4-Prop-2-ynyloxy-but-2-ynoic acid methyl ester | 211561-85-2

• 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: 4-Prop-2-ynyloxy-but-2-ynoic acid methyl ester
• 英文别名: 2-Butynoic acid, 4-(2-propynyloxy)-, methyl ester；methyl 4-prop-2-ynoxybut-2-ynoate
• CAS: 211561-85-2
• 化学式: C₈H₈O₃
• 分子量: 152.15
• InChiKey: CUIRYCXFZWQCJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Prop-2-ynyloxy-but-2-ynoic acid methyl ester 在 N-碘代丁二酰亚胺 、 silver nitrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以44%的产率得到Methyl 4-(3-iodoprop-2-ynoxy)but-2-ynoate
  参考文献：
  名称：

  Synthesis of Bicyclic p-Diiodobenzenes via Silver-Catalyzed Csp-H Iodination and Ruthenium-Catalyzed Cycloaddition

  摘要：

  Highly substituted iodobenzenes were efficiently and regioselectively synthesized from readily available 1,6-diynes via two-step process consisting of silver-catalyzed Csp-H iodination and subsequent ruthenium-catalyzed [2+2+2] cycloaddition of resultant iododiynes. Some of the obtained iodobenzenes were subjected to palladium-catalyzed C-C bond-forming reactions such as Mizoroki-Heck reaction, Sonogashira reaction, and Suzuki-Miyaura coupling, giving highly conjugated molecules.

  DOI：

  10.1021/ja061619p
• 作为产物：
  描述：

  4-Prop-2-ynoxybut-2-ynoic acid 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 4-Prop-2-ynyloxy-but-2-ynoic acid methyl ester
  参考文献：
  名称：

  摘要：

  DOI：

  10.1002/1099-0690(200107)2001:13<2507::aid-ejoc2507>3.0.co;2-p

文献信息

• One-pot synthesis of benzolactones and lactams via a cobalt-catalyzed regioselective [2 + 2 + 2] cocyclotrimerization of alkynyl alcohols and amines with propiolates
  作者：Hong-Tai Chang、Masilamani Jeganmohan、Chien-Hong Cheng

  DOI：10.1039/b509731b

  日期：——

  An efficient method for the synthesis of benzolactones and benzolactams via a cobalt-catalyzed [2 + 2 + 2] cocyclotrimerization of alkynyl alcohols and alkynyl amines with propiolates is described.

  描述了一种高效的方法，通过钴催化的[2 + 2 + 2]共聚三聚反应，将炔醇和炔胺与丙炔酸盐合成苯内酯和苯内酰胺。
• Oxidative addition reactions and stereochemistry on rhodium/4,5-bis(2-oxazolinyl)xanthene complexes
  作者：Hirofumi Uchimura、Jun-ichi Ito、Seiji Iwasa、Hisao Nishiyama

  DOI：10.1016/j.jorganchem.2006.04.040

  日期：2007.1

  The oxidative addition reactions on 4,5-bis(2-oxazolinyl)-(2,7-di-tert-butyl-9,9-dimethyl)-9H-xanthene (Xabox)/rhodium(I) complex were examined using chloroacetate and substituted diynes to give stereoselectively the corresponding methoxycarbonylmethyl-rhodium(III) complex and rhodacyclopentadiene complexes, respectively. The rhodacycle complex 7 catalyzed the cyclotrimerization of the diynes and alkynes

  使用以下方法检测了在4,5-双（2-恶唑啉基）-（2,7-二叔丁基-9,9-二甲基）-9 H - an吨（Xabox）/铑（I）络合物上的氧化加成反应氯乙酸盐和取代的二炔，分别立体选择性地得到相应的甲氧基羰基甲基-铑（III）配合物和Rhodacyclopentadiene配合物。罗丹环配合物7催化二炔和炔烃的环三聚反应，得到芳烃衍生物。
• Highly Regio- and Chemoselective [2 + 2 + 2] Cycloaddition of Electron-Deficient Diynes with Allenes Catalyzed by Nickel Complexes:  A Novel Entry to Polysubstituted Benzene Derivatives
  作者：Muthian Shanmugasundaram、Ming-Si Wu、Masilamani Jeganmohan、Chih-Wei Huang、Chien-Hong Cheng

  DOI：10.1021/jo0203084

  日期：2002.11.1

  Diynes 1a-c [X(CH(2)Ctbd1;CCO(2)Me)(2): X = (CH(2))(2), 1a, X = CH(2), 1b and X = O, 1c] undergo [2 + 2 + 2] ene-diyne cycloaddition reactions with a variety of allenes (n-butylallene 2a, phenylallene 2b, (4-chlorophenyl)allene 2c, (4-bromophenyl)allene 2d, (3-methoxyphenyl)allene 2e, 1-naphthylallene 2f, cyclohexylallene 2g and cyclopentylallene 2h) in the presence of Ni(dppe)Br(2) and Zn powder in

  Diynes 1a-c [X（CH（2）Ctbd1; CCO（2）Me）（2）：X =（CH（2））（2），1a，X = CH（2），1b和X = O， 1c]与各种丙二烯（正丁基丙二烯2a，苯丙二烯2b，（4-氯苯基）丙二烯2c，（4-溴苯基）丙二烯2d，（3-甲氧基苯基）]进行[2 + 2 + 2]烯-二炔环加成反应Ni（dppe）Br（2）和Zn粉在CH（3）CN中在80°C下存在8h的条件下，在8h的条件下，在8°C的条件下，在8°C的条件下，在80°C的条件下将8h的烯丙基2e，1-萘烯丙基2f，环己烯丙基2g和环戊烯丙基2h） -l的产量好到极好。在相似的反应条件下，不对称二炔5a-c（HCtbd1; CCH（2）XCH（2）Ctbd1; CCO（2）Me）与丙二烯2反应，以73-86％的收率独家提供相应的间位异构体6a-g 。催化反应具有高度的区域选择性和完全的化学选择性。该
• Synthesis of arylboronates via Cp*RuCl-catalyzed cycloaddition of alkynylboronates
  作者：Yoshihiko Yamamoto、Kozo Hattori、Jun-ichi Ishii、Hisao Nishiyama

  DOI：10.1016/j.tet.2006.02.068

  日期：2006.5

  In the presence of 5-10 mol% Cp*RuCI(cod), 1,6- and 1,7-diynes were allowed to react with an ethynylboronate at ambient temperature to give rise to bicyclic arylboronates in 64-93% isolated yields. 1,6-Diynes bearing a boronate terminal also underwent cycloaddition with monoalkynes to give the corresponding bicyclic arylboronates. (c) 2006 Elsevier Ltd. All rights reserved.