2-(3,3-dimethylbut-1-yn-1-yl)benzoic acid chloride | 205250-15-3

• 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: 2-(3,3-dimethylbut-1-yn-1-yl)benzoic acid chloride
• 英文别名: 2-(3,3-Dimethylbut-1-ynyl)benzoyl chloride
• CAS: 205250-15-3
• 化学式: C₁₃H₁₃ClO
• 分子量: 220.699
• InChiKey: PYMMQUWBCVICAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  2-(3,3-dimethylbut-1-yn-1-yl)benzoic acid chloride 在 sodium hydrogen selenide 、 四丁基硫酸氢铵 作用下， 以 水 、 甲苯 为溶剂， 以70%的产率得到3-[2,2-Dimethyl-prop-(Z)-ylidene]-3H-benzo[c]selenophen-1-one
  参考文献：
  名称：

  （Z）-3-亚甲基硒代邻苯二甲酸酯和（z）-3-亚甲基亚硒基邻苯二酚的高效立体定向制剂

  摘要：

  （Z）-3- Methylideneselenophthalides 5A和（Z）-3- methylidenetellurophthalides 5B很容易通过2-乙炔基氯化物的区域选择性和立体选择性的反应来制备3分别hydroselenide钠和hydrotelluride钠以良好的收率。

  DOI：

  10.1002/jhet.5570350131
• 作为产物：
  描述：

  2-乙炔苯甲酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-(3,3-dimethylbut-1-yn-1-yl)benzoic acid chloride
  参考文献：
  名称：

  PhI(OCOCF₃)₂-Mediated Cyclization of o-(1-Alkynyl)benzamides: Metal-Free Synthesis of 3-Hydroxy-2,3-dihydroisoquinoline-1,4-dione

  摘要：

  The synthesis of an undocumented skeleton of 3-hydroxy-2,3-dihydroisoquinoline-1,4-diones has been discovered and reported. The reaction consists of an intramolecular cyclization of o-(1-alkynyl)benzamides in MeCN/H2O, mediated by metal-free, hypervalent reagent of PhI(OCOCF3)(2), followed by an oxidative hydroxylation reaction: The mechanism consisting of two pathways has been proposed and discussed:

  DOI：

  10.1021/acs.joc.5b00576

文献信息

• Reaction of 2-Alkynylbenzoyl Cyanides with Carboxylic Acids Producing Functionalized Indenones
  作者：Masahiro Murakami、Hiroshi Shimizu

  DOI：10.1055/s-2008-1078501

  日期：——

  2-Alkynylbenzoyl cyanides react with carboxylic acids via a cyclic allene intermediate to produce 2-acylamino-3-acylindenones in good yield. The high reactivity of the 2-acylamino moiety of the product for a substitution reaction can be utilized for the synthesis of fused heterocycles.

  2-炔基苯甲酰基氰化物通过环状丙二烯中间体与羧酸反应，以良好的收率生成 2-酰基氨基-3-酰基茚酮。产物的 2-酰氨基部分对取代反应的高反应性可用于合成稠合杂环。
• Ir(III)-Catalyzed Stereoselective Haloamidation of Alkynes Enabled by Ligand Participation
  作者：Seung Youn Hong、Junsoo Son、Dongwook Kim、Sukbok Chang

  DOI：10.1021/jacs.8b08134

  日期：2018.10.3

  Described herein is the application of a strategy of ligand participation for the Ir-catalyzed imido transfer into alkynes. On the basis of a stoichiometric [3 + 2] cycloaddition of Cp*Ir(III)(κ2- N, O-chelate) with alkynyl dioxazolone, a catalytic haloamidation was developed for the first time by employing [Cp*IrCl2]2 precatalyst and NaX salts (X = Cl or Br) as practical halide sources to furnish

  本文描述了配体参与策略在 Ir 催化的亚氨基转移到炔烃中的应用。在 Cp*Ir(III)(κ2-N, O-螯合物) 与炔基二恶唑酮的化学计量 [3 + 2] 环加成基础上，首次使用 [Cp*IrCl2]2 预催化剂开发了催化卤代酰胺化和 NaX 盐（X = Cl 或 Br）作为实用的卤化物来源，以提供具有优异立体选择性的合成通用 Z-（卤乙烯基）内酰胺。
• Copper(II)/DBU Relay Catalyzed Annulation of α-Carbonyl-γ-alkynyl Sulfoxonium Ylides for Accessing <i>N</i>-Sulfonamido 2<i>H</i>-Isoindoles
  作者：Peng Zhou、Wei-Tao Yang、Wen-Juan Hao、Bo Jiang

  DOI：10.1021/acs.orglett.3c03479

  日期：2023.12.1

  A copper(II)/DBU relay catalyzed annulation of α-carbonyl-γ-alkynyl sulfoxonium ylides as a new class of sulfoxonium ylide reagents with sulfonyl hydrazides is reported, enabling intramolecular oxygen migration to produce a series of N-sulfonamido 2H-isoindoles with good yields. The present annulation proceeded readily by combining the Cu(II)-catalyzed 6-endo-dig oxo-cyclization with the DBU-catalyzed

  报道了铜(II)/DBU中继催化α-羰基-γ-炔基亚砜叶立德成环作为一类新型亚砜叶立德试剂与磺酰肼的反应，使分子内氧迁移产生一系列N-磺酰胺基2H-异吲哚具有良好的产量。通过将 Cu(II) 催化的 6-内地物氧环化与 DBU 催化的异色烯骨架重排相结合，本环化很容易进行，从而形成多个新的化学键。
• PhI(OCOCF₃)₂-Mediated Cyclization of <i>o</i>-(1-Alkynyl)benzamides: Metal-Free Synthesis of 3-Hydroxy-2,3-dihydroisoquinoline-1,4-dione
  作者：Chao Yang、Xiang Zhang、Daisy Zhang-Negrerie、Yunfei Du、Kang Zhao

  DOI：10.1021/acs.joc.5b00576

  日期：2015.5.15

  The synthesis of an undocumented skeleton of 3-hydroxy-2,3-dihydroisoquinoline-1,4-diones has been discovered and reported. The reaction consists of an intramolecular cyclization of o-(1-alkynyl)benzamides in MeCN/H2O, mediated by metal-free, hypervalent reagent of PhI(OCOCF3)(2), followed by an oxidative hydroxylation reaction: The mechanism consisting of two pathways has been proposed and discussed:
• An efficient stereospecific preparation of (Z)-3-methylidene-selenophthalides and (z)-3-methylidenetellurophthalides
  作者：Haruki Sashida、Atsusbi Kawamukai

  DOI：10.1002/jhet.5570350131

  日期：1998.1

  (Z)-3-Methylideneselenophthalides 5A and (Z)-3-methylidenetellurophthalides 5B were easily prepared by the regioselective and stereoselective reaction of 2-ethynylbenzoyl chlorides 3 with sodium hydroselenide and sodium hydrotelluride in good yields, respectively.

  （Z）-3- Methylideneselenophthalides 5A和（Z）-3- methylidenetellurophthalides 5B很容易通过2-乙炔基氯化物的区域选择性和立体选择性的反应来制备3分别hydroselenide钠和hydrotelluride钠以良好的收率。