3-(4-iodophenyl)propiolaldehyde | 1242772-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-iodophenyl)propiolaldehyde
• 英文别名: (4-iodophenyl)propargyl aldehyde；3-(4-Iodophenyl)prop-2-ynal
• CAS: 1242772-11-7
• 化学式: C₉H₅IO
• 分子量: 256.043
• InChiKey: WBEGHUQMSPMSST-UHFFFAOYSA-N

物化性质

• 沸点：
  314.9±25.0 °C(predicted)
• 密度：
  1.83±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-iodophenyl)propiolaldehyde 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 乙酸酐 、 sodium cyanoborohydride 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium bromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 37.0h， 生成
  参考文献：
  名称：

  醛的有机催化不对称反选择性迈克尔反应和高功能水戊烷的对映选择性合成的顺序还原/内酰胺化/ Pauson-Khand反应

  摘要：

  已开发出一种新方法，用于对具有四个高立体选择性（高达99％ee）的立体异构中心的高度官能化的水戊烯进行对映选择性合成。该过程将对映选择性有机催化抗选择性迈克尔加成反应与高效的一锅还原/内酯化/ Pauson-Khand反应序列结合在一起。通过X射线分析确认了产物的结构和绝对构型。

  DOI：

  10.1021/ol302527z
• 作为产物：
  描述：

  1-(4-碘苯基)-1-丙炔-3-醇 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以70%的产率得到3-(4-iodophenyl)propiolaldehyde
  参考文献：
  名称：

  伊凡诺夫反应/银（I）催化的酸化/原位脱水序列两步合成（Z）-3-芳基-5-（芳基亚甲基）丁烯内酯

  摘要：

  献给教授迪特尔·恩德斯（亚琛）在他70之际个生日 抽象的 开发了标题化合物的立体选择性合成。将α-锂化的芳基乙酸锂（“芳乙酸二价阴离子”）的不含己烷和胺的THF溶液醛醇加成到3-芳基丙炔中。这样得到的2,5-二芳基-3-羟基戊-4-yonic酸的抗-非对映异构体的优先级高达72:28 （27个实例+ 1个例外）。当在室温下用DMF中的Ag 2 CO 3（1–20 mol％）处理2.5天时，分别对混合物进行区域和立体选择性内酯化，然后进行原位脱水。从而用Z获得3-芳基-5-（芳基亚甲基）丁烯内酯-氧化的C ＝ C键的构型。它们的总产率在46％到83％之间（1个例外：28％）。三个3-芳基-5-（芳基亚甲基）丁烯内酯含有一个C–Br和/或C–I键。他们允许随后进行Pd催化的C–C偶联，从而提供了后续的丁烯内酯。 开发了标题化合物的立体选择性合成。将α-锂化的芳基乙酸锂（“芳乙酸二价阴离子”）的

  DOI：

  10.1055/s-0036-1588338

文献信息

• Rhodium-Catalyzed 1,1-Hydroacylation of Thioacyl Carbenes with Alkynyl Aldehydes and Subsequent Cyclization
  作者：Bingnan Zhou、Qiuyue Wu、Ziyang Dong、Jiaxi Xu、Zhanhui Yang

  DOI：10.1021/acs.orglett.9b01003

  日期：2019.5.17

  A rhodium-catalyzed 1,1-hydroacylation of thioacyl carbenes with alkynyl and alkenyl aldehydes and subsequent 6-endo-trig/dig cyclization are realized, giving structurally diverse 4H-thiopyran-4-ones and 2,3-dihydro-4H-thiopyran-4-ones in moderate to good yields. The oxidative addition of Rh(I) to aldehydes is proposed to be the turnover-limiting step. Manipulations of estrones demonstrate the applications

  实现了铑的羰基羰基与炔基和烯基醛催化的1,1-氢羰基化反应，随后进行了6-内-trig / dig环化反应，得到了结构上不同的4 H - thiopyran -4-ones和2,3-dihydro-4 H -thiopyran-4-ones，产量中等至良好。提出将Rh（I）氧化成醛是限制营业额的步骤。雌酮的操作证明了我们正式的（3 + 3）转环剂在天然产物的结构修饰中的应用。
• Synthesis of 3-trifluoromethylpyrazoles via trifluoromethylation/cyclization of α,β-alkynic hydrazones using a hypervalent iodine reagent
  作者：Guojing Ji、Xi Wang、Songnan Zhang、Yan Xu、Yuxuan Ye、Ming Li、Yan Zhang、Jianbo Wang

  DOI：10.1039/c4cc01280a

  日期：——

  A mild and efficient method for the synthesis of 3-trifluoromethylpyrazoles has been established via trifluoromethylation/cyclization of α,β-alkynic hydrazones using a hypervalent iodine reagent.

  已建立一种温和高效的方法，通过使用高价碘试剂对α，β-炔基腙酮进行三氟甲基化/环化反应合成3-三氟甲基吡唑。
• N,N′-Dibutylbarbituric acid as an acceptor moiety in push–pull chromophores
  作者：Milan Klikar、Filip Bureš、Oldřich Pytela、Tomáš Mikysek、Zdeňka Padělková、Alberto Barsella、Kokou Dorkenoo、Sylvain Achelle

  DOI：10.1039/c3nj00683b

  日期：——

  Twelve novel D–π–A chromophores with the N,N′-dibutylbarbituric acid acceptor, the N,N-dimethylamino donor and a systematically extended π-linker were synthesized. The extent of intramolecular charge-transfer, structure–property relationships and nonlinear optical properties were further investigated by X-ray analysis, electrochemistry, UV/Vis absorption spectra, calculations and EFISH experiments.

  合成了具有N，N'-二丁基巴比妥酸受体、N，N-二甲基氨基供体和系统性延长的π连接体的十二种新型D-π-A型色团。通过X射线分析、电化学、紫外/可见吸收光谱、计算和EFISH实验进一步研究了分子内电荷转移程度、结构-性质关系和非线性光学性质。
• Efficient One-Pot Preparation of Methylthio Arylbutadiynes by Double Elimination Protocol
  作者：Qiong Su、Hong Yan、Shi-Chao Gao、De-Xun Xie、Qing-Yun Cai、Guang Shao、Zhi-Hong Peng、De-Lie An

  DOI：10.1080/00397911.2012.729280

  日期：2013.10.2

  A novel and efficient method for preparation of methylthio arylbutadiynes (Ar-CC-CC-SCH3) was described, and a series of compounds have been expediently obtained by the one-pot protocol starting from methylthiomethyl phenyl sulfone (MP-S) and arylpropargyl aldehydes. The mechanism was discussed on the basis of trapping and characterization of key intermediates. The results from experiments indicated that the reaction involved the initial nucleophilic addition of MP-S to arylpropargyl aldehydes to produce an intermediate carrying two leaving groups and subsequent double elimination reactions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.
• Synthesis and spectroscopic study of phenylene–(poly)ethynylenes substituted by amino or amino/cyano groups at terminal(s): electronic effect of cyano group on charge-transfer excitation of acetylenic π-systems
  作者：Jing-Kun Fang、De-Lie An、Kan Wakamatsu、Takeharu Ishikawa、Tetsuo Iwanaga、Shinji Toyota、Shin-ichi Akita、Daisuke Matsuo、Akihiro Orita、Junzo Otera

  DOI：10.1016/j.tet.2010.05.016

  日期：2010.7

  To gain insight into substituent electronic effect on charge-transfer excitation of acetylenic pi-systems, phenylene-(poly)ethynylenes substituted by Ph2N or Ph2N/cyano groups were synthesized by combination of Sonogashira coupling and double elimination protocol of beta-substituted sulfones. These substituted phenyleneethynylenes showed large molar absorption coefficients epsilon, and emitted strong fluorescence upon UV light irradiation. Phenylene (poly)ethynylenes, which involve butadiyne or hexatriyne motifs, emitted fluorescence in remarkably lower fluorescence quantum yields Phi(F) as their polyethynylene motifs -(C C)(n)- expanded. The drastic decrease of fluorescence quantum yields Phi(F) were explained in terms of increasing nonradiative reaction rate constants k(nr), which had been determined by the corresponding fluorescence quantum yields Phi(F) and lifetime values tau. The emission underwent a large bathochromic shift in polar solvents because the charge-separated excited state is more stabilized than the ground state. Comparison of slope values rho in Lippert/Mataga plot for the Ph2N and Ph2N/cyano-substituted phenylene (poly)ethynylenes revealed that the latter underwent large change of dipole moments upon photo-excitation although highly expanded acetylenic pi-systems with cyano group did little. (C) 2010 Elsevier Ltd. All rights reserved.