1-(benzyloxy)-3-phenethoxypropan-2-ol | 74423-40-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1-(benzyloxy)-3-phenethoxypropan-2-ol
• CAS: 74423-40-8
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: TXNUEABVBHTSRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  21.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(benzyloxy)-3-phenethoxypropan-2-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-(Benzyloxy)-3-phenethoxypropan-2-one
  参考文献：
  名称：

  Exploration of flexible phenylpropylurea scaffold as novel cardiac myosin activators for the treatment of systolic heart failure

  摘要：

  A series of flexible urea derivatives have been synthesized and demonstrated as selective cardiac myosin ATPase activator. Among them 1-phenethyl-3-(3-phenylpropyl)urea (1, cardiac myosin ATPase activation at 10) mu M = 51.1%; FS = 18.90; EF = 12.15) and 1-benzyl-3-(3-phenylpropyl)urea (9, cardiac myosin ATPase activation = 53.3%; FS = 30.04; EF = 18.27) showed significant activity in vitro and in vivo. The change of phenyl ring with tetrahydropyran-4-yl moiety viz., 1-(3-phenylpropy1)-3-((tetrahydro-2H-pyran-4-y1) methyl)urea (14, cardiac myosin ATPase activation = 81.4%; FS = 20.50; EF = 13.10), and morpholine moiety viz., 1-(2-morpholinoethyl)-3-(3-phenylpropyl)urea (21, cardiac myosin ATPase activation = 44.0%; FS = 24.79; EF = 15.65), proved to be efficient to activate the cardiac myosin. The potent compounds 1, 9, 14 and 21 were found to be selective for cardiac myosin over skeletal and smooth myosins. Thus, these urea derivatives are potent scaffold to develop as a newer cardiac myosin activator for the treatment of systolic heart failure. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.04.005
• 作为产物：
  描述：

  苯乙醇 在 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 19.25h， 生成 1-(benzyloxy)-3-phenethoxypropan-2-ol
  参考文献：
  名称：

  Exploration of flexible phenylpropylurea scaffold as novel cardiac myosin activators for the treatment of systolic heart failure

  摘要：

  A series of flexible urea derivatives have been synthesized and demonstrated as selective cardiac myosin ATPase activator. Among them 1-phenethyl-3-(3-phenylpropyl)urea (1, cardiac myosin ATPase activation at 10) mu M = 51.1%; FS = 18.90; EF = 12.15) and 1-benzyl-3-(3-phenylpropyl)urea (9, cardiac myosin ATPase activation = 53.3%; FS = 30.04; EF = 18.27) showed significant activity in vitro and in vivo. The change of phenyl ring with tetrahydropyran-4-yl moiety viz., 1-(3-phenylpropy1)-3-((tetrahydro-2H-pyran-4-y1) methyl)urea (14, cardiac myosin ATPase activation = 81.4%; FS = 20.50; EF = 13.10), and morpholine moiety viz., 1-(2-morpholinoethyl)-3-(3-phenylpropyl)urea (21, cardiac myosin ATPase activation = 44.0%; FS = 24.79; EF = 15.65), proved to be efficient to activate the cardiac myosin. The potent compounds 1, 9, 14 and 21 were found to be selective for cardiac myosin over skeletal and smooth myosins. Thus, these urea derivatives are potent scaffold to develop as a newer cardiac myosin activator for the treatment of systolic heart failure. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.04.005

文献信息

• Nucleophilic Reactivity of Ethers Against Terminal Epoxides in the Presence of BF₃: A Mechanistic Study
  作者：Aytekin Kose、Ramazan Altundas、Hasan Seçen、Yunus Kara

  DOI：10.1002/hlca.201200438

  日期：2013.7

  In the presence of BF3, a series of symmetrical and unsymmetrical ethers reacted with epichlorohydrin and 2‐[(benzyloxy)methyl]oxirane, two terminal epoxides, to afford 1‐alkoxy‐3‐chloropropan‐2‐ol and 1‐alkoxy‐3‐(benzyloxy)propan‐2‐ol. The cleavage of unsymmetrical ethers occurred via an SN2 or SN1 mechanism. Secondary epoxides did not give similar ring‐opening products.

  在BF 3存在下，一系列对称和不对称醚与表氯醇和2-[[（苄氧基）甲基]环氧乙烷，两个末端环氧化物反应，生成1-烷氧基-3-氯丙烷-2-醇和1-烷氧基- 3-（苄氧基）丙-2-醇。不对称醚的裂解发生经由一个小号Ñ 2或小号Ñ 1家机构。仲环氧化物没有给出类似的开环产物。