(methoxymethoxy)propanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (methoxymethoxy)propanone
• 英文别名: 4,6-dioxaheptanone；1-(Methoxymethoxy)propan-2-one
• 化学式: C₅H₁₀O₃
• 分子量: 118.133
• InChiKey: BCOAOCSNNMLOKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (methoxymethoxy)propanone 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  α-Fluoroallenoate Synthesis via N-Heterocyclic Carbene-Catalyzed Fluorination Reaction of Alkynals

  摘要：

  The first catalytic alpha-fluoroallenoate synthesis is described. With a suitable combination of N-heterocyclic carbene precatalyst, base, and fluorine reagent, the reaction proceeded smoothly to yield a wide range of alpha-fluoroallenoates with excellent chemoselectivity. These substituted alpha-fluorinated allenoates have been synthesized for the first time, and they are versatile synthetic intermediates toward other useful fluorine-containing building blocks.

  DOI：

  10.1021/acs.orglett.5b03615
• 作为产物：
  描述：

  氯甲基甲基醚 、 羟基丙酮 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 (methoxymethoxy)propanone
  参考文献：
  名称：

  Heteroatom-Assisted Isomerization of Oxiranes to Allylic Alcohols Promoted by Bases

  摘要：

  The isomerization of alkoxy-substituted oxiranes to hydroxy-substituted ene ethers promoted by mixed metal bases has been investigated. The structure of the oxirane substrate (the number, the position, and the type of alkyl substituents on the ring) plays an important role in driving the stereoselectivity of the reaction. Disubstituted oxiranes show a predictable preference for the E-ene ether while trisubstituted substrates give either a mixture of stereoisomers or the E-ene ether exclusively, depending on the location of the third alkyl substituent.

  DOI：

  10.1021/jo00096a020

文献信息

• Enantioselective Cyanosilylation of Ketones with Amino Acid/BINAP/Ruthenium(II)-Lithium Phenoxide Catalyst Systems
  作者：Masato Uemura、Nobuhito Kurono、Yusuke Sakai、Takeshi Ohkuma

  DOI：10.1002/adsc.201200027

  日期：2012.7.9

  Enantioselective reactions of simple ketones, α,α‐ and β,β‐dialkoxy ketones, and α‐alkoxy ketones with trimethylsilyl cyanide catalyzed by the bimetallic systems of amino acid/BINAP/ruthenium(II) complexes and lithium phenoxide have been studied [BINAP=2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl]. The Ru(PhGly)2(BINAP)‐lithium phenoxide system showed high enantioselectivity for the reaction of acetophenone

  研究了简单的酮，α，α和β，β-二烷氧基酮和α-烷氧基酮与氨基酸/ BINAP /钌（II）配合物和二氧化锂的双金属体系催化的三甲基甲硅烷基氰化物的对映选择性反应[BINAP = 2,2'-双（二苯基膦基）-1,1'-联萘基]。Ru（PhGly）2（BINAP）-苯酚锂体系对苯乙酮衍生物的反应具有很高的对映选择性，从而可以提供高达90％ee的氰化产物[PhGly =苯基甘氨酸]。对于二烷氧基酮和α-烷氧基酮的氰基硅烷化反应，Ru（t -Leu ）2（BINAP）-苯酚氧化锂系统表现出最佳的催化剂性能，可生产ee高达99％ee和98％的氰醇衍生物ee分别[ t -Leu =叔亮氨酸]。在最佳情况下，出色的催化活性导致反应完全转化，底物与催化剂的摩尔比（S / C）为10,000。
• 10.1021/acsmedchemlett.4c00078
  作者：Williams, David R.、Taylor, Levin、Miter, Gabriel A.、Sheiman, Johnathan L.、Wallace, Joseph M.、Allen, Matthew R.、Kohler, Rachel、Medeiros, Claudia

  DOI：10.1021/acsmedchemlett.4c00078

  日期：——

  Methodology is described for the synthesis of C6 derivatives of raloxifene, a prescribed drug for the treatment and prevention of osteoporosis. Studies have explored the incorporation of electron-withdrawing substituents at C6 of the benzothiophene core. Efficient processes are also examined to introduce hydrogen bond donor and acceptor functionality. Raloxifene derivatives are evaluated with in vitro

  描述了雷洛昔芬 C 6衍生物的合成方法，雷洛昔芬是一种用于治疗和预防骨质疏松症的处方药。研究探索了在苯并噻吩核的 C 6处吸电子取代基的掺入。还研究了引入氢键供体和受体功能的有效过程。通过体外测试评估雷洛昔芬衍生物，以确定雌激素受体 (ER) 结合亲和力和 MC3T3 细胞中的基因表达。
• α-Fluoroallenoate Synthesis via N-Heterocyclic Carbene-Catalyzed Fluorination Reaction of Alkynals
  作者：Xu Wang、Zijun Wu、Jian Wang

  DOI：10.1021/acs.orglett.5b03615

  日期：2016.2.5

  The first catalytic alpha-fluoroallenoate synthesis is described. With a suitable combination of N-heterocyclic carbene precatalyst, base, and fluorine reagent, the reaction proceeded smoothly to yield a wide range of alpha-fluoroallenoates with excellent chemoselectivity. These substituted alpha-fluorinated allenoates have been synthesized for the first time, and they are versatile synthetic intermediates toward other useful fluorine-containing building blocks.
• Heteroatom-Assisted Isomerization of Oxiranes to Allylic Alcohols Promoted by Bases
  作者：Alessandro Mordini、Sabina Pecchi、Giuseppe Capozzi、Antonella Capperucci、Alessandro Degl'Innocenti、Gianna Reginato、Alfredo Ricci

  DOI：10.1021/jo00096a020

  日期：1994.8

  The isomerization of alkoxy-substituted oxiranes to hydroxy-substituted ene ethers promoted by mixed metal bases has been investigated. The structure of the oxirane substrate (the number, the position, and the type of alkyl substituents on the ring) plays an important role in driving the stereoselectivity of the reaction. Disubstituted oxiranes show a predictable preference for the E-ene ether while trisubstituted substrates give either a mixture of stereoisomers or the E-ene ether exclusively, depending on the location of the third alkyl substituent.