methyl 4-(naphthalen-1-yl)-4-hydroxybut-2-ynoate | 876656-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 4-(naphthalen-1-yl)-4-hydroxybut-2-ynoate
• 英文别名: methyl 4-hydroxy-4-(naphthalen-4-yl)but-2-ynoate；Methyl 4-hydroxy-4-naphthalen-1-ylbut-2-ynoate；methyl 4-hydroxy-4-naphthalen-1-ylbut-2-ynoate
• CAS: 876656-47-2
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: KGYHFTHZVHWDGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(naphthalen-1-yl)-4-hydroxybut-2-ynoate 在 4-二甲氨基吡啶 、 三苯基膦氯金 、 水 、 silver trifluoromethanesulfonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 4-methoxy-1-(naphthalen-1-yl)-2,4-dioxobutyl benzoate
  参考文献：
  名称：

  Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates

  摘要：

  The At(I)-catalyzed regioselective hydration of gamma-acetoxy-alpha,beta-acetylinic ester by the assistance of a neighboring carbonyl group has beets developed. Varieties of simple primary, secondary, and tertiary gamma-acetoxy-alpha,beta-acetylinic esters, even those bearing sensitive functional group in the remote reaction sites, are selectively hydrated to the corresponding beta-keto esters. The reaction' tolerates a wide variety of other carboxylates, such as benzoates, propionates, acrylates, and pivalates, including chiral carboxylates with retention of the configuration. The broad substrate scope, including the derivatization of complex natural products and neutral and open air conditions, makes this atom economical approach very practical. O-18 labeling experiments disclose that the oxygen transposition occurs from the carboxylate group to the triple bond, not from water.

  DOI：

  10.1021/acs.joc.5b00400
• 作为产物：
  描述：

  1-萘甲醛 、 丙炔酸甲酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 生成 methyl 4-(naphthalen-1-yl)-4-hydroxybut-2-ynoate
  参考文献：
  名称：

  Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates

  摘要：

  The At(I)-catalyzed regioselective hydration of gamma-acetoxy-alpha,beta-acetylinic ester by the assistance of a neighboring carbonyl group has beets developed. Varieties of simple primary, secondary, and tertiary gamma-acetoxy-alpha,beta-acetylinic esters, even those bearing sensitive functional group in the remote reaction sites, are selectively hydrated to the corresponding beta-keto esters. The reaction' tolerates a wide variety of other carboxylates, such as benzoates, propionates, acrylates, and pivalates, including chiral carboxylates with retention of the configuration. The broad substrate scope, including the derivatization of complex natural products and neutral and open air conditions, makes this atom economical approach very practical. O-18 labeling experiments disclose that the oxygen transposition occurs from the carboxylate group to the triple bond, not from water.

  DOI：

  10.1021/acs.joc.5b00400

文献信息

• Highly Enantioselective Synthesis of γ-Hydroxy-α,β-acetylenic Esters Catalyzed by a β-Sulfonamide Alcohol
  作者：Li Lin、Xianxing Jiang、Weixia Liu、Li Qiu、Zhaoqing Xu、Jiangke Xu、Albert S. C. Chan、Rui Wang

  DOI：10.1021/ol070692x

  日期：2007.6.1

  concerns the asymmetric addition of methyl propiolate to aldehydes with 1,2-dimethoxyethane (DME) as additive and beta-sulfonamide alcohol titanium complex as a catalyst. The reactions proceeded under mild conditions and gave the highly functionalized chiral propargylic alcohols with high ee values and good yields. Differences between three types of ligands have also been discussed.

  这项工作涉及以1,2-二甲氧基乙烷（DME）为添加剂，以β-磺酰胺醇钛络合物为催化剂将丙酸甲酯不对称加成到醛中。反应在温和的条件下进行，得到具有高ee值和良好收率的高度官能化的手性炔丙醇。还讨论了三种类型的配体之间的差异。
• Robust eco-friendly protocol for the preparation of γ-hydroxy-α,β-acetylenic esters by sequential one-pot elimination–addition of 2-bromoacrylates to aldehydes promoted by LTMP in 2-MeTHF
  作者：Vittorio Pace、Laura Castoldi、Andrés R. Alcántara、Wolfgang Holzer

  DOI：10.1039/c2gc35305a

  日期：——

  An efficient and widely applicable preparation of γ-hydroxy-α,β-acetylenic esters is described by means of a one-pot dehydrobromination of a 2-bromoacrylate ester with LTMP followed by the electrophilic addition of the transient propiolate to different aldehydes in the eco-friendly solvent 2-MeTHF.

  一种高效且广泛适用的γ-羟基-α，β-炔烃制剂 酯类 用2-甲基丙烯酸酯与LTMP进行一锅脱氢溴化，然后亲电将瞬变丙酸酯加成至不同 醛类 在环保 溶剂 2-MeTHF。
• Highly Enantioselective Synthesis of γ-Hydroxy-α,β-acetylenic Esters by Asymmetric Alkyne Addition to Aldehydes
  作者：Ge Gao、Qin Wang、Xiao-Qi Yu、Ru-Gang Xie、Lin Pu

  DOI：10.1002/anie.200500469

  日期：2006.1
• Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates
  作者：Tapas R. Pradhan、Kishor L. Mendhekar、Debendra K. Mohapatra

  DOI：10.1021/acs.joc.5b00400

  日期：2015.6.5

  The At(I)-catalyzed regioselective hydration of gamma-acetoxy-alpha,beta-acetylinic ester by the assistance of a neighboring carbonyl group has beets developed. Varieties of simple primary, secondary, and tertiary gamma-acetoxy-alpha,beta-acetylinic esters, even those bearing sensitive functional group in the remote reaction sites, are selectively hydrated to the corresponding beta-keto esters. The reaction' tolerates a wide variety of other carboxylates, such as benzoates, propionates, acrylates, and pivalates, including chiral carboxylates with retention of the configuration. The broad substrate scope, including the derivatization of complex natural products and neutral and open air conditions, makes this atom economical approach very practical. O-18 labeling experiments disclose that the oxygen transposition occurs from the carboxylate group to the triple bond, not from water.
• Highly enantioselective catalytic methyl propiolate addition to both aromatic and aliphatic aldehydes
  作者：Jian Huang、Siping Wei、Li Wang、Chun Zhang、Shuangxun Li、Pingxian Liu、Xi Du、Qin Wang

  DOI：10.1016/j.tetasy.2016.03.009

  日期：2016.6

  The excellent catalytic effect on methyl propiolate addition to a wide range of aromatic and aliphatic aldehydes promoted by inexpensive and commercially available BINOL-based ligand is reported. The catalyst systems showed high yields and excellent enantioselectivities for aromatic aldehydes, and excellent yields and high enantioselectivities for aliphatic aldehydes. (C) 2016 Elsevier Ltd. All rights reserved.