2-苄基己酸甲酯 | 78308-00-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-苄基己酸甲酯
• 英文名称: Methyl 2-benzylhexanoate
• CAS: 78308-00-6
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: PBKIWSGSRJCKCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-苯基丙酸 在 乙酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.0h， 生成 2-苄基己酸甲酯
  参考文献：
  名称：

  A novel type of structurally simple nonpeptide inhibitors for α-chymotrypsin. Induced-fit binding of methyl 2-allyl-3-benzene-propanoate to the S2 subsite pocket

  摘要：

  Unexpectedly, methyl and benzyl esters of 2-allyl-3-benzenepropanoic acid were found to be not substrates but potent competitive inhibitors for alpha-chymotrypsin. The inhibitory property of the structurally simple nonpeptidic compounds is ascribed to their high binding affinity to the enzyme at the S-2 rather than S-1 subsite pocket. These inhibitors exist in a flexible form in solution, but as they bind to the enzyme bulky contrained conformers present in a minute concentration play an important role, forming tighter enzyme-inhibitor complexes by binding to the large hydrophobic S-2 pocket. The contrained conformers are thought to be resulted from intramolecular CH/pi interactions between a vinylic proton and the aromatic pi-electron cloud in the inhibitor molecules. These compounds constitute novel examples of the induced-fit binding inhibitor of possibly simplest structure. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10038-4

文献信息

• Indium-catalyzed coupling reaction between silyl enolates and alkyl chlorides or alkyl ethers
  作者：Yoshihiro Nishimoto、Takahiro Saito、Makoto Yasuda、Akio Baba

  DOI：10.1016/j.tet.2009.03.106

  日期：2009.7

  The coupling reactions of alkyl chlorides with silyl enolates catalyzed by InBr3, and the coupling reactions of alkyl ethers with silyl enolates catalyzed by the combined Lewis acid of InBr3/Me3SiBr are described. In both reaction systems, various types of silyl enolates were used to give corresponding α-alkylated esters, ketones, carboxylic acids, amides, thioesters, and aldehydes.

  描述了烷基氯化物与InBr 3催化的烯醇硅酸酯的偶联反应，以及烷基醚与InBr 3 / Me 3 SiBr的路易斯酸催化的烯醇硅酸酯的偶联反应。在两个反应系统中，都使用了各种类型的甲硅烷基烯酸酯，以生成相应的α-烷基化的酯，酮，羧酸，酰胺，硫代酯和醛。
• Acylations and alkylations of an ester enolate in high yield at room temperature of polystyrene supports
  作者：Young H. Chang、Warren T. Ford

  DOI：10.1021/jo00331a045

  日期：1981.8
• Use of highly crosslinked polystyrene supports for acylation and alkylation of an ester enolate at room temperature
  作者：Young H. Chang、Warren T. Ford

  DOI：10.1021/jo00339a022

  日期：1981.12
• A novel type of structurally simple nonpeptide inhibitors for α-chymotrypsin. Induced-fit binding of methyl 2-allyl-3-benzene-propanoate to the S2 subsite pocket
  作者：Dong H. Kim、Zhi-Hong Li、Soo Suk Lee、Jeong-il Park、Sang J. Chung

  DOI：10.1016/s0968-0896(97)10038-4

  日期：1998.2

  Unexpectedly, methyl and benzyl esters of 2-allyl-3-benzenepropanoic acid were found to be not substrates but potent competitive inhibitors for alpha-chymotrypsin. The inhibitory property of the structurally simple nonpeptidic compounds is ascribed to their high binding affinity to the enzyme at the S-2 rather than S-1 subsite pocket. These inhibitors exist in a flexible form in solution, but as they bind to the enzyme bulky contrained conformers present in a minute concentration play an important role, forming tighter enzyme-inhibitor complexes by binding to the large hydrophobic S-2 pocket. The contrained conformers are thought to be resulted from intramolecular CH/pi interactions between a vinylic proton and the aromatic pi-electron cloud in the inhibitor molecules. These compounds constitute novel examples of the induced-fit binding inhibitor of possibly simplest structure. (C) 1998 Elsevier Science Ltd. All rights reserved.