γ-(Iodzinkio)buttersaeureethylester | 104089-17-0

• 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: γ-(Iodzinkio)buttersaeureethylester
• 英文别名: ethyl 4-(iodozincio)butanoate；(4-ethoxy-4-oxobutyl)zinc iodide；3-carboethoxypropylzinc iodide
• CAS: 104089-17-0
• 化学式: C₆H₁₁IO₂Zn
• 分子量: 307.447
• InChiKey: MSAFRVMVDPZHPQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  10.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  γ-(Iodzinkio)buttersaeureethylester 在 chromium dichloride 、 溴 、 三苯基膦 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 3.5h， 生成 ethyl 7-hydroxyhept-5-ynoate
  参考文献：
  名称：

  Preparation of polyfunctional allenic alcohols by the regioselective addition of functionalized propargylic chromium(III) organometallics to carbonyl compounds

  摘要：

  The reaction of propargylic halides 1 (X = Cl, Br) with an aldehyde or ketone (0.67 equiv) in the presence of CrCl2 (2.0 equiv) and LiI (2 equiv, necessary if X = Cl) affords allenic alcohols 3 with excellent regioselectivities (3-6% of the regioisomeric acetylenic alcohol 4 is formed) and in good yields (68-90%). Interestingly, this method allows the generation of highly functionalized intermediate propargylic chromium organometallics contained an ester, cyano, or chloride functionality. The alpha-alkyl-substituted propargylic bromide 10 reacts with benzaldehyde yielding the acetylenic alcohol 11 as a diastereomeric mixture of only one regioisomer (90% yield).

  DOI：

  10.1021/jo00041a006
• 作为产物：
  描述：

  4-碘-丁酸乙酯 在 铜 、 锌 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 γ-(Iodzinkio)buttersaeureethylester
  参考文献：
  名称：

  2-碳乙氧基乙基碘化锌和3-碳乙氧基丙基碘化锌的生成及其在γ-和δ-酮酸酯合成中的应用

  摘要：

  通过相应的碘代酯与Zn-Cu对的反应生成2-羰基乙氧基乙基碘化锌和3-羰基乙氧基丙基碘化锌，并用于钯与酰氯的偶合反应，从而分别定量地提供γ-和δ-酮酸酯。

  DOI：

  10.1016/s0040-4039(01)80887-x

文献信息

• A convenient method for the synthesis of Δ1,6-bicyclo[4.n.0]alken-2-ones
  作者：Norihiko Watanabe、Keiji Tanino、Isao Kuwajima

  DOI：10.1016/s0040-4039(99)01723-2

  日期：1999.11

  A convenient annulation method for the synthesis of bicyclic enones from cycloalkanones was developed. In the presence of a Pd(0) catalyst, enol triflates derived from ethyl 2-oxocycloalkanecarboxylates were treated with 3-(ethoxycarbonyl)propylzinc iodide to afford the corresponding diesters via a cross-coupling reaction. The diesters were easily transformed into Δ1,6-bicyclo[4.n.0]alken-2-ones through

  开发了一种方便的环化方法，由环烷酮合成双环烯酮。在Pd（0）催化剂存在下，将衍生自2-氧代环烷羧酸乙酯的烯醇三氟甲磺酸酯用3-（乙氧羰基）丙基碘化锌处理，通过交叉偶联反应得到相应的二酯。二酯很容易转化为Δ 1,6 -二环[4.n.0]链烯-2-酮通过狄克曼缩合反应然后进行脱羧反应。环合方法也可用于合成相应的环庚烯酮衍生物。
• The Synthesis of 1,4-Diketones via a One-pot Five-component Connecting Reaction Based on Two Acylations of Organozincs Promoted by the Catalysis of a Pd(0) Species
  作者：Motoki Yuguchi、Masao Tokuda、Kazuhiko Orito

  DOI：10.1246/cl.2004.674

  日期：2004.6

  Unsymmetrical 1,4-diketones were produced via a one-pot five-component connecting reaction based on two kinds of Pd(0)-catalyzed acylations of organozincs using acryloyl chloride and TMSCl in an atmosphere of carbon monoxide.

  通过一步五组分串联反应，在碳 monoxide 气氛下，利用两种基于Pd(0)催化的有机锌的酰化反应，即使用丙烯酰氯和TMSCl，合成了非对称1,4-二酮。
• Coupling of gem -difluorinated organozinc reagents with S-electrophiles
  作者：Salavat S. Ashirbaev、Vitalij V. Levin、Marina I. Struchkova、Alexander D. Dilman

  DOI：10.1016/j.jfluchem.2016.07.018

  日期：2016.11

  gem-Difluorinated organozinc reagents, which were prepared by insertion of CF2-fragment into CZn bond, couple with diethyl dixanthogen, di(benzothiazolyl) disulfide, and tetraethylthiuram disulfide. The reaction is promoted either by a copper(I) catalyst or by irradiation with blue light in the presence of Eosin Y disodium salt.

  宝石-二氟有机锌试剂，其通过将CF 2片段插入C Zn键，与二乙基二黄原酮，二（苯并噻唑基）二硫化物和四乙基秋兰姆二硫化物偶联而制备。在曙红Y二钠盐存在下，通过铜（I）催化剂或通过蓝光照射促进反应。
• Nickel-Promoted Alkylative or Arylative Carboxylation of Alkynes
  作者：Masanori Takimoto、Kazuya Shimizu、Miwako Mori

  DOI：10.1021/ol016585z

  日期：2001.10.1

  terminal alkynes via a carbon dioxide fixation process was investigated. In the presence of a stoichiometric amount of a zero-valent nickel complex, the reaction of alkynes with CO2 gave a nickelacycle, which was reacted with various organozinc reagents under very mild conditions to provide beta,beta'-disubstituted, alpha,beta-unsaturated carboxylic acids in a highly regio- and stereoselective manner

  [反应：请参见文字]。研究了镍通过二氧化碳固定过程促进的末端炔烃的烷基化或芳基化羧化反应。在化学计量的零价镍络合物的存在下，炔烃与CO2的反应产生了镍环，其在非常温和的条件下与各种有机锌试剂反应，以提供β，β'-二取代，α，β-不饱和键以高度区域选择性和立体选择性的方式生成羧酸。
• Access to Functionalized Quaternary Stereocenters via the Copper-Catalyzed Conjugate Addition of Monoorganozinc Bromide Reagents Enabled by <i>N</i>,<i>N-</i>Dimethylacetamide
  作者：Tyler J. Fulton、Phebe L. Alley、Heather R. Rensch、Adriana M. Ackerman、Cameron B. Berlin、Michael R. Krout

  DOI：10.1021/acs.joc.8b02201

  日期：2018.12.7

  reagents, readily obtained from alkyl bromides, display excellent reactivity with β,β-disubstituted enones and TMSCl in the presence of Cu(I) and Cu(II) salts to synthesize a variety of cyclic functionalized β-quaternary ketones in 38–99% yields and 9:1–20:1 diastereoselectivities. The conjugate addition features a pronounced improvement in DMA using monoorganozinc bromide reagents. A simple one-pot protocol

  易于从烷基溴化物中获得的单有机锌试剂，在存在铜（Ⅰ）和铜（Ⅱ）盐的情况下，与β，β-二取代的烯酮和TMScl具有优异的反应活性，可以在38-99的范围内合成各种环状官能化的β-季酮。 ％的收率和9：1–20：1的非对映选择性。使用溴化单有机锌试剂可显着改善共轭物的DMA。利用原位生成的单有机锌试剂的简单一锅操作方案可提供相当的产品产量。