methyl 4-(naphthalen-1-yl)-4-hydroxybut-2-ynoate | 943435-69-6

• 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-1-yl)but-2-ynoate；methyl (4R)-4-hydroxy-4-naphthalen-1-ylbut-2-ynoate
• CAS: 943435-69-6
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: KGYHFTHZVHWDGT-CQSZACIVSA-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

• 作为产物：
  描述：

  1-萘甲醛 、 丙炔酸甲酯 在 Dimethylzinc 、 ((1R,3S)-2,2-dimethyl-3-((morpholin-4-yl)-methyl)cyclopropyl)diphenylmethanol 作用下， 以 甲苯 为溶剂， 反应 26.0h， 以65%的产率得到methyl 4-(naphthalen-1-yl)-4-hydroxybut-2-ynoate
  参考文献：
  名称：

  高度对映选择性的锌/氨基醇催化的醛烷基化

  摘要：

  应对挑战：苯乙炔和丙酸甲酯对锌/氨基醇催化的末端炔烃对醛的对映选择性加成反应均有效，从而导致手性仲炔丙醇具有很高的对映选择性（参见方案）。

  DOI：

  10.1002/chem.200900070

文献信息

• Highly Enantioselective Zinc/Amino Alcohol-Catalyzed Alkynylation of Aldehydes
  作者：Jiang-Chun Zhong、Shi-Cong Hou、Qing-Hua Bian、Min-Min Yin、Ri-Song Na、Bing Zheng、Zhi-Yuan Li、Shang-Zhong Liu、Min Wang

  DOI：10.1002/chem.200900070

  日期：2009.3.16

  Meeting the challenge: The zinc/amino alcohol catalyzed enantioselective addition of terminal alkynes to aldehydes is effective with both phenylacetylene and methyl propiolate, leading to chiral secondary propargyl alcohols with very high enantioselectivity (see scheme).

  应对挑战：苯乙炔和丙酸甲酯对锌/氨基醇催化的末端炔烃对醛的对映选择性加成反应均有效，从而导致手性仲炔丙醇具有很高的对映选择性（参见方案）。
• Asymmetric Synthesis of γ-Hydroxy-α,β-acetylenic Esters Catalyzed by Oxazolidine-Titanium Complex
  作者：Jincheng Mao、Jun Guo

  DOI：10.1055/s-0029-1217712

  日期：2009.9

  An efficient catalytic system has been developed for the enantioselective reaction of alkynoates with aromatic aldehydes for the synthesis of optically active γ-hydroxy-α,β-acetylenic esters (with up to 81 % isolated yield and up to 84% enantioselectivity).

  已经开发了一种有效的催化系统，用于炔酸酯与芳香醛的对映选择性反应，用于合成光学活性 γ-羟基-α,β-炔酸酯（分离产率高达 81%，对映选择性高达 84%）。
• Highly enantioselective addition of methyl propiolate to aldehydes catalyzed by a titanium(IV) complex of a β-hydroxy amide
  作者：Tao Xu、Chao Liang、Yan Cai、Jian Li、Ya-Min Li、Xin-Ping Hui

  DOI：10.1016/j.tetasy.2009.11.022

  日期：2009.12

  Three chiral beta-hydroxy amide ligands were prepared by the reaction of benzyl chloride with amino alcohols derived from L-tyrosine. The titanium(IV) complex of chiral ligand 4a was found to be an effective catalyst for the asymmetric addition of methyl propiolate, to aliphatic and aromatic aldehydes. The gamma-hydroxy-alpha,beta-acetylenic esters were obtained in excellent enantiomeric excesses (up to 94% ee) under optimized conditions. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.
• 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.