reagents with acid chlorides has been successfully developed. Mild reaction conditions were required to complete the coupling reactions affording the corresponding aryl ketones in good to excellent yields.

  已成功开发了镍催化的有机锌试剂与酰氯的交叉偶联反应。需要温和的反应条件以完成偶联反应，以良好至优异的产率提供相应的芳基酮。
• Palladium-Catalyzed Direct Oxidative Coupling of Iodoarenes with Primary Alcohols Leading to Ketones: Application to the Synthesis of Benzofuranones and Indenones
  作者：Basuli Suchand、Chinnabattigalla Sreenivasulu、Gedu Satyanarayana

  DOI：10.1002/ejoc.201900769

  日期：2019.8.15

  investigated, utilizing readily available primary alcohols as acylating sources. Overall, this oxidative coupling proceeds via three distinct transformations such as oxidation, radical formation, and cross-coupling in one catalytic process. This protocol does not involve the assistance of a directing group or activation of the carbonyl group by any other means. Furthermore, this reaction made use of no

  在本研究中，利用容易获得的伯醇作为酰化源，研究了通过交叉脱氢偶联进行钯催化的直接氧化酰化。总体而言，这种氧化偶联通过三种不同的转化进行，例如氧化、自由基形成和一个催化过程中的交叉偶联。该协议不涉及导向基团的协助或通过任何其他方式激活羰基。此外，该反应没有使用有毒的一氧化碳气体作为羰基化剂；相反，原料伯醇已被用作酰化源。值得注意的是，可以合成苯并呋喃酮和茚酮。该策略也适用于正丁基苯酞、非诺贝特、吡托苯酮和新木脂素的合成。
• US5358546A
  申请人：——

  公开号：US5358546A

  公开（公告）日：1994-10-25