5-hexyn-1-yl methoxymethyl ether | 137648-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-hexyn-1-yl methoxymethyl ether
• 英文别名: 6-(methoxymethoxy)-1-hexyne；6-(Methoxymethoxy)hex-1-yne
• CAS: 137648-92-1
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: UMWGAVVLGWYCIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-hexyn-1-yl methoxymethyl ether 在 吡啶 、 chromium(VI) oxide 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 7,7-difluoro-8-oxo-5-decyn-1-yl acetate
  参考文献：
  名称：

  Synthesis of partially fluorinated analogs of (Z)-5-decenyl acetate: probes for hydrophobic interaction in pheromone reception

  摘要：

  Selective regiochemical introduction of fluorines into methyl and methylene positions of (Z)-5-decenyl acetate provides analogues to probe the hydrophobicity requirements of the pheromone receptor site in the turnip moth, Agrotis segetum. Perfluorobutyl-, difluoromethylene-, trifluoromethyl-, and tetrafluoroethylene-containing analogues have been synthesized and chemically characterized.

  DOI：

  10.1021/jo00027a025
• 作为产物：
  描述：

  5-己炔-1-醇 、 氯甲基甲基醚 在 sodium hydride 作用下， 生成 5-hexyn-1-yl methoxymethyl ether
  参考文献：
  名称：

  Synthesis of partially fluorinated analogs of (Z)-5-decenyl acetate: probes for hydrophobic interaction in pheromone reception

  摘要：

  Selective regiochemical introduction of fluorines into methyl and methylene positions of (Z)-5-decenyl acetate provides analogues to probe the hydrophobicity requirements of the pheromone receptor site in the turnip moth, Agrotis segetum. Perfluorobutyl-, difluoromethylene-, trifluoromethyl-, and tetrafluoroethylene-containing analogues have been synthesized and chemically characterized.

  DOI：

  10.1021/jo00027a025

文献信息

• Cobaloxime-catalyzed hydration of terminal alkynes without acidic promoters
  作者：Shengtai Hou、Hongjian Yang、Bin Cheng、Hongbin Zhai、Yun Li

  DOI：10.1039/c7cc03919k

  日期：——

  Cobaloxime (Co(dmgBF2)2·2H2O), an inexpensive first-row transition-metal complex, catalyzed hydration of terminal alkynes gave the corresponding methyl ketones in good to excellent yields under neutral conditions (additional protic acids and silver salts are not required). A wide range of functional groups, such as allyl ether, benzyl ethers, carboxylic esters, imides, amides, nitro, and halogens,

  钴肟（Co（dmgBF 2）2 ·2H 2 O），一种廉价的第一行过渡金属络合物，在末端炔烃的催化水合下，在中性条件下以良好或优异的收率得到了相应的甲基酮（另外的质子酸和银盐是不需要）。耐受各种官能团，例如烯丙基醚，苄基醚，羧酸酯，酰亚胺，酰胺，硝基和卤素。温和的反应条件以及廉价的特征和催化剂的容易获得性很好地解决了炔烃水合领域中的当前挑战。
• Enantioselective hydrophosphinylation of 1-alkenylphosphine oxides catalyzed by chiral strong Brønsted base
  作者：Azusa Kondoh、Sho Ishikawa、Masahiro Terada

  DOI：10.1039/d0ob01778g

  日期：——

  A catalytic enantioselective addition of diarylphosphine oxides to 1-alkenyl(diaryl)phosphine oxides was achieved by using a chiral ureate as a chiral strong Brønsted base catalyst. The reaction followed by the reduction of phosphine oxide moieties provided chiral 1,2-diphosphinoalkanes, which are a family of useful chiral ligands for asymmetric transition metal catalysis.

  通过使用手性脲酸酯作为手性强布朗斯台德碱催化剂，将二芳基膦氧化物催化对映选择性加成到1-烯基（二芳基）膦氧化物上。反应随后还原氧化膦部分提供了手性1，2-二膦基烷烃，其是用于不对称过渡金属催化的有用的手性配体家族。
• Iterative Approach to Oligo(arylenevinylene)s Containing Tetrasubstituted Vinylene Units
  作者：Naoki Ishida、Yasuhiro Shimamoto、Masahiro Murakami

  DOI：10.1021/ol1011136

  日期：2010.7.16

  Monodispersed oligo(arylenevinylene)s containing tetrasubstituted vinylene units were stereoselectively synthesized in an efficient manner by iteration of two different kinds of palladium-catalyzed reactions.

  通过重复两种不同类型的钯催化反应，以有效方式立体选择性地合成了含有四取代亚乙烯基单元的单分散低聚（亚芳基亚乙烯基）。
• PROCESS FOR PREPARING AN ALKOXYMETHYL ALKYNYL ETHER COMPOUND HAVING A TERMINAL TRIPLE BOND
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20210198172A1

  公开（公告）日：2021-07-01

  The present invention provides a process for preparing an alkoxymethyl alkynyl ether compound having a terminal triple bond of the following formula (4): H—C≡C(CH 2 ) a OCH 2 OCH 2 R (4), wherein R represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and “a” represents an integer of 1 to 10, the method comprising subjecting an alkynol compound having a terminal triple bond of the following formula (1): H—C≡C(CH 2 ) a OH (1), wherein “a” is as defined above, to an alkoxymethylation with a halomethyl alkyl ether compound of the following formula (3): RCH 2 OCH 2 X (3), wherein X represents a halogen atom, and R is as defined above, in the presence of a dialkylaniline compound of the following formula (2): [CH 3 (CH 2 ) b ][CH 3 (CH 2 ) c ]NC 6 H 5 (2), wherein b and c represent, independently of each other, an integer of 0 to 9, to form the alkoxymethyl alkynyl ether compound (4) having a terminal triple bond.

  本发明提供了一种制备具有以下式(4)的末端三键的烷氧甲基炔基醚化合物的方法：H—C≡C(CH2)aOCH2OCH2R (4)，其中R代表氢原子、具有1至9个碳原子的n-烷基基团或苯基，而“a”代表1至10的整数，所述方法包括将具有以下式(1)末端三键的炔醇化合物进行烷氧甲基化，其中H—C≡C(CH2)aOH (1)，其中“a”如上所定义，与具有以下式(3)的卤甲基烷醚化合物进行反应：RCH2OCH2X (3)，其中X代表卤素原子，R如上所定义，在存在以下式(2)的二烷基苯胺化合物的情况下进行，[CH3(CH2)b][CH3(CH2)c]NC6H5(2)，其中b和c独立地代表0至9的整数，以形成具有末端三键的烷氧甲基炔基醚化合物(4)。
• Process for preparing an alkoxymethyl alkynyl ether compound having a terminal triple bond
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US11384041B2

  公开（公告）日：2022-07-12

  The present invention provides a process for preparing an alkoxymethyl alkynyl ether compound having a terminal triple bond of the following formula (4): H—C≡C(CH2)aOCH2OCH2R (4), wherein R represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and “a” represents an integer of 1 to 10, the method comprising subjecting an alkynol compound having a terminal triple bond of the following formula (1): H—C≡C(CH2)aOH (1), wherein “a” is as defined above, to an alkoxymethylation with a halomethyl alkyl ether compound of the following formula (3): RCH2OCH2X (3), wherein X represents a halogen atom, and R is as defined above, in the presence of a dialkylaniline compound of the following formula (2): [CH3(CH2)b][CH3(CH2)c]NC6H5 (2), wherein b and c represent, independently of each other, an integer of 0 to 9, to form the alkoxymethyl alkynyl ether compound (4) having a terminal triple bond.

  本发明提供了一种制备具有下式(4)末端三键的烷氧基甲基炔基醚化合物的工艺：H-C≡C(CH2)aOCH2OCH2R(4)，其中 R 代表氢原子、具有 1 至 9 个碳原子的正烷基或苯基，且 "a "代表 1 至 10 的整数，该方法包括使具有下式(1)的末端三键的炔醇化合物：H-C≡C(CH2)aOH(1)，其中 "a "如上定义，用下式(3)的卤代甲基烷基醚化合物进行烷氧基甲基化：RCH2OCH2X(3)，其中 X 代表卤素原子，R 如上定义，在下式(2)的二烷基苯胺化合物存在下进行烷氧基甲基化：[CH3(CH2)b][CH3(CH2)c]NC6H5(2)，其中 b 和 c 各自代表 0 至 9 的整数，形成具有末端三键的烷氧基甲基炔基醚化合物 (4)。