Methyl 2-[3-[3-(2-methoxycarbonylphenyl)prop-2-ynylsulfanyl]prop-1-ynyl]benzoate | 1421759-82-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 2-[3-[3-(2-methoxycarbonylphenyl)prop-2-ynylsulfanyl]prop-1-ynyl]benzoate
• 英文别名: methyl 2-[3-[3-(2-methoxycarbonylphenyl)prop-2-ynylsulfanyl]prop-1-ynyl]benzoate
• CAS: 1421759-82-1
• 化学式: C₂₂H₁₈O₄S
• 分子量: 378.449
• InChiKey: DNOLNWSJJZYBHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-[3-[3-(2-methoxycarbonylphenyl)prop-2-ynylsulfanyl]prop-1-ynyl]benzoate 在 sodium tetrahydroborate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 6.0h， 生成 [9-[2-(Hydroxymethyl)phenyl]-2,2-dioxo-1,3-dihydrobenzo[f][2]benzothiol-5-yl]methanol
  参考文献：
  名称：

  Asymmetric Garratt–Braverman Cyclization: A Route to Axially Chiral Aryl Naphthalene–Amino Acid Hybrids

  摘要：

  We report the first example of a highly diastereoselective Garratt-Braverman cyclization leading to the synthesis of chiral aryl naphthalene amino acid hybrids in excellent yields. The stereogenecity in the amino acid has induced high diastereoselectivity for the reaction. Computations based on density functional theory indicated a lower activation free energy barrier for the M isomer as compared to that for the P diastereomer (Delta G = 3.48 kcal/mol). Comparison of the recorded CD spectrum of the product with the calculated one also supported the preferential formation of the M diastereomer.

  DOI：

  10.1021/jo500771g

文献信息

• Asymmetric Garratt–Braverman Cyclization: A Route to Axially Chiral Aryl Naphthalene–Amino Acid Hybrids
  作者：Tapobrata Mitra、Saibal Jana、Sharmila Pandey、Prabuddha Bhattacharya、Uttam K. Khamrai、Anakuthil Anoop、Amit Basak

  DOI：10.1021/jo500771g

  日期：2014.6.20

  We report the first example of a highly diastereoselective Garratt-Braverman cyclization leading to the synthesis of chiral aryl naphthalene amino acid hybrids in excellent yields. The stereogenecity in the amino acid has induced high diastereoselectivity for the reaction. Computations based on density functional theory indicated a lower activation free energy barrier for the M isomer as compared to that for the P diastereomer (Delta G = 3.48 kcal/mol). Comparison of the recorded CD spectrum of the product with the calculated one also supported the preferential formation of the M diastereomer.